2-Chloro-3-methoxybenzoic acid → 2-chloro-3-methoxy-N-(3-cyclopropyl-2-(6-(difluoromethyl)pyridin-3-yl)propyl)benzamide

HRID 512429Notes

Reaction equation

HRID 512429 reaction equation
[Cl:1][C:2]1[C:10]([O:11][CH3:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.[CH:13]1([CH2:16][CH:17]([C:20]2[CH:21]=[N:22][C:23]([CH:26]([F:28])[F:27])=[CH:24][CH:25]=2)[CH2:18][NH2:19])[CH2:15][CH2:14]1>>[Cl:1][C:2]1[C:10]([O:11][CH3:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([NH:19][CH2:18][CH:17]([C:20]1[CH:21]=[N:22][C:23]([CH:26]([F:28])[F:27])=[CH:24][CH:25]=1)[CH2:16][CH:13]1[CH2:14][CH2:15]1)=[O:6]

Participants

3

Reactant 2

HCID 162180632-Chloro-3-methoxybenzoic acidHCID 867164003-Cyclopropyl-2-(6-(difluoromethyl)pyridin-3-yl)propan-1-amine

Product 1

HCID 867164032-chloro-3-methoxy-N-(3-cyclopropyl-2-(6-(difluoromethyl)pyridin-3-yl)propyl)benzamide

Procedure

The racemic mixture which was prepared in a similar manner to example 3a from 2-chloro-3-methoxybenzoic acid and 3-cyclopropyl-2-(6-(difluoromethyl)pyridin-3-yl)propan-1-amine was separated into the two enantiomers by preparative SFC to yield the title compound. LCMS (MH+): m/z=395.1, tR (minutes, Method F)=2.96. [α]D20=+28.21 (c=2.80 mg/mL,CHCl3)

Workup

  1. customwas separated into the two enantiomers by preparative SFC

Sources & evidence

ORD record
ord-0b35b725563d47e7b8048457475dd509
Source dataset
uspto-grants-2015_08
Patent number
US09102591B2

Reaction notes

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