Some tips on 68282-53-1

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Methyl-1H-imidazole-4-carbaldehyde, its application will become more common.

Synthetic Route of 68282-53-1,Some common heterocyclic compound, 68282-53-1, name is 5-Methyl-1H-imidazole-4-carbaldehyde, molecular formula is C5H6N2O, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

COMPOUND 14. 1.2 : NnN-DIETHYL-4- {6-METHOXY-2-r (5-METHYL-1H- IMIDAZOL-4-YL . METHYL]-7-PHENOXY-1. 2e3. 4- TETRAHYDROISOQUINOLIN-1-YL} BENZAMIDE; To INTERMEDIATE 10.2. 1 (30 mg, 0.06 mmol) was added a solution of hydrochloric acid in 1,4-dioxane (4N, 0.5 mL) at room temperature. The reaction mixture was stirred for an hour then concentrated by a stream of nitrogen and dried under vacuum. The residue was re-dissolved in 1,2-dichloroethane (1.5 mL) and to this solution was added 4-methyl-lH-imidazole-5-carbaldehyde (-2eq, 0.12 mmol, 12 mg) and followed by sodium triacetoxyborohydride (4eq, 0.24 mmol, 50 mg). The reaction mixture was stirred for 20 hr then quenched with saturated aqueous sodium bicarbonate and extracted to dichloromethane (15 mL x 2). Excess aldehyde was removed by stirring the extracted dichloromethane with polymer supported hydrazine for 2 hr. The polymer was filtered off and the filtrate was concentrated and dried under vacuum. Product was purified by flash chromatography, using Si02 column with MeOH/DCM (10: 90) afford 17.9 mg (0.034 mmol, 60%) of COMPOUND 14. 1.2 as light yellow oil. 1H NMR (500 MHz, CDC13): b 1. 05 (br s, 3H), 1.18 (br s, 3H), 2.00 (s, 3H), 2.50-2. 98 (br m, 4H), 3.10 (br s, 2H), 3.28 (m ; 1H), 3.49 (br s, 2H), 3.52 (m, 1H), 3.72 (s, 3H), 4.45 (s, 1H), 6. 28 (s, 1H), 6.65 (s, 1H), 6.68-7. 20 (m, 9H), 7.26 (m, 1H). 13C NMR (125 MHz, CDC13) : 6 10.97, 13.09, 14.42, 28. 70,39. 65, 43. 68, 46.96, 49.24, 56.20, 67. 66,106. 00,112. 63,115. 47,116. 47,122. 02,126. 57, 129.91, 130.26, 131.76, 132.93, 136.34, 142. 69,145. 32, 150.37, 150.37, 171. 51. (+) LRESIMS m/z 525 (M+H) +.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Methyl-1H-imidazole-4-carbaldehyde, its application will become more common.

Reference:
Patent; ASTRAZENECA AB; WO2005/61484; (2005); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

The important role of C5H6N2O

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 68282-53-1, its application will become more common.

Some common heterocyclic compound, 68282-53-1, name is 5-Methyl-1H-imidazole-4-carbaldehyde, molecular formula is C5H6N2O, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. category: imidazoles-derivatives

Triphenylphosphine (47.64 g, 181.64 mmol) and diisopropyl azodicarboxylate (36.73 g, 181.64 mmol) were dissolved in tetrahydrofuran (120.00 mL) at 0 C under a nitrogen atmosphere, followed by sequential addition of compound 1 (10.00 g, 90.82 mmol) and n-propanol (10.91 g, 181.64 mmol). The mixture was warmed to 25 C and stirred for 12 hours under a nitrogen atmosphere. After completion of the reaction, dilute hydrochloric acid (1 M) was added to the mixture to adjust to pH = 1 and extracted with ethyl acetate (50 mL × 3). The aqueous phase was adjusted to pH = 13 with sodium hydroxide (1M) and extracted with ethyl acetate (50 mL × 4). The organic phases were combined, washed with saturated brine (50 mL 2), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The obtained residue was purified by column chromatography (petroleum ether: ethyl acetate = 20:1-5:1) to obtain the title compound BB-3H-2 ((12.00 g, pale-yellow oily liquid, yield: 27.60%). 1H NMR (400MHz,CDCl3) delta: 9.81 (s, 1H), 7.50 (s, 1H), 4.19 (t, J = 7.1 Hz, 2H), 2.49 (s, 3H), 1.98- 1.74 (m, 2H), 0.89 (t, J = 7.5 Hz, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 68282-53-1, its application will become more common.

Reference:
Patent; Medshine Discovery Inc.; LUO, Yunfu; BA, Yuyong; CHEN, Shuhui; (135 pag.)EP3567028; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Research on new synthetic routes about 5-Methyl-1H-imidazole-4-carbaldehyde

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Related Products of 68282-53-1, A common heterocyclic compound, 68282-53-1, name is 5-Methyl-1H-imidazole-4-carbaldehyde, molecular formula is C5H6N2O, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Example 29 3-(5-Methyl-3H-imidazol-4-ylmethylene)-4-piperidin-4-yl-1,3-dihydroindol-2-one, Acetic Acid Salt A mixture of 4-piperidin-4-yl-1,3-dihydroindol-2-one (124 mg, 0.57 mmol) and 5-methyl-3H-imidazole-4-carbaldehyde (62.8 mg, 0.57 mmol) in ethanol (3 mL) was stirred at room temperature for 2 days. The reaction was concentrated and the residue was column chromatographed (reverse phase) to give 23 mg of the title compound as a yellow acetic acid salt. 1H NMR (300 MHz, DMSO-d6) delta 13.89 (br s, 1H, NH), 11. 02 (br s, 1H, NH), 7.90 (s, 1H), 7.52 (s, 1H), 7.15 (t, J 7.8 Hz, 1H), 6.93 (d, J=7.8 Hz, 1H), 6.76 (d, J 7.8 Hz, 1H), 3.20 (m, 1H), 3.15 (m, 2H, CH2), 2.73 (m, 2H, CH2), 1.86 (m, 3H, CH3), 1.84 (m, 2H, CH2), 1.62 (m, 2H, CH2). MS m/z 309 [M++1].

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; Tang, Peng Cho; Wei, Chung Chen; Huang, Ping; Cui, Jingrong; US2002/187978; (2002); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Sources of common compounds: C5H6N2O

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Methyl-1H-imidazole-4-carbaldehyde, its application will become more common.

Reference of 68282-53-1,Some common heterocyclic compound, 68282-53-1, name is 5-Methyl-1H-imidazole-4-carbaldehyde, molecular formula is C5H6N2O, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

COMPOUND 12.1.55: N,N-DIETHYL-4-{7-[(4-METHYL-1H-IMIDAZOL-5- YL) METHYL1-6J. 8, 9-TETRAHYDROri31DIOXOLOr4, 5-F] ISOOUINOLIN-6- YL}BENZAMIDE; 4-Methyl-imidazole-5-carboxyaldehyde (76. 4 mg, 0.69 mmol) was added to a solution of INTERMEDIATE 5.1. 15 (122.6 mg, 0.35 mmol) in 1,2-dichloroethane (5 mL) and the reaction mixture stirred at room temperature for 10 min. Sodium triacetoxyborohydride (516 mg, 2.43 mmol) was added followed by N-methyl-2- pyrrolidinone (400 I1L) and the reaction mixture stirred at RT for 18 h. 1 N NaOH (5 mL) was added and the organic solvent removed in vacuo. The residue was extracted with EtOAc (3 x 20 mL) and the organic layer washed with water (20 mL). The organic layer was concentrated in vacuo and the residue purified by flash chromatography on Si02 column (EtOAc: MeOH 95: 5) to afford COMPOUND 12.1. 55 as an oil (35.6 mg, 23%). 1H NMR (500 MHz, CDC13) : 8 1.13 (br s, 3H), 1.25 (br s, 3H), 2.09 (s, 3H), 2.55 (m, 1H), 2. 78 (m, 1H), 3.09 (m, 1H), 3.28 (br s, 2H), 3.34-3. 40 (m, 2H), 3.55 (br s, 2H), 3.59 (d, J 13.5 Hz, 1H), 4. 58 (s, 1H), 5.96 (s, 1H), 6. 21 (d, J 8 Hz, 1H), 6.55 (d, J 8 Hz, 1H), 7.28-7. 32 (m, 4H), 7.36 (s, 1H) ; 13C NMR (125 MHz, CDCl3) : 8 11. 37, 13. 11, 14.42, 22.28, 39.61, 43.64, 45.72, 49.40, 67.41, 101. 30, 106.56, 117. 66,122. 17, 126.56, 129.73, 130.71, 131.73, 133.45, 136.22, 144.81, 145.28, 145.54, 171. 54; (+) LRESIMS m/z 447.20 [M+H] +.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Methyl-1H-imidazole-4-carbaldehyde, its application will become more common.

Reference:
Patent; ASTRAZENECA AB; WO2005/61484; (2005); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Simple exploration of 5-Methyl-1H-imidazole-4-carbaldehyde

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Adding a certain compound to certain chemical reactions, such as: 68282-53-1, name is 5-Methyl-1H-imidazole-4-carbaldehyde, belongs to imidazoles-derivatives compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 68282-53-1, SDS of cas: 68282-53-1

COMPOUND 12.1. 19: 4-f6, {6s7-DIMETHOXY-2-r (4-METHYL-lH-IMIDAZOL-5- YL)METHYL]-1,2,3,4-TETRAHYDROISOQUINOLIN-1-YL}-N,N- DIETHYLBENZAMIDE; INTERMEDIATE 5.1. 7 (50 mg, 0.14 mmol) and 4-methyl-5-imidazolecarbaldehyde (30 mg, 0.27 mmol) were dissolved in DCE (3.0 mL). After stirring for 10 min at room temperature, sodium triacetoxyborohydride (86 mg, 0.41 mmol) was added and the mixture was stirred for 18 h at room temperature. DCM and 1 M sodium hydroxide solution were added and the mixture was passed through a Whatman 1PS silicon-treated filter paper. The organic phase was evaporated and the crude product was purified by flash chromatography to yield the product (57 mg, 0.12 mmol, 91%). 1H NMR (500 MHz, CDC13): 1. 08, 1.22 (2 brs, 6H), 2.07 (s, 3H), 2.54, 2.72, 2.90, 3.06 (4 m, 4H), 3.25, 3.54 (2 brs, 4H), 3.39, 3.59 (2 d, J 13 Hz, 2H), 4.56 (s, 1H), 6.16, 6.59 (2 s, 2H), 7.29 (s, 4H), 8.38 (brs, lH). l3C NMR (125 MHz, CDC13) : 11.14, 13.43, 14.03, 28.07, 39.69, 43.67, 46.67, 49. 48, 56.04, 56.06, 67.48, 111.2, 112.0, 126.5, 129.9, 127.2, 127.3, 129.3, 130.2, 136.1, 133. 3, 145.9, 147.6, 147.7, 171. 8. (+) LRESIMS mlz 369 (100), 463 (35).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; ASTRAZENECA AB; WO2005/61484; (2005); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Extended knowledge of 68282-53-1

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Application of 68282-53-1, A common heterocyclic compound, 68282-53-1, name is 5-Methyl-1H-imidazole-4-carbaldehyde, molecular formula is C5H6N2O, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

COMPOUND 12.1. 60: N*N-DIETHYL-4-f6-METHOXY-2-r (5-METHYL-1H- IMIDAZOL-4-YL) METHYLI-7- (NEOPENTYLOXY-1, 2, 3, 4- TETRAHYDROISOOUINOLIN-1-YUBENZAMIDE; To a solution of INTERMEDIATE 7.1. 4 (18 mg, 0.0424 mmol), 4-methyl-1H- imidazole-5-carboxaldehyde (5.8 mg, 0.052 mmol, 1. 2eq) in 1,2-dichloroethane (2 mL) was added sodium triacetoxyborohydride (11.1 mg, 0.052 mmol). The reaction mixture was stirred at room temperature for overnight, then diluted with dichloromethane (5 mL), quenched with saturated aqueous sodium bicarbonate (0.5 mL) and separated. The organic phase was washed with brine (1 x 2 mL), dried (MgSO4) and filtered. To the filtrate ps-scavenger was added, stirred for 2hr and filtered. The filtrate was concentrated and purified by flash chromatography to give compound COMPOUND 12.1. 60 (15 mg, 0.0029 mmol, 68%) as colorless oil. lHNMR (500 MHz, CD2Cl2) : No. 0. 89 (s, 9H), 1.00 (br s, 3H), 1.24 (br s, 3H), 1.90 (s, 3H), 1.99 (s, 2H), 2.45 (m, 1H), 2.68 (m, 1H), 2. 82 (m, 2H), 3.15 (br s, 2H), 3.28 (m, 2H), 3.40 (br s, 2H), 3.70 (s, 3H), 4.45 (s, 1H), 6.10 (br s, 1H), 6.51 (s, 1H), 7.29-7. 33 (m, 4H), 8.18 (s, 1H). (+) LRESIMS m/z 519 [M+H] +.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; ASTRAZENECA AB; WO2005/61484; (2005); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Continuously updated synthesis method about 5-Methyl-1H-imidazole-4-carbaldehyde

Statistics shows that 5-Methyl-1H-imidazole-4-carbaldehyde is playing an increasingly important role. we look forward to future research findings about 68282-53-1.

Electric Literature of 68282-53-1, These common heterocyclic compound, 68282-53-1, name is 5-Methyl-1H-imidazole-4-carbaldehyde, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

COMPOUND 12.1. 57: NV-DIETHYL-4-f 5, 6, 7-TRIMETHOXY-2-r (4-METHYL- lH-IMIDAZOL-5-YL) METHYLl-1, 2 3, 4-TETRAHYDROISOQUINOLIN-1- YL}BENZAMIDE; 4-Methyl-imidazole-5-carboxyaldehyde (65.2 mg, 0.59 mmol) was added to a solution of INTERMEDIATE 5.1. 16 (117.9 mg, 0.30 mmol) in 1,2-dichloroethane (5 mL) and the reaction mixture stirred at room temperature for 10 min. Sodium triacetoxyborohydride (439 mg, 2.07 mmol) was added followed by N-methyl-2- pyrrolidinone (350, uL) and the reaction mixture stirred at RT for 16 h. 1 N NaOH (5 mL) was added and the organic solvent removed in vacuo. The residue was extracted with EtOAc (3 x 20 mL) and the organic layer washed with water (20 mL). The organic layer was concentrated in vacuo and the residue purified by flash chromatography on Si02 column (EtOAc: MeOH 95: 5) to afford COMPOUND 12.1. 57 as an oil (32.2 mg, 22%).’HNMR (500 MHz, CDCl3) : 8 1.11 (br s, 3H), 1.25 (br s, 3H), 2. 09 (s, 3H), 2.52 (m, 1H), 2.70 (dt, J6.5, 17 Hz, 1H), 2 : 81 (dt, J4. 5, 17 Hz, 1H), 3.05 (m, 1H), 3.27 (br s, 2H), 3.39 (m, 2H), 3.55 (br s, 1H), 3.59 (m, 1H), 3.60 (s, 3H), 3.85 (s, 3H), 3.89 (s, 3H), 4.56 (s, 1H), 6.00 (s, 1H), 7.28-7. 32 (m, 4H), 7.39 (s, 1H) ; 13C NMR (125 MHz, CDC13) : 6 11. 12, 13.11, 14.41, 22.43, 39.69, 43.65, 46.30, 49.22, 56.12, 60. 71, 61.03, 67.59, 107.92, 121. 56,126. 55,129. 87, 130. 31, 132.67, 133.31, 136.29, 140.75, 145.12, 150. 85, 151. 79,171. 51; (+) LRESIMS m/z 493.24 [M+H] +.

Statistics shows that 5-Methyl-1H-imidazole-4-carbaldehyde is playing an increasingly important role. we look forward to future research findings about 68282-53-1.

The important role of 5-Methyl-1H-imidazole-4-carbaldehyde

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Methyl-1H-imidazole-4-carbaldehyde, and friends who are interested can also refer to it.

Related Products of 68282-53-1, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 68282-53-1 name is 5-Methyl-1H-imidazole-4-carbaldehyde, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

To a solution of Apim (2.81 g, 22.5 mmol) in dry methanol (17 mL) was added 4-methyl-5-imidazolecarboxaldehyde (2.17 g, 22.5 mmol). The resulting light-yellow suspension was heated to reflux for 3 h. The suspension was dissolved completely after 5 min. The solution was then stirred overnight at room temperature. After 0.5 h the solution turned orange in colour. The solvent was removed under reduced pressure to give an orange oil, which, on standing for 3 weeks, yielded the orange solid (5) (3.10 g, yield 76 %). M.p. 113-115C. C11H15N5 (217.27): Calc. C, 60.81; H, 6.96; N, 32.23. Found: C, 60.60; H, 6.72; N, 31.35%. 1H NMR (d6-DMSO): delta=8.23 (s, 1H), 7.64 (s, 1H), 7.61 (s, 1H), 7.18 (s, 1H), 6.91 (s, 1H), 4.04 (t, 2H, J=7.2Hz), 3.42 (t, 2H, J=6.6Hz), 2.32 (s, 3H), 2.03 (p, 2H, J=6.9, 6.6Hz) ppm. 13C NMR (d6-DMSO): delta=137.2, 128.3, 119.3, 57.3, 48.5, 43.9, 32.1ppm. IR (KBr): nu=3113, 1643, 1529, 1452, 1395, 1354, 1233, 1110, 1082, 826, 747cm-1. LC/TCOF-MS: Calc. for C10H14N5 [M+1]+ 218.3. Found 218.1%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Methyl-1H-imidazole-4-carbaldehyde, and friends who are interested can also refer to it.

Introduction of a new synthetic route about 5-Methyl-1H-imidazole-4-carbaldehyde

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 5-Methyl-1H-imidazole-4-carbaldehyde, other downstream synthetic routes, hurry up and to see.

Reference of 68282-53-1, The chemical industry reduces the impact on the environment during synthesis 68282-53-1, name is 5-Methyl-1H-imidazole-4-carbaldehyde, I believe this compound will play a more active role in future production and life.

COMPOUND 14.1. 5: N*N-DIETHYL-4- {6-METHOXY-7-(4- METHOXYPHENOXY)-2-r (5-METHYL-lH-IMIDAZOL-4-YL) METHYL]-1 2, 3,4- TETRAHYDROISOQUINOLIN-1-YL} BENZAMIDE; To INTERMEDIATE 10.2. 3 (38 mg, 0.068 mmol) was added a solution of hydrogen chloride in 1, 4-dioxan (4M, 1 mL) at RT and the mixture was stirred for 1 hr. Solvent was removed by applying a stream of nitrogen and followed by under vacuum. The dried residue was re-dissolved in 1,2-dichloroethane (5 mL). To this solution were added 4-methyl-lH-imidazole-5-carboxaldehyde (9 mg, 0.0816 mmol, 1.2 eq) and sodium triacetoxyborohydride (43 mg, 0.2036 mmol, 3eq). The reaction mixture was stirred at room temperature for overnight and then quenched with saturated aqueous sodium bicarbonate (2 mL), extracted with ethyl acetate (2 x 10 mL). The combined extracts were washed with brine (2 x 5 mL), dried over MgSO4 and concentrated. Product was purified by flash chromatography to afford COMPOUND 14.1. 5 (11 mg, 0.020 mmol, 29%). 1HNMR (CDC13, 500 MHz): No. 1. 10 (br s, 3H), 1. 25 (br s, 3H), 2.11 (s, 3H), 2.58 (br m, 1H), 2.78 (br m, 1H), 2.96 (m, 1H), 3.07 (br m, 1H), 3.22 (br s, 2H), 3.36 (d, J 13 Hz, 1H), 3.54 (br s, 2H), 3.59 (d, J 13 Hz, 1H), 3.75 (s, 3H0, 3.82 (s, 3H), 4.50 (s, 1H), 6.27 (s, 1H), 6.58 (s, 1H), 6.73 (s, 3H), 7.22-7. 35 (m, 5H). 13C NMR (125 MHz, CDC13) : 8 10.94, 13.12, 14.44, 28.46, 39.67, 43.67, 46. 88, 49.13, 55.87, 56.24, 67.53, 112.49, 114.74, 118.26, 120.71, 126.52, 129.79, 130.79, 132. 91, 136.30, 144.17, 145.25, 149.95, 151.76, 155. 89, 171.52. (+) LRESIMS m/z 555 [M+H] +.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 5-Methyl-1H-imidazole-4-carbaldehyde, other downstream synthetic routes, hurry up and to see.

The origin of a common compound about 5-Methyl-1H-imidazole-4-carbaldehyde

The synthetic route of 5-Methyl-1H-imidazole-4-carbaldehyde has been constantly updated, and we look forward to future research findings.

These common heterocyclic compound, 68282-53-1, name is 5-Methyl-1H-imidazole-4-carbaldehyde, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. Recommanded Product: 68282-53-1

COMPOUND 12.1. 26: N,N-DIETHYL-4-{7-HYDROXY-6-METHOXY-2-[(5- METHYL-1H-IMIDAZOL-4-YL)METHYL]-1,2,3, 4- TETRAHYDROISOOUINOLIN-1-YL} BENZAMIDE; To a solution of INTERMEDIATE 5.1. 12 (56 mg, o. 158 mmol) in anhydrous dichloromethane (3.5 mL) was added 4-methyl-lH-imidazole-5-carboxaldehyde (2. 5eq, 43 mg, 0.395 mmol) and followed by sodium triacetoxyborohydride (4eq, 134 mg, 0.623 mmol). The reaction mixture was stirred at room temperature for 20hr then quenched with saturated aqueous sodium bicarbonate and extracted with ethyl acetate (2 x 20 mL), dried over MgS04. Solvent was removed and the residue purified by preparative column chromatography to give 60 mg (0.1339 mmol, 84%) of COMPOUND 12.1. 26 as a white solid. 1H NMR (500 MHz, CDC13) : 8 1.15 (br s, 3H), 1.30 (br s, 3H), 2.08 (s, 3H), 2.61 (m, 1H), 2.78 (m, 1H), 2.98 (m, 1H), 3.18 (m, 1H), 3. 36 (br s, 2H), 3.40 (d, J 10 Hz, 1H), 3. 58 (br s, 2H), 3. 68 (d, J 10 Hz, 1H), 3. 80 (s, 3H), 4.58 (s, 1H), 6.15 (s, 1H), 6.70 (s, 1H), 7.35 (d, J 8 Hz, 2H), 7.40 (d, J 8 Hz, 2H), 7.75 (s, 1H). 13C NMR (125 MHz, CDC13) : 5 9. 10, 12.00, 13.05, 27.75, 39.80, 43.80, 49.05, 55.25, 68.02, 111.15, 114.97, 125. 66,126. 13,127. 44,128. 00,129. 42, 129. 89, 133.19, 135.99, 144.60, 146.00, 146.82, 172.50. (+) LRESIMS m/z 449 (M+H)+.

The synthetic route of 5-Methyl-1H-imidazole-4-carbaldehyde has been constantly updated, and we look forward to future research findings.