4-(3-Methanesulfonyloxymethyl-[1,2,4]triazol-1-yl)-piperidine-1-carboxylic acid tert-butyl ester → ethyl 1-(1-(5-ethylpyrimidin-2-yl)piperidin-4-yl)-3-(trifluoromethyl)-1H-pyrazole-4-carboxylate
Reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][NH:5][N:4]=1.CS(O[CH:20]1[CH2:25][CH2:24][N:23]([C:26]2[N:31]=[CH:30][C:29]([CH2:32][CH3:33])=[CH:28][N:27]=2)[CH2:22][CH2:21]1)(=O)=O.C(OC(N1CCC(N2C=NC(COS(C)(=O)=O)=N2)CC1)=O)(C)(C)C>>[CH2:32]([C:29]1[CH:28]=[N:27][C:26]([N:23]2[CH2:24][CH2:25][CH:20]([N:5]3[CH:6]=[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:3]([C:2]([F:1])([F:13])[F:14])=[N:4]3)[CH2:21][CH2:22]2)=[N:31][CH:30]=1)[CH3:33].[CH2:32]([C:29]1[CH:28]=[N:27][C:26]([N:23]2[CH2:24][CH2:25][CH:20]([N:4]3[C:3]([C:2]([F:1])([F:13])[F:14])=[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH:6]=[N:5]3)[CH2:21][CH2:22]2)=[N:31][CH:30]=1)[CH3:33]Participants
5
Reactant 3
Product 2
Procedure
The compound was synthesized using ethyl 3-(trifluoromethyl)-1H-pyrazole-4-carboxylate and 1-(5-ethylpyrimidin-2-yl)piperidin-4-yl methanesulfonate in a manner similar to that described in Intermediate 1, Step 1. The reaction afforded two regioisomers, ethyl 1-(1-(5-ethylpyrimidin-2-yl)piperidin-4-yl)-3-(trifluoromethyl)-1H-pyrazole-4-carboxylate and ethyl 1-(1-(5-ethylpyrimidin-2-yl)piperidin-4-yl)-5-(trifluoromethyl)-1H-pyrazole-4-carboxylate which were separated by flash column chromatography on silica gel.
Workup
- customThe compound was synthesized
Sources & evidence
- ORD record
- ord-dac830a4e18d45fe8b89dc7e1828c1af
- Source dataset
- uspto-grants-2012_05
- Patent number
- US08183381B2
Reaction notes
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