2-(1-Methylhydrazinyl)-5-(trifluoromethyl)pyridine → HCID 86643690, compound
Reaction equation
[CH3:1][N:2]([C:4]1[CH:9]=[CH:8][C:7]([C:10]([F:13])([F:12])[F:11])=[CH:6][N:5]=1)[NH2:3].[CH3:14][C:15]1[N:19]([CH2:20][C:21]([N:23]2[CH2:28][CH2:27][CH:26]([C:29]3[S:30][CH:31]=[C:32]([CH:34]=O)[N:33]=3)[CH2:25][CH2:24]2)=[O:22])[N:18]=[C:17]([C:36]([F:39])([F:38])[F:37])[CH:16]=1>C(O)C>[CH3:1][N:2]([C:4]1[CH:9]=[CH:8][C:7]([C:10]([F:13])([F:11])[F:12])=[CH:6][N:5]=1)[N:3]=[CH:34][C:32]1[N:33]=[C:29]([CH:26]2[CH2:25][CH2:24][N:23]([C:21](=[O:22])[CH2:20][N:19]3[C:15]([CH3:14])=[CH:16][C:17]([C:36]([F:37])([F:39])[F:38])=[N:18]3)[CH2:28][CH2:27]2)[S:30][CH:31]=1Participants
4
Procedure
At room temperature, 2-(1-methylhydrazinyl)-5-(trifluoromethyl)pyridine (58 mg) is added to a solution of 2-(1-{[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazole-4-carbaldehyde (100 mg) in ethanol. The reaction mixture is stirred for 24 hours, and the solvent is then removed under reduced pressure. The residue is purified by column chromatography (silica gel, ethyl acetate:hexane 0%-100% elution gradient). This gives 2-(1-{[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazole-4-carbaldehyde methyl[5-(trifluoromethyl)pyridin-2-yl]hydrazone (79 mg, 56%), (log P(pH2.7)=4.23).