2-Chloro-3-fluorobenzoic acid → HCID 86716368, compound

HRID 512406Notes

Reaction equation

HRID 512406 reaction equation
[Cl:1][C:2]1[C:10]([F:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.[F:12][C:13]([F:32])([F:31])[C:14]1([CH2:17][CH:18]([C:21]2[CH:22]=[N:23][C:24]([C:27]([F:30])([F:29])[F:28])=[N:25][CH:26]=2)[CH2:19][NH2:20])[CH2:16][CH2:15]1>>[Cl:1][C:2]1[C:10]([F:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([NH:20][CH2:19][CH:18]([C:21]1[CH:22]=[N:23][C:24]([C:27]([F:30])([F:29])[F:28])=[N:25][CH:26]=1)[CH2:17][C:14]1([C:13]([F:12])([F:31])[F:32])[CH2:16][CH2:15]1)=[O:6]

Participants

3

Reactant 2

HCID 3026202-Chloro-3-fluorobenzoic acidHCID 86716367HCID 86716367, compound

Product 1

HCID 86716368HCID 86716368, compound

Procedure

The racemic mixture which was prepared in a similar manner to example 3a from 2-chloro-3-fluorobenzoic acid and 3-(1-(trifluoromethyl)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=470.0, tR (minutes, Method F)=3.07. [α]D20=28.85 (c=3.05 mg/mL,CHCl3)

Workup

  1. customwas separated into the two enantiomers by preparative SFC

Sources & evidence

ORD record
ord-c6697f5b62f345088c54e8e18e21d72e
Source dataset
uspto-grants-2015_08
Patent number
US09102591B2

Reaction notes

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