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

HRID 1504579Notes

Reaction equation

HRID 1504579 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-2b54896e1cb04e0b81efba96062fb6b1
Source dataset
uspto-grants-2015_12
Patent number
US09215875B2

Reaction notes

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