3-(1H-pyrazol-1-yl)pyridine-2-carboxylic acid → N-[(1S,2S)-2-Methyl-2-{[5-(trifluoromethyl)pyrazin-2-yl]amino}cyclopentyl]-3-(1H-pyrazol-1-yl)pyridine-2-carboxamide

HRID 1750652Notes

Reaction equation

HRID 1750652 reaction equation
[CH3:1][C@:2]1([NH:21][C:22]2[CH:27]=[N:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][N:23]=2)[CH2:6][CH2:5][CH2:4][C@@H:3]1[NH:7][C:8]([C:10]1[C:15]([N:16]2N=[CH:19][CH:18]=[N:17]2)=[CH:14][CH:13]=[CH:12][N:11]=1)=[O:9].[CH3:32][C@]1(NC2C=NC(C(F)(F)F)=CN=2)CCC[C@@H]1N.N1(C2C(C(O)=O)=NC=CC=2)C=CC=N1>>[CH3:1][C@:2]1([NH:21][C:22]2[CH:27]=[N:26][C:25]([C:28]([F:29])([F:30])[F:31])=[CH:24][N:23]=2)[CH2:6][CH2:5][CH2:4][C@@H:3]1[NH:7][C:8]([C:10]1[C:15]([N:16]2[CH:32]=[CH:19][CH:18]=[N:17]2)=[CH:14][CH:13]=[CH:12][N:11]=1)=[O:9]

Participants

4

Reactant 3

HCID 730111773-(1H-pyrazol-1-yl)pyridine-2-carboxylic acidHCID 118308048(1S,2S)-1-Methyl-1-N-[5-(trifluoromethyl)pyrazin-2-yl]cyclopentane-1,2-diamine2×HCID 118308152N-[(1S,2S)-2-Methyl-2-{[5-(trifluoromethyl)pyrazin-2-yl]amino}cyclopentyl]-3-(2H-1,2,3-triazol-2-yl)pyridine-2-carboxamide

Product 1

HCID 118308272N-[(1S,2S)-2-Methyl-2-{[5-(trifluoromethyl)pyrazin-2-yl]amino}cyclopentyl]-3-(1H-pyrazol-1-yl)pyridine-2-carboxamide

Procedure

Prepared according to the procedure for N-[(1S,2S)-2-methyl-2-{[5-(trifluoromethyl)pyrazin-2-yl]amino}cyclopentyl]-3-(2H-1,2,3-triazol-2-yl)pyridine-2-carboxamide (Example 77) from (1S,2S)-1-methyl-1-N-[5-(trifluoromethyl)pyrazin-2-yl]cyclopentane-1,2-diamine (Intermediate 25; 80 mg, 0.31 mmol) and 3-(1H-pyrazol-1-yl)pyridine-2-carboxylic acid (CAS number 1521232-19-8; 70 mg, 0.37 mmol) except this was purified by column chromatography (silica, 50-100% ethyl acetate/petrol then 0-10% methanol/ethyl acetate) followed by reverse phase chromatography (C18 silica, 0-100% water (with 0.05% ammonia)/acetonitrile) to afford the title compound.

Workup

  1. customPrepared
  2. customthis was purified by column chromatography (silica, 50-100% ethyl acetate/petrol

Sources & evidence

ORD record
ord-8834e94a7000440cae5d6170f1c6483b
Source dataset
uspto-grants-2015_10
Patent number
US09156829B2

Reaction notes

Loading…