2-Chloro-5-(trifluoromethyl)pyridine → 2,6-Difluoro-N-[(1S,2S)-2-{[5-(trifluoromethyl)pyridin-2-yl]amino}cyclopentyl]benzamide

HRID 1750639Notes

Reaction equation

HRID 1750639 reaction equation
ClC1C=CC=CC=1C(N[C@H]1CCC[C@@H]1N[C:13]1[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][N:14]=1)=O.Cl.[NH2:28][C@H:29]1[CH2:33][CH2:32][CH2:31][C@@H:30]1[NH:34][C:35](=[O:44])[C:36]1[C:41]([F:42])=[CH:40][CH:39]=[CH:38][C:37]=1[F:43].ClC1C=CC(C(F)(F)F)=CN=1>>[F:42][C:41]1[CH:40]=[CH:39][CH:38]=[C:37]([F:43])[C:36]=1[C:35]([NH:34][C@H:30]1[CH2:31][CH2:32][CH2:33][C@@H:29]1[NH:28][C:13]1[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][N:14]=1)=[O:44]

Participants

4

Reactant 3

HCID 923422-Chloro-5-(trifluoromethyl)pyridineHCID 118308046N-[(1S,2S)-2-Aminocyclopentyl]-2,6-difluorobenzamide hydrochloride2×HCID 1183081262-Chloro-N-[(1S,2S)-2-{[5-(trifluoromethyl)pyridin-2-yl]amino}cyclopentyl]benzamide

Product 1

HCID 1183081572,6-Difluoro-N-[(1S,2S)-2-{[5-(trifluoromethyl)pyridin-2-yl]amino}cyclopentyl]benzamide

Procedure

Prepared according to the procedure for 2-chloro-N-[(1S,2S)-2-{[5-(trifluoromethyl)pyridin-2-yl]amino}cyclopentyl]benzamide (Example 69) from N-[(1S,2S)-2-amino cyclopentyl]-2,6-difluorobenzamide hydrochloride (Intermediate 21; 100 mg, 0.36 mmol) and 2-chloro-5-(trifluoromethyl)pyridine (CAS number 52334-81-3; 79 mg, 0.43 mmol) to afford the title compound.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-30a5f67dec1b4cb9850120aef2a5de9d
Source dataset
uspto-grants-2015_10
Patent number
US09156829B2

Reaction notes

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