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

HRID 1750667Notes

Reaction equation

HRID 1750667 reaction equation
ClC1C=CC(N2N=CC=N2)=C(C=1)[C:7]([NH:9][C@H:10]1[CH2:14][CH2:13][CH2:12][C@@H:11]1[NH:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][N:17]=1)=[O:8].Cl.FC(F)(F)C1C=CC(N[C@H]2CCC[C@@H]2N)=NC=1.[N:50]1([C:55]2[C:56](C(O)=O)=[N:57][CH:58]=[CH:59][CH:60]=2)[CH:54]=[CH:53][CH:52]=[N:51]1>>[N:50]1([C:55]2[C:56]([C:7]([NH:9][C@H:10]3[CH2:14][CH2:13][CH2:12][C@@H:11]3[NH:15][C:16]3[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:23])[F:24])=[CH:18][N:17]=3)=[O:8])=[N:57][CH:58]=[CH:59][CH:60]=2)[CH:54]=[CH:53][CH:52]=[N:51]1

Participants

4

Reactant 3

HCID 730111773-(1H-pyrazol-1-yl)pyridine-2-carboxylic acidHCID 1183080695-Chloro-2-(2H-1,2,3-triazol-2-yl)-N-[(1S,2S)-2-{[5-(trifluoromethyl)pyridin-2-yl]amino}cyclopentyl]benzamideHCID 118308256(1S,2S)-1-N-[5-(Trifluoromethyl)pyridin-2-yl]cyclopentane-1,2-diamine hydrochloride2×

Product 1

HCID 1183080523-(1H-Pyrazol-1-yl)-N-[(1S,2S)-2-{[5-(trifluoromethyl)pyridin-2-yl]amino}cyclopentyl]pyridine-2-carboxamide

Procedure

Prepared according to the procedure for 5-chloro-2-(2H-1,2,3-triazol-2-yl)-N-[(1S,2S)-2-{[5-(trifluoromethyl)pyridin-2-yl]amino}cyclopentyl]benzamide (Example 97) from (1S,2S)-1-N-[5-(trifluoromethyl)pyridin-2-yl]cyclopentane-1,2-diamine hydrochloride (Intermediate 1; 50 mg, 0.20 mmol) and 3-(1H-pyrazol-1-yl)pyridine-2-carboxylic acid (CAS number 1521232-19-8; 38 mg, 0.20 mmol) to afford the title compound.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-fc46cb9c1af34d5eb2705a1c0fd2ed49
Source dataset
uspto-grants-2015_10
Patent number
US09156829B2

Reaction notes

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