2-Chloro-3-methoxybenzoic acid → 2-chloro-N-(3-cyclopropyl-2-(2-(trifluoromethyl)pyrimidin-5-yl)propyl)-3-methoxybenzamide

HRID 512396Notes

Reaction equation

HRID 512396 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]([C:26]([F:29])([F:28])[F:27])=[N: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]([C:26]([F:29])([F:28])[F:27])=[N:24][CH:25]=1)[CH2:16][CH:13]1[CH2:15][CH2:14]1)=[O:6]

Participants

3

Reactant 2

HCID 162180632-Chloro-3-methoxybenzoic acidHCID 867163152-(2-Trifluoromethyl-pyrimidin-5-yl)-3-cyclopropyl-propylamine

Product 1

HCID 867163422-chloro-N-(3-cyclopropyl-2-(2-(trifluoromethyl)pyrimidin-5-yl)propyl)-3-methoxybenzamide

Procedure

The racemic mixture which was prepared in a similar manner to example 3a from 2-chloro-3-methoxybenzoic acid and 3-cyclopropyl-2-(2-(trifluoromethyl)pyrimidin-5-yl)propan-1-amine was separated into the two enantiomers by preparative SFC to yield the title compound. LCMS (MH+): m/z=414.0, tR (minutes, Method F)=2.53. [α]D20=+26.3 (c=4.0 mg/mL,CHCl3)

Workup

  1. customwas separated into the two enantiomers by preparative SFC

Sources & evidence

ORD record
ord-8b9e2e95236a44aa9d1701b0e3a6cfe9
Source dataset
uspto-grants-2015_08
Patent number
US09102591B2

Reaction notes

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