Related Products of 1904-31-0,Some common heterocyclic compound, 1904-31-0, name is 1-Methyl-1H-pyrazol-3-amine, molecular formula is C4H7N3, 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.
97 Preparation of N.N-dicyclopropyl-6-ethyl- 1 -methyl -4-( 1 -methyl- 1H- pyrazol-3-ylamino)-1.6-dihydroimidazo[4.5-dlpyrrolo[2.3-blpyridine-7-carboxamide[00465] To a vial containing 1 -methyl- lH-pyrazol-3 -amine (11.89 mg, 0.122 mmol), Pd2(dba)3 (4.67 mg, 5.10 muiotaetaomicron), Xantphos (5.90 mg, 10.20 muiotaetaomicron), and cesium carbonate (100 mg, 0.306 mmol) was added 4-bromo-N,N-dicyclopropyl-6-ethyl-l- methyl-l,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridine-7-carboxamide (example 97A, 41.0 mg, 0.102 mmol) in DME (1020 muKappa). The reaction mixture was sparged with argon for 5 min, the vial was capped, and the reaction mixture was heated at 60 °C for 4 h and 80 °C for 16h. The reaction mixture was concentrated in vacuo. The crude residue was purified by flash column chromatography using an Isco 40 g column eluting with 0 – 5percent MeOH/ (3/4(3/4 followed by additional purification with preparative HPLC. N,N-Dicyclopropyl-6-ethyl-l-methyl-4-(l -methyl- lH-pyrazol-3 – ylamino)-l,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridine-7-carboxamide (13 mg, 0.030 mmol, 29.5percent yield) was isolated as a white solid.[00466] MS (ESI) m/z 419.3 (M+H) [00467] 1H NMR (400 MHz, CHLOROFORM-d) delta ppm 8.17 (s, 1 H), 7.64 (s, 1 H), 7.31 (d, 1H, J= 2.26 Hz), 7.16 (d, 1 H, J= 2.26 Hz), 6.86 (s, 1 H), 4.65 (q, 2 H, J = 7.03 Hz), 4.01 (s, 3 H), 3.85 (s, 3H), 2.78 – 2.87 (m, 2 H), 1.49 (t, 3 H, J= 7.15 Hz), 0.81 – 0.89 (m, 4 H), 0.71 – 0.80 (m, 4 H)
The synthetic route of 1904-31-0 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; PURANDARE, Ashok V.; GREBINSKI, James W.; HART, Amy; INGHRIM, Jennifer; SCHROEDER, Gretchen; WAN, Honghe; WO2011/28864; (2011); A1;,
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