HCID 67424631, compound → HCID 86643689, compound

HRID 2367071Notes

Reaction equation

HRID 2367071 reaction equation
[Cl-].[C:2]1([CH:8]([O:10][NH3+:11])[CH3:9])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:12]([C:15]1[N:16]=[C:17]([CH:20]2[CH2:25][CH2:24][N:23]([C:26](=[O:38])[CH2:27][N:28]3[C:32]([CH3:33])=[CH:31][C:30]([C:34]([F:37])([F:36])[F:35])=[N:29]3)[CH2:22][CH2:21]2)[S:18][CH:19]=1)(=O)[CH3:13]>C(O)C>[CH3:33][C:32]1[N:28]([CH2:27][C:26]([N:23]2[CH2:24][CH2:25][CH:20]([C:17]3[S:18][CH:19]=[C:15]([C:12](=[N:11][O:10][CH:8]([C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)[CH3:9])[CH3:13])[N:16]=3)[CH2:21][CH2:22]2)=[O:38])[N:29]=[C:30]([C:34]([F:37])([F:36])[F:35])[CH:31]=1

Participants

4

Reactant 2

HCID 67424631HCID 67424631, compoundHCID 67433897HCID 67433897, compound

Product 1

HCID 86643689HCID 86643689, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

At room temperature, (1-phenylethoxy)ammonium chloride (91 mg) and Amberlyst A21 (300 mg) are added to a solution of 1-[4-(4-acetyl-1,3-thiazol-2-yl)piperidin-1-yl]-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone (200 mg) in ethanol. The reaction mixture is stirred for 24 hours, and the solvent is then removed under reduced pressure. The residue is separated by column chromatography (silica gel, ethyl acetate:hexane 0%-100% elution gradient). This gives 2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]-1-(4-{4-[N-(1-phenylethoxy)ethanimidoyl]-1,3-thiazol-2-yl}piperidin-1-yl)ethanone (230 mg, 89%) which consists of an about 9:1 mixture of trans and cis isomers (log P(pH2.7)=4.38 (89%), 4.54 (11%).

Workup

  1. customthe solvent is then removed under reduced pressure
  2. customThe residue is separated by column chromatography (silica gel, ethyl acetate:hexane 0%-100% elution gradient)
  3. additionabout 9:1 mixture of trans and cis isomers (log P(pH2.7)=4.38 (89%), 4.54 (11%)

Sources & evidence

ORD record
ord-5c348c910e7743a29661b13b61294759
Source dataset
uspto-grants-2014_04
Patent number
US08697878B2

Reaction notes

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