2-(1-Methylhydrazinyl)-5-(trifluoromethyl)pyridine → HCID 86643690, compound

HRID 2367072Notes

Reaction equation

HRID 2367072 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]=1

Participants

4

Reactant 2

HCID 27777822-(1-Methylhydrazinyl)-5-(trifluoromethyl)pyridineHCID 86631244HCID 86631244, compound

Product 1

HCID 86643690HCID 86643690, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

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).

Workup

  1. customthe solvent is then removed under reduced pressure
  2. customThe residue is purified by column chromatography (silica gel, ethyl acetate:hexane 0%-100% elution gradient)

Sources & evidence

ORD record
ord-346aea4c00924b5385a6f28022f45f51
Source dataset
uspto-grants-2014_04
Patent number
US08697878B2

Reaction notes

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