3-ethyl-4-methyl-1H-pyrazol-5-amine → HCID 178437903, compound

Reaction equation

[Cl:1][C:2]1[CH:3]=[N:4][C:5]([CH3:19])=[C:6]([CH:18]=1)[C:7]([NH:9][C@H:10]1[CH2:15][CH2:14][C@H:13]([CH:16]=O)[CH2:12][CH2:11]1)=[O:8].[CH2:20]([C:22]1[NH:26][N:25]=[C:24]([NH2:27])[C:23]=1[CH3:28])[CH3:21].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[N:4][C:5]([CH3:19])=[C:6]([CH:18]=1)[C:7]([NH:9][C@H:10]1[CH2:15][CH2:14][C@H:13]([CH2:16][NH:27][C:24]2[C:23]([CH3:28])=[C:22]([CH2:20][CH3:21])[NH:26][N:25]=2)[CH2:12][CH2:11]1)=[O:8]

Participants

Procedure

A mixture comprising trans-5-chloro-N-(4-formyl-cyclohexyl)-2-methyl-nicotinamide Intermediate E) (100 mg, 0.30 mmol) and 5-ethyl-4-methyl-1H-pyrazol-3-amine (37.5 mg, 0.30 mmol) in DCM (5 ml) was treated with sodium triacetoxyborohydride (95 mg, 0.45 mmol). The reaction mixture was stirred at RT for 18 hours and then partitioned between DCM and sat. NaHCO3. The organic phase was passed through a phase separator and the solvent was removed in vacuo. The resulting crude product was triturated in EtOAc, filtered and dried to afford the title compound; 1H NMR (d6-DMSO, 400 MHz) δ 10.87 (1H, s), 8.53 (1H, m), 8.40 (1H, m), 7.80 (1H, m), 4.43 (1H, m), 3.69 (1H, m), 2.90 (2H, t), 2.50 (3H, s), 2.40 (2H, q), 1.88 (4H, m), 1.73 (3H, s), 1.53 (1H, m), 1.21 (2H, m), 1.09 (3H, t), 1.00 (2H, m); LCMS Rt=2.06 min, [M+H]+390 Method LowpH_v002.