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

HRID 75499Notes

Reaction equation

HRID 75499 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

5

Reactant 3

HCID 31349413-ethyl-4-methyl-1H-pyrazol-5-amineHCID 5049666Sodium triacetoxyborohydrideHCID 178432774HCID 178432774, compound

Product 1

HCID 178437903HCID 178437903, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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.

Workup

  1. custompartitioned between DCM and sat. NaHCO3
  2. customthe solvent was removed in vacuo
  3. customThe resulting crude product was triturated in EtOAc
  4. filtrationfiltered
  5. customdried

Sources & evidence

ORD record
ord-34cf35e4dbf04b429917dc488efcea35
Source dataset
uspto-grants-2014_09
Patent number
US08835444B2

Reaction notes

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