Electric Literature of 20075-26-7, A common heterocyclic compound, 20075-26-7, name is 1-(Methoxymethyl)-1H-imidazole, molecular formula is C5H8N2O, 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.
The title compound was prepared as follows. To a solution of 1-methoxymethyl- imidazole (216 mg, 1. 95 MMOL) in dry THF (20 mi) AT-78 C was added slowly a solution of t- butyllithium (2. 4 ml of 1. 7 M in THF). After 20 minutes, ZNCI2 (663 mg, 4. 86 MMOL) was added, the mixture was allowed to warm to room temperature and stirred for another 60 min. 1- 4-AMINO-2- [1- (6-CHLORO-PYRIDINE-3-SULFONYL)-PIPERIDIN-4-YLAMINO]-THIAZOL-5-YL}-1-PHENYL- methanone (Example F21 ; 200 mg, 0. 390 MMOL) AND TETRAKIS (TRIPHENYLPHOSPHINO) PALLADIUM (0) (Pd (Ph3P) 4 ; 12 mg, 0. 013 MMOL) were added and the mixture REFLUXED under argon for 2 hours. The solvent was removed and a solution of the resultant residue in ethyl acetate was washed with 0. 1 NAOH, dried over MGS04, filtered, and concentrated. The resultant solid was dissolved in a solution of 38% HCI (10 ML), ethanol (15 MI), and H20 (15 ml) and REFLUXED for 2 hours. The solvent was removed and a solution of the resultant residue in ethyl acetate was washed with sat. NaHCO3, dried over MGS04, filtered, concentrated, and purified via preparative HPLC. The concentrate from fractions was dissolved in EtOAc, washed with sat NAHC03, dried over MGS04, filtered, and concentrated. The resultant solid was placed in acetonitrile (30 ML), water (90 ML), and 38% HCI (0. 5 mL) and evaporated to give 26 mg of white powder in 11 % yield. ‘H NMR (CD30D) : 8 9. 13 (d1H, J=2. 5 Hz), 8. 44 (dd, 1H, J=2. 5, 8. 3 Hz), 8. 23 (d, 1H, J=8. 3 Hz), 7. 78 (s, 2H), 7. 50-7. 40 (m, 1H), 7. 08-6. 97 (m, 2H), 4. 02-3. 90 (m, 3H), 2. 98-2. 87 (m, 2H), 2. 37-2. 13 (m, 2H), 1. 96-1. 78 (m, 2H). ESIMS (MH+) : 546. Anal. Calcd for C23H2, F2N703S2 O 2. 4 HCI * 1. 0 H2O # 0. 5 EtOAc : C, 43. 19 ; H, 4. 26 ; N, 14. 10 ; S, 9. 23. Found : C, 42. 85 ; H, 4. 67 ; N, 14. 50 ; S, 9. 27.
The synthetic route of 20075-26-7 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; PFIZER INC.; WO2004/74283; (2004); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem