Category: 89830-98-8

Related Products of 89830-98-8, A common heterocyclic compound, 89830-98-8, name is 5-Cyclopropyl-1H-imidazole, molecular formula is C6H8N2, 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.

A suspension 4-bromo-N-(5-(4-cyclopropyl-4H-1,2,4-triazol-3-yl)thiophen-3-yl)picolinamide (63 mg, 0.16 mmol), 4-cyclopropyl imidazole (35 mg, 0.24 mmol), Cu2O (1.2 mg, 0.0081 mmol), 4,7-dimethoxy-1,10-phenanthroline (5.9 mg, 0.024 mmol, (or 8-hydroxy-quinoline may be used as the ligand with comparable results), cesium carbonate (116 mg, 0.36 mmol), and PEG-3350 (32 mg) in butyronitrile (1 mL) was heated at 100¡ã C. for 16 hours. The solvent was removed and the residue was purified by reverse-phase HPLC to 4-(4-cyclopropyl-1H-imidazol-1-yl)-N-(5-(4-cyclopropyl-4H-1,2,4-triazol-3-yl)thiophen-3-yl)picolinamide as a white powder (9.2 mg, 0.377 mmol, 13percent yield). C21H19N7OS. 418.2 (M+1). 1H NMR (DMSO) delta 11.42 (s, 1H), 8.77 (s, 1H), 8.60 (s, 1H), 8.54 (s, 1H), 8.37 (d, J=2 Hz, 1H), 8.33 (d, J=2 Hz, 1H), 8.04 (d, J=1 Hz, 1H), 7.97 (dd, J=2, 5 Hz, 1H), 7.85 (s, 1H), 3.55-3.59 (m, 1H), 1.85-1.88 (m, 1H), 1.22-1.26 (m, 2H), 1.11-1.13 (m, 2H), 0.82-0.86 (m, 2H), 0.72-0.75 (m, 2H).

The synthetic route of 89830-98-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Gilead Sciences, Inc.; US2012/4267; (2012); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 89830-98-8, name is 5-Cyclopropyl-1H-imidazole, A new synthetic method of this compound is introduced below., Recommanded Product: 5-Cyclopropyl-1H-imidazole

A mixture of 9-iodo-1-methyl-3,4,7,8- tetrahydro-[1,4]diazepino[7,1-a]isoquinoline-2,5-dione (30 mg, 81 muGammaetaomicronIota) in DCE (2 mL) is treated with POCI3 (15 mu, 0.16 mmol) and heated to 100 ¡ãC for 3 h. The mixture was then allowed to cool to RT, poured onto H20 and extracted with DCM, The org. phases were dried over Na2S0 , filtered and concentrated in vacuo. The brown residue obtained was taken up in DCE (2 mL) and 4-cyclopropyl-1H-imidazole (31 mg, 0.28 mmol) and pyridine (20 mu, 0.24 mmol) were then added. The mixture was heated to 100 ¡ãC for 4.5 h, and then allowed to cool to RT, poured onto H20 and extracted with DCM. The org. layers were then dried over Na2S04, filtered and concentrated in vacuo. Filtration through a pad of Si02 (AcOEt) afforded a brown solid that was purified by SFC (column: Diol 5 muiotaeta, 250 x 30 mm, 60A, Princeton; euent: 13percent MeOH/C02 for 1 min, then from 13percent MeOH/C02 to 18percent MeOH/C02 in 6 min; then from 18percent MeOH/C02 to 50percent MeOH/C02 in 1 min; flow 100 mL/min; UV detection at 220 nm) to give the title compound (11 mg) as a white powder. UPLC-MS: MS 459.0 (M+hf ); UPLC rt 0.98 min.

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; NOVARTIS AG; BEHNKE, Dirk; CARCACHE, David; ERTL, Peter; KOLLER, Manuel; ORAIN, David; WO2014/30128; (2014); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 89830-98-8, name is 5-Cyclopropyl-1H-imidazole, A new synthetic method of this compound is introduced below., HPLC of Formula: C6H8N2

[00641] A mixture of Example 134b (100 mg, 0.235 mmol), Example 134c (108 mg, 1.0 mmol), K2C03 (162 mg, 1.175 mmol), Cul (11 mg, 0.058 mmol) in dry DMSO (2 mL) was heated at 125¡ãC for 24 h. The reaction was cooled to r.t., and water (25 mL) was added. The resulting mixture was stirred for 5 min, and filtered to give the crude product, which was purified by prep-HPLC (by Ultimate XB-C18, 50 x 250 mm, 10 muetaiota, speed: 80 mL/min, eluent: A/B = H20/CH3C = from 75/25 to 45/55 over 30 min. Ret. Time =: 24.94 min), followed by prep-TLC (DCM/MeOH = 10/1) to give the desired product Example 134 (1.2 mg, yield 1percent) as a white solid. LC-MS [M+l]+ = 454.0. NMR (400 MHz, Chloroform-d) delta 11.80 (s, 1H), 8.23-8.15 (m, 3H), 8.04 (s, 1H), 7.97 (t, J= 7.9 Hz, 1H), 7.83 (s, 1H), 7.50 (s, 2H), 7.12 (s, 1H), 4.83 (t, J= 8.9 Hz, 1H), 4.58 (s, 2H), 4.41 (t, J= 6.9 Hz, 1H), 3.81 (s, 2H), 2.88 (s, 2H), 1.96 (d, J= 38.7 Hz, 1H), 0.89 (d, J= 7.0 Hz, 2H), 0.83 (s, 2H).

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; FRONTHERA U.S. PHARMACEUTICALS LLC; JIN, Bohan; DONG, Qing; HUNG, Gene; (214 pag.)WO2019/51265; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 89830-98-8, name is 5-Cyclopropyl-1H-imidazole, 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 89830-98-8, Computed Properties of C6H8N2

A mixture of 3-bromo-5-(trifluoromethyl)aniline (0.48 g, 2.0 mmol), 4-cyclopropyl-lH- imidazole (0.26g, 2.4 mmol), K2CO3 (0.35g, 2.5 mmol), CuI (57 mg, 0.30 mmol), and 8- hydroxyquinoline (44 mg, 0.30 mmol) in dry DMSO (2 mL) in a microwave tube was cooled to -78deg;C, and degassed by vacuum and refilled with N2 for three times. The mixture was heated at1200C overnight. The mixture was cooled to 40-500C and 14percent aq. NH4OH was added. The mixture was stirred at 40-500C for 1 h. After cooling, the mixture was diluted with water, and extracted with ethyl acetate (3×15 mL). The combined organic layers were dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by flash chromatography on a silica gel column (5percent MeOH in CH2Cl2) to afford the crude product (0.41 g). LCMS: (M+H)+= 268.3.

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-Cyclopropyl-1H-imidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SYNTECH SOLUTION LLC; CHEN, Yongsheng; WO2010/96395; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 89830-98-8, name is 5-Cyclopropyl-1H-imidazole, 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. SDS of cas: 89830-98-8

To a stirred solution of 9-(2H- 1 ,2,3-triazol-2-y)-3,4,7,8-tetrahydro-[1 ,4]diazepino[7,1-a]isoquinoine-2,5-dione (97 mg, 0.328 mmol) in 1 ,2-dichloroethane (3 mL) was added POCI3 (0.061 mL, 0.657 mmol) at rt and the resulting suspension was stirred at 100¡ãC for 35 min. The reaction mixture was cooled to rt and concentrated under reduced pressure to dryness. For complete removal of POCI3 the residue was taken up in toluene and the solvent was evaporated under reduced pressure. The residue was dried under high vacuo at rt. The resulting crude choro intermediate was dissolved in 1 ,2-dichloroethane (3 ml_), 4- cyclopropyl-1 H-imidazole (107 mg, 0.985 mmol) was added and the mixture was stirred at 100¡ãC for 2h. The reaction mixture was allowed to warm to rt and diluted with DCM. Saturated aqueous NaHC03 solution was added and the mixture was extracted twice with DCM. The combined organic layers were washed with brine, dried with sodium sulfate, filtered and the solvent was removed under reduced pressure. The crude product was purified by flash-column chromatography over silicagel (Biotage Isolera Four, eluent: pure DCM for 3 min, then from 0percent MeOH in DCM to 5percent MeOH in DCM in 14 min, 5percent MeOH in DCM for 3 min) to yield a yellow foam. Further purification by SFC (column: 2-Ethylpyridine 5 mutauiota, 250 x 30 mm, 60A, Princeton; eluent: 8percent MeOH/C02 for 1 min, then from 8percent MeOH/C02 to 13percent MeOH/C02 in 6 min ; flow 100 ml_ min ; U V detection at 220 n m) gave the title compound as slightly yellow foam (21 mg). UPLC-MS: MS 386.2 (M+hT); UPLC rt 0.86 min. 1H NMR (400 MHz, DMSO-d6) delta ppm 0.58 – 0.70 (m, 2 H), 0.74 – 0.82 (m, 2 H), 1.74 – 1.86 (m, 1 H), 2.91 (t, J=5.75 Hz, 2 H), 3.75 (t, J=5.&7 Hz, 2 H), 4.25 (s, 2 H), 7.22 (s, 1 H), 7.43 (s, 1 H), 7.54 – 7.63 (m, 1 H), 7.76 (d, J=8.80 Hz, 1 H), 8.10 (s, 1 H), 8.14 – 8.21 (m, 3 H).

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

Reference:
Patent; NOVARTIS AG; BEHNKE, Dirk; CARCACHE, David; ERTL, Peter; KOLLER, Manuel; ORAIN, David; WO2014/30128; (2014); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 89830-98-8, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 89830-98-8 as follows.

J-1 a (4.84 g; 44.8 mmol) in TH F (60 mL) was added dropwise to a suspension of NaH (1 .97 g; 49.2 mmol) in TH F (200 mL) at 0¡ãC under N2. The mixture was stirred at RT for 30 min and SEM-CI (9.9 mL; 55.9 mmol) in THF(20 mL) was added dropwise at 0¡ãC. The mixture was stirred at RT under N2 for 16 h. Water was added and the product was extracted with DCM. The organic layer was dried over MgS04, filtered and concentrated under reduced pressure. The crude was purified by preparative LC (Irregular SiOH 20-45 [Jim , 150g Merck, Mobile phase Gradient from 50percent DCM, 50percent heptane to 100percent DCM). The fractions containing pure compound were combined and the solvent was removed under reduced pressure to give 6.6 g of J-1 b as a yellow oil (62percent).Mixture of 2 regioisomers : 70/30Minoritory regioisomer : 1H NMR (DMSO-de, 400MHz) : 5(ppm) 7.64 (s, 1 H), 6.56 (s, 1 H), 5.34 (s, 1 H), 3.45 (t, J = 8.08 Hz, 2H), 1 .73-1 .78 (m, 1 H), 0.80-0.86 (m, 2H), 0.72-0.74 (m, 2H), 0.52-0.57 (m, 2H), -0.04 (s, 9H).Majoritory regioisomer :1H NMR (DMSO-de, 400MHz) : 5(ppm) 7.56 (s, 1 H), 6.94 (s, 1 H), 5.20 (s, 1 H), 3.43 (t, J = 8.08 Hz, 2H), 1 .73-1 .78 (m, 1 H), 0.80-0.86 (m, 2H), 0.72-0.74 (m, 2H), 0.56-0.62 (m, 2H), -0.04 (s, 9H).

According to the analysis of related databases, 89830-98-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; JANSSEN R&D IRELAND; BONFANTI, Jean-Francois; DOUBLET, Frederic Marc Maurice; EMBRECHTS, Werner; FORTIN, Jerome Michel Claude; MC GOWAN, David Craig; MULLER, Philippe; RABOISSON, Pierre Jean-Marie Bernard; WO2013/68438; (2013); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 89830-98-8, name is 5-Cyclopropyl-1H-imidazole, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 5-Cyclopropyl-1H-imidazole

Step 2: 2-(4-cyclopropyl-1H-imidazol-1-yl)-9-(oxazol-5-yl)-7,8-dihydro-[1,4]diazepino[7,1-a]isoquinolin-5(4H)-one A mixture of 9-(oxazol-5-yl)-3,4,7,8-tetrahydro-[1,4]diazepino[7,1-a]isoquinoline-2,5-dione (180 mg, 0.61 mmol) in DCE (10 mL) was treated with POCl3 (114 muL, 1.22 mmol) and heated to 100¡ã C. for 1 h. The mixture was then allowed to cool to RT, poured onto cold H2O and extracted with DCM. The org. phases were dried over Na2SO4, filtered and concentrated in vacuo. The brown residue obtained was taken up in DCE (5 mL) and 4-cyclopropyl-1H-imidazole (79 mg, 0.73 mmol) and pyridine (148 muL, 1.83 mmol) were then added. The mixture was heated to 100¡ã C. for 1 h, and then allowed to cool to RT, poured onto H2O and extracted with DCM. The org. layers were then dried over Na2SO4, filtered and concentrated in vacuo. Purification by SFC (column: 2-Ethylpyridine 5 mum, 250*30 mm, 60A, Princeton; eluent: 9percent MeOH/CO2 for 1 min, then from 9percent MeOH/CO2 to 14percent MeOH/CO2 in 6 min; then from 14percent MeOH/CO2 to 50percent MeOH/CO2 in 1 min; flow 100 mL/min; UV detection at 220 nm) afforded the title compound (7 mg) as pale brown solid. UPLC-MS: MS 386.1 (M+H+); UPLC rt 0.79 min. 1H NMR (400 MHz, CHLOROFORM-d): delta ppm 0.78 (m, 2H); 0.81-0.87 (m, 2H); 1.79-1.93 (m, 1H); 3.14 (t, J=6.02 Hz, 2H); 3.94 (t, J=6.15 Hz, 2H); 4.38 (br. s., 2H); 6.66 (s, 1H); 7.20 (s, 1H); 7.30 (s, 1H); 7.42-7.60 (m, 1H); 7.77 (d, J=7.78 Hz, 1H); 7.74 (d, J=8.03 Hz, 1H); 7.90 (s, 1H); 8.03 (s, 1H).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 89830-98-8.

Reference:
Patent; NOVARTIS AG; BEHNKE, Dirk; CARCACHE, David; ERTL, Peter; KOLLER, Manuel; ORAIN, David; US2014/57902; (2014); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 89830-98-8,Some common heterocyclic compound, 89830-98-8, name is 5-Cyclopropyl-1H-imidazole, molecular formula is C6H8N2, 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.

J-1 a (4.84 g; 44.8 mmol) in TH F (60 mL) was added dropwise to a suspension of NaH (1 .97 g; 49.2 mmol) in TH F (200 mL) at 0¡ãC under N2. The mixture was stirred at RT for 30 min and SEM-CI (9.9 mL; 55.9 mmol) in THF(20 mL) was added dropwise at 0¡ãC. The mixture was stirred at RT under N2 for 16 h. Water was added and the product was extracted with DCM. The organic layer was dried over MgS04, filtered and concentrated under reduced pressure. The crude was purified by preparative LC (Irregular SiOH 20-45 [Jim , 150g Merck, Mobile phase Gradient from 50percent DCM, 50percent heptane to 100percent DCM). The fractions containing pure compound were combined and the solvent was removed under reduced pressure to give 6.6 g of J-1 b as a yellow oil (62percent).Mixture of 2 regioisomers : 70/30Minoritory regioisomer : 1H NMR (DMSO-de, 400MHz) : 5(ppm) 7.64 (s, 1 H), 6.56 (s, 1 H), 5.34 (s, 1 H), 3.45 (t, J = 8.08 Hz, 2H), 1 .73-1 .78 (m, 1 H), 0.80-0.86 (m, 2H), 0.72-0.74 (m, 2H), 0.52-0.57 (m, 2H), -0.04 (s, 9H).Majoritory regioisomer :1H NMR (DMSO-de, 400MHz) : 5(ppm) 7.56 (s, 1 H), 6.94 (s, 1 H), 5.20 (s, 1 H), 3.43 (t, J = 8.08 Hz, 2H), 1 .73-1 .78 (m, 1 H), 0.80-0.86 (m, 2H), 0.72-0.74 (m, 2H), 0.56-0.62 (m, 2H), -0.04 (s, 9H). BuLi (1.6M in hexane)(1 1 mL; 17.6 mmol) was added to a solution of J-1 b (3.5 g; 14.7 mmol) in THF (60 mL) at -50¡ãC. The mixture was stirred at the sametemperature for 30 min and DMF (1 .7 mL; 22 mmol) was added. The mixture was warmed slowly to RT in 1 h and NH2OH,HCI (970 mg; 29.4 mmol) was added and the mixture was stirred at RT for 16h. Water was added and the product was extracted with DCM (3 times), washed with brine, dried over MgS04 and the solvent was removed under reduced pressure to give 4.1 g (quantitative yield) of the mixture of isomers K-1 as yellow oil.HPLC Rt (min) = 5.30, 5.41 and 5.90 ; MS M+ (H+): 282 (method V2002V2002) K-1 ( 3.1 g; 1 1 mmol) was dissolved in DCM (18 mL) and pyridine (19 mL) at RT. The mixture was cooled to 0¡ãC and TFAA (4.6 mL; 33 mmol) was added. The mixture was stirred at RT for 24h. The solvent was removed under reduced pressure and the residue was dissolved in AcOEt. The organic layer was washed with water and brine, dried over MgS04, filtered and the solvent was removed under reduced pressure. The crude was purified by preparative LC (irregular SiOH 15-40??? 90g merck, mobile phase Heptane/DCM 30/70 to DCM 100percent) to give 2.14 g of intermediate J-1 (73percent) as a mixture of two isomers.HPLC Rt (min) = 6.51 ; MS M+ (H+): 264 (method V2002V2002)

The synthetic route of 89830-98-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN R&D IRELAND; BONFANTI, Jean-Francois; DOUBLET, Frederic Marc Maurice; EMBRECHTS, Werner; FORTIN, Jerome Michel Claude; MC GOWAN, David Craig; MULLER, Philippe; RABOISSON, Pierre Jean-Marie Bernard; WO2013/68438; (2013); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 89830-98-8, name is 5-Cyclopropyl-1H-imidazole, A new synthetic method of this compound is introduced below., HPLC of Formula: C6H8N2

[0304] A mixture of Example 3j (600 mg, 2.4 mmol) and Example 3i (400 mg, 3.6 mmol), Cul (45 mg, 0.24 mmol), K3P04 (1 g, 4.8 mmol), 4,7-Dihydroxy-l, 10-phenanthroline(9 mg, 0.48 mmol), TBAB (386 mg, 1.2 mmol) in H20 (10 mL) under N2 was heated at 100¡ãC overnight. After cooling, the reaction mixture was filtered and concentrated under reduced pressure to give the crude and further purified by silica chromatography to give the product 200 mg as yellow solid.

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; FRONTHERA U.S. PHARMACEUTICALS LLC; JIN, Bohan; DONG, Qing; HUNG, Gene; (227 pag.)WO2018/151830; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 89830-98-8, name is 5-Cyclopropyl-1H-imidazole, 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 89830-98-8, Computed Properties of C6H8N2

2-bromo-4-(4-cyclopropyl-1H-imidazol-1-yl)pyridine (4a) To a mixture of 4-cyclopropyl-1H-imidazole (3.5 g, 32.37 mmol) and (2-bromopyridin-4-yl)boronic acid (7.18 g, 35.60 mmol) in MeOH (50 mL) was added Cu2O (463.12 mg, 3.24 mmol) in one portion at 20 C. under O2. The mixture was stirred at 20 C. for 10 min, then heated to 50 C. and stirred for 16 hours. LCMS showed one new peak with desired MS. The mixture was filtered and the filtrate was concentrated in vacuo. The residue was purified by flash silica gel chromatography (ISCO; 10 g SepaFlash Silica Flash Column, Eluent of 100% Ethyl acetate gradient 200 mL/min) to give 2-bromo-4-(4-cyclopropyl-1H-imidazol-1-yl)pyridine (4a). MS mass calculated for [M+1]+ (C11H10BrN3) requires m/z 264.0, LCMS found m/z 264.0; 1H NMR (400 MHz, MeOD) delta 8.39 (d, J=5.6 Hz, 1H), 8.32 (s, 1H), 7.94 (d, J=1.8 Hz, 1H), 7.66 (dd, J=2.0, 5.6 Hz, 1H), 7.53 (s, 1H), 1.93-1.85 (m, 1H), 0.93-0.84 (m, 2H), 0.82-0.71 (m, 2H).

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; Terns, Inc.; XU, Yingzi; HALCOMB, Randall; KIRSCHBERG, Thorsten A.; ROMERO, F. Anthony; (117 pag.)US2019/315767; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem