2,6-Bis(trifluoromethyl)pyridine-4-carboxylic acid → {(2,6-Bis-trifluoromethyl-pyridine-4-carbonyl)-[4-(4,5-difluoro-2-methoxy-phenyl)-pyridin-3-yl]-amino}-acetic acid methyl ester

HRID 878197Notes

Reaction equation

HRID 878197 reaction equation
[CH3:1][O:2][C:3](=[O:22])[CH2:4][NH:5][C:6]1[CH:7]=[N:8][CH:9]=[CH:10][C:11]=1[C:12]1[CH:17]=[C:16]([F:18])[C:15]([F:19])=[CH:14][C:13]=1[O:20][CH3:21].[F:23][C:24]([F:39])([F:38])[C:25]1[CH:26]=[C:27]([CH:31]=[C:32]([C:34]([F:37])([F:36])[F:35])[N:33]=1)[C:28](O)=[O:29]>>[CH3:1][O:2][C:3](=[O:22])[CH2:4][N:5]([C:28]([C:27]1[CH:31]=[C:32]([C:34]([F:35])([F:36])[F:37])[N:33]=[C:25]([C:24]([F:39])([F:23])[F:38])[CH:26]=1)=[O:29])[C:6]1[CH:7]=[N:8][CH:9]=[CH:10][C:11]=1[C:12]1[CH:17]=[C:16]([F:18])[C:15]([F:19])=[CH:14][C:13]=1[O:20][CH3:21]

Participants

3

Reactant 2

HCID 306891352,6-Bis(trifluoromethyl)pyridine-4-carboxylic acidHCID 70663491[4-(4,5-Difluoro-2-methoxy-phenyl)-pyridin-3-ylamino]-acetic acid methyl ester

Product 1

HCID 86670782{(2,6-Bis-trifluoromethyl-pyridine-4-carbonyl)-[4-(4,5-difluoro-2-methoxy-phenyl)-pyridin-3-yl]-amino}-acetic acid methyl ester

Procedure

The title compound was prepared in analogy to example 90, from [4-(4,5-difluoro-2-methoxy-phenyl)-pyridin-3-ylamino]-acetic acid methyl ester (example 172, intermediate a) and 2,6-bis(trifluoromethyl)isonicotinic acid (Key Organics Ltd.) after a reaction time of 72 hours. The compound was purified by silica gel chromatography using a MPLC system (CombiFlash Companion, Isco Inc.) eluting with a gradient of n-heptane:EtOAc (100:0 to 0:80). Colorless solid (48%). MS (ESI): m/z=550.102 [M+H]+.

Workup

  1. customThe compound was purified by silica gel chromatography
  2. washeluting with a gradient of n-heptane:EtOAc (100:0 to 0:80)

Sources & evidence

ORD record
ord-726e3fd9356b4f4abf3ae7b94e3a603a
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

Loading…