3-Amino-6-(2,4-dichloro-phenyl)-5-trifluoromethyl-pyridine-2-carboxylic acid → US10117858, Example 9

HRID 444904Notes

Reaction equation

HRID 444904 reaction equation
[NH2:1][C:2]1[C:3]([C:20](O)=[O:21])=[N:4][C:5]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:13]=2[Cl:19])=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.Cl.[NH2:24][CH2:25][C:26]([CH3:32])([OH:31])[C:27]([F:30])([F:29])[F:28]>>[F:28][C:27]([F:30])([F:29])[C:26]([OH:31])([CH3:32])[CH2:25][NH:24][C:20]([C:3]1[C:2]([NH2:1])=[CH:7][C:6]([C:8]([F:10])([F:9])[F:11])=[C:5]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:13]=2[Cl:19])[N:4]=1)=[O:21]

Participants

3

Reactant 2

HCID 584423403-Amino-6-(2,4-dichloro-phenyl)-5-trifluoromethyl-pyridine-2-carboxylic acid2×HCID 717573513-Amino-1,1,1-trifluoro-2-methylpropan-2-ol hydrochloride

Product 1

HCID 58442319US10117858, Example 9

Procedure

The enantiomers of 3-amino-6-(2,4-dichloro-phenyl)-5-trifluoromethyl-pyridine-2-carboxylic acid (3,3,3-trifluoro-2-hydroxy-2-methyl-propyl)-amide were prepared from 3-Amino-6-(2,4-dichloro-phenyl)-5-trifluoromethyl-pyridine-2-carboxylic acid (Intermediate H) and 3-amino-1,1,1-trifluoro-2-methylpropan-2-ol hydrochloride analogously to Example 1 and separated by chiral separation using Supercritical Fluid Chromatography:

Workup

  1. customseparated by chiral separation

Sources & evidence

ORD record
ord-5c96f995b0fd4e95b6f972df803fda5c
Source dataset
uspto-grants-2013_07
Patent number
US08476269B2

Reaction notes

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