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

HRID 1750638Notes

Reaction equation

HRID 1750638 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:45])[C:36]1[C:41]([O:42][CH3:43])=[CH:40][CH:39]=[CH:38][C:37]=1[F:44].ClC1C=CC(C(F)(F)F)=CN=1>>[F:44][C:37]1[CH:38]=[CH:39][CH:40]=[C:41]([O:42][CH3:43])[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:45]

Participants

4

Reactant 3

HCID 923422-Chloro-5-(trifluoromethyl)pyridineHCID 1183081262-Chloro-N-[(1S,2S)-2-{[5-(trifluoromethyl)pyridin-2-yl]amino}cyclopentyl]benzamideHCID 118308173N-[(1S,2S)-2-Aminocyclopentyl]-2-fluoro-6-methoxybenzamide hydrochloride2×

Product 1

HCID 1183083002-Fluoro-6-methoxy-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-aminocyclopentyl]-2-fluoro-6-methoxybenzamide hydrochloride (Intermediate 20; 50 mg, 0.17 mmol) and 2-chloro-5-(trifluoromethyl)pyridine (CAS number 52334-81-3; 38 mg, 0.21 mmol) to afford the title compound.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-177b4159ebb0483abebb88b080ac9b0e
Source dataset
uspto-grants-2015_10
Patent number
US09156829B2

Reaction notes

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