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

HRID 878200Notes

Reaction equation

HRID 878200 reaction equation
[CH3:1][O:2][C:3](=[O:21])[CH2:4][NH:5][C:6]1[CH:7]=[N:8][CH:9]=[CH:10][C:11]=1[C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:13]=1[O:19][CH3:20].[F:22][C:23]([F:38])([F:37])[C:24]1[CH:25]=[C:26]([CH:30]=[C:31]([C:33]([F:36])([F:35])[F:34])[N:32]=1)[C:27](O)=[O:28]>>[CH3:1][O:2][C:3](=[O:21])[CH2:4][N:5]([C:27]([C:26]1[CH:30]=[C:31]([C:33]([F:34])([F:35])[F:36])[N:32]=[C:24]([C:23]([F:38])([F:22])[F:37])[CH:25]=1)=[O:28])[C:6]1[CH:7]=[N:8][CH:9]=[CH:10][C:11]=1[C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:13]=1[O:19][CH3:20]

Participants

3

Reactant 2

HCID 306891352,6-Bis(trifluoromethyl)pyridine-4-carboxylic acidHCID 70663553[4-(4-Fluoro-2-methoxy-phenyl)-pyridin-3-ylamino]-acetic acid methyl ester

Product 1

HCID 86670784{(2,6-Bis-trifluoromethyl-pyridine-4-carbonyl)-[4-(4-fluoro-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-fluoro-2-methoxy-phenyl)-pyridin-3-ylamino]-acetic acid methyl ester 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 20:80). Colorless solid (46%). MS (ESI): m/z=532.109 [M+H]+.

Workup

  1. customThe compound was purified by silica gel chromatography
  2. washeluting with a gradient of n-heptane:EtOAc (100:0 to 20:80)

Sources & evidence

ORD record
ord-35513d9517934054b8bd99a07c5a1717
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

Loading…