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

HRID 878147Notes

Reaction equation

HRID 878147 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.[F:21][C:22]1[CH:23]=[C:24]([CH:28]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:30]=1)[C:25](O)=[O:26]>CCCCCCC.CCOC(C)=O>[F:21][C:22]1[CH:23]=[C:24]([CH:28]=[C:29]([C:31]([F:32])([F:33])[F:34])[CH:30]=1)[C:25]([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:26]

Participants

4

Reactant 2

HCID 5192223-Fluoro-5-(trifluoromethyl)benzoic acidHCID 70663300(2-Methoxy-[3,4]bipyridinyl-3'-yl)-(2,2,2-trifluoro-ethyl)-amine

Product 1

HCID 866707553-Fluoro-N-(2-methoxy-[3,4']bipyridinyl-3'-yl)-N-(2,2,2-trifluoro-ethyl)-5-trifluoromethyl-benzamide

Reagents, catalysts & solvents 1

HCID 21899848Ethylacetate heptaneSolvent

Procedure

The title compound was prepared in analogy to example 72, intermediate, from (2-methoxy-[3,4]bipyridinyl-3′-yl)-(2,2,2-trifluoro-ethyl)-amine (example 135, intermediate a) and 3-fluoro-5-(trifluoromethyl)benzoic acid (CAS RN 161622-05-5) and using a gradient of n-heptane:EtOAc (100:0 to 50:50) for the chromatographic purification. Light yellow solid (16%). MS (ESI): m/z=474.104 [M+H]+.

Workup

  1. customfor the chromatographic purification

Sources & evidence

ORD record
ord-a2b42a24862b4deeaca941838ecb032c
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

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