3-Methanesulfonyl-5-(trifluoromethyl)benzoic acid → 3-Methanesulfonyl-N-(2-methoxy-[3,4']bipyridinyl-3'-yl)-N-(2,2,2-trifluoro-ethyl)-5-trifluoromethyl-benzamide

HRID 878148Notes

Reaction equation

HRID 878148 reaction equation
[CH3:1][O:2][C:3]1[C:8]([C:9]2[CH:14]=[CH:13][N:12]=[CH:11][C:10]=2[NH:15][CH2:16][C:17]([F:20])([F:19])[F:18])=[CH:7][CH:6]=[CH:5][N:4]=1.[CH3:21][S:22]([C:25]1[CH:26]=[C:27]([CH:31]=[C:32]([C:34]([F:37])([F:36])[F:35])[CH:33]=1)[C:28](O)=[O:29])(=[O:24])=[O:23]>>[CH3:21][S:22]([C:25]1[CH:26]=[C:27]([CH:31]=[C:32]([C:34]([F:35])([F:36])[F:37])[CH:33]=1)[C:28]([N:15]([C:10]1[CH:11]=[N:12][CH:13]=[CH:14][C:9]=1[C:8]1[C:3]([O:2][CH3:1])=[N:4][CH:5]=[CH:6][CH:7]=1)[CH2:16][C:17]([F:18])([F:20])[F:19])=[O:29])(=[O:24])=[O:23]

Participants

3

Reactant 2

HCID 215445163-Methanesulfonyl-5-(trifluoromethyl)benzoic acidHCID 70663300(2-Methoxy-[3,4]bipyridinyl-3'-yl)-(2,2,2-trifluoro-ethyl)-amine

Product 1

HCID 601980263-Methanesulfonyl-N-(2-methoxy-[3,4']bipyridinyl-3'-yl)-N-(2,2,2-trifluoro-ethyl)-5-trifluoromethyl-benzamide

Procedure

The title compound was prepared in analogy to example 90, from (2-methoxy-[3,4′]bipyridinyl-3′-yl)-(2,2,2-trifluoro-ethyl)-amine (example 135, intermediate a) and 3-methanesulfonyl-5-trifluoromethyl-benzoic acid (example 114, intermediate a) 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 CH2Cl2: EtOAc (100:0 to 85:15), followed by preparative HPLC using a gradient of methanol:water (10:50 to 95:5). Light yellow foam (28%). MS (ESI): m/z=534.090 [M+H]+.

Workup

  1. customThe compound was purified by silica gel chromatography
  2. washeluting with a gradient of CH2Cl2: EtOAc (100:0 to 85:15)

Sources & evidence

ORD record
ord-3bc0271955844dbca354d5a5e7a0d683
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

Loading…