3,5-Bis(trifluoromethyl)benzoic acid → N-[4-(2-Cyanomethyl-phenyl)-pyridin-3-yl]-N-methyl-3,5-bis-trifluoromethyl-benzamide

HRID 878198Notes

Reaction equation

HRID 878198 reaction equation
[CH3:1][NH:2][C:3]1[CH:4]=[N:5][CH:6]=[CH:7][C:8]=1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH2:15][C:16]#[N:17].[F:18][C:19]([F:34])([F:33])[C:20]1[CH:21]=[C:22]([CH:26]=[C:27]([C:29]([F:32])([F:31])[F:30])[CH:28]=1)[C:23]([OH:25])=O>>[C:16]([CH2:15][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[C:8]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[N:2]([CH3:1])[C:23](=[O:25])[C:22]1[CH:26]=[C:27]([C:29]([F:32])([F:31])[F:30])[CH:28]=[C:20]([C:19]([F:18])([F:34])[F:33])[CH:21]=1)#[N:17]

Participants

3

Reactant 2

HCID 128893,5-Bis(trifluoromethyl)benzoic acidHCID 70663360[2-(3-Methylamino-pyridin-4-yl)-phenyl]-acetonitrile

Product 1

HCID 86670783N-[4-(2-Cyanomethyl-phenyl)-pyridin-3-yl]-N-methyl-3,5-bis-trifluoromethyl-benzamide

Procedure

The title compound was prepared in analogy to example 90, from [2-(3-methylamino-pyridin-4-yl)-phenyl]-acetonitrile and 3,5-bis(trifluoromethyl)benzoic acid (CAS RN 725-89-3) after a reaction time of 5 days. 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 50:50) followed by a second chromatography, using preparative HPLC (Phenomenex Gemini® column, gradient of methanol:water (10:90 to 95:5)). Colorless solid (3%). MS (ESI): m/z=464.118 [M+H]+.

Workup

  1. customThe compound was purified by silica gel chromatography
  2. washeluting with a gradient of n-heptane:EtOAc (100:0 to 50:50)

Sources & evidence

ORD record
ord-8ec0e1b7de7046d0ab569d598a2038c4
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

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