Sodium borohydride → HCID 58465063, compound

Participants

Reaction Steps

5-Amino-2-(2,6-difluorophenyl)-N-(1-methyl-5-(4-oxocyclohexyl)-1H-pyrazol-4-yl)thiazole-4-carboxamide (57 mg, 0.13 mmol), prepared according to the procedures provided in Example 347, was dissolved in methanol (2 mL). Sodium borohydride (15.1 mg, 0.40 mmol) was added. The mixture was stirred at RT for 1 h, quenched with sat. NaHCO3 and extracted with ethyl acetate three times. Combined organic layers were concentrated and purified via reverse phase HPLC to give 361. 1H NMR (400 MHz, DMSO) δ 8.69 (s, 1H), 7.61-7.48 (m, 2H), 7.46 (s, 2H), 7.26 (dd, J=14.5, 5.8 Hz, 2H), 4.57 (d, J=4.4 Hz, 1H), 3.76 (s, 3H), 3.50-3.34 (m, 1H), 3.02 (td, J=6.6, 4.0 Hz, 1H), 2.84-2.60 (m, 1H), 1.91 (d, J=9.9 Hz, 2H), 1.84-1.59 (m, 5H), 1.37-1.17 (m, 2H). MS (ESI) m/z: 434.2 [M+H+].

Provenance & Evidence