2-Chloro-6-fluorobenzoic acid → 2-chloro-N-(3-cyclopropyl-2-(6-(trifluoromethyl)pyridin-3-yl)propyl)-6-fluorobenzamide

HRID 512392Notes

Reaction equation

HRID 512392 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([F:11])[C:3]=1[C:4]([OH:6])=O.[CH:12]1([CH2:15][CH:16]([C:19]2[CH:20]=[N:21][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:23][CH:24]=2)[CH2:17][NH2:18])[CH2:14][CH2:13]1>>[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([F:11])[C:3]=1[C:4]([NH:18][CH2:17][CH:16]([C:19]1[CH:20]=[N:21][C:22]([C:25]([F:28])([F:26])[F:27])=[CH:23][CH:24]=1)[CH2:15][CH:12]1[CH2:13][CH2:14]1)=[O:6]

Participants

3

Reactant 2

HCID 679472-Chloro-6-fluorobenzoic acidHCID 867162843-Cyclopropyl-2-(6-trifluoromethyl-pyridin-3-yl)-propylamine

Product 1

HCID 867163192-chloro-N-(3-cyclopropyl-2-(6-(trifluoromethyl)pyridin-3-yl)propyl)-6-fluorobenzamide

Procedure

The racemic mixture which was prepared in a similar manner to example 3a from 2-chloro-6-fluorobenzoic acid and 3-cyclopropyl-2-(6-(trifluoromethyl)pyridin-3-yl)propan-1-amine was separated into the two enantiomers by preparative SFC to yield the title compound. LCMS (MH+): m/z=401.1, tR (minutes, Method G)=2.88. [α]D20=−25.9 (c=0.81 mg/mL,CHCl3)

Workup

  1. customwas separated into the two enantiomers by preparative SFC

Sources & evidence

ORD record
ord-d56e67700e9a430e9f6b93b9fba41179
Source dataset
uspto-grants-2015_08
Patent number
US09102591B2

Reaction notes

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