N-methyl-2-[1-[[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl]-4-piperidinyl]-N-[(1R,4S)-1,2,3,4-tetrahydro-4-hydroxy-1-naphthalenyl]-4-thiazolecarboxamide → N-methyl-2-[1-[[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl]-4-piperidinyl]-N-(1,2,3,4-tetrahydro-4-oxo-1-naphthalenyl)-4-thiazolecarboxamide

HRID 2043776Notes

Reaction equation

HRID 2043776 reaction equation
[CH3:1][N:2]([C@H:29]1[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[C@@H:32]([OH:39])[CH2:31][CH2:30]1)[C:3]([C:5]1[N:6]=[C:7]([CH:10]2[CH2:15][CH2:14][N:13]([C:16](=[O:28])[CH2:17][N:18]3[C:22]([CH3:23])=[CH:21][C:20]([C:24]([F:27])([F:26])[F:25])=[N:19]3)[CH2:12][CH2:11]2)[S:8][CH:9]=1)=[O:4]>C(Cl)(Cl)Cl.[O-2].[O-2].[Mn+4]>[CH3:1][N:2]([CH:29]1[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[C:32](=[O:39])[CH2:31][CH2:30]1)[C:3]([C:5]1[N:6]=[C:7]([CH:10]2[CH2:11][CH2:12][N:13]([C:16](=[O:28])[CH2:17][N:18]3[C:22]([CH3:23])=[CH:21][C:20]([C:24]([F:27])([F:26])[F:25])=[N:19]3)[CH2:14][CH2:15]2)[S:8][CH:9]=1)=[O:4]

Participants

4

Reactant 1

HCID 66796075N-methyl-2-[1-[[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl]-4-piperidinyl]-N-[(1R,4S)-1,2,3,4-tetrahydro-4-hydroxy-1-naphthalenyl]-4-thiazolecarboxamide2×

Product 1

HCID 66795730N-methyl-2-[1-[[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl]-4-piperidinyl]-N-(1,2,3,4-tetrahydro-4-oxo-1-naphthalenyl)-4-thiazolecarboxamide

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6212ChloroformSolvent

Procedure

A mixture of N-methyl-2-[1-[[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl]-4-piperidinyl]-N-[(1R,4S)-1,2,3,4-tetrahydro-4-hydroxy-1-naphthalenyl]-4-thiazolecarboxamide and its enantiomer (96 mg, 0.17 mmol) (i.e. the product of Example 26, Step B) and manganese dioxide (400 mg, 4.6 mmol) in chloroform (2 mL) were swirled to form a vortex overnight at room temperature. The reaction mixture was filtered through Celite® diatomaceous filter aid, and purified by medium-pressure liquid chromatography on silica gel using 20% acetone in ethyl acetate as eluant to give 70 mg of the title compound, a compound of the present invention as a white foam.

Workup

  1. customto form a vortex overnight at room temperature
  2. filtrationThe reaction mixture was filtered through Celite®
  3. filtrationdiatomaceous filter aid
  4. custompurified by medium-pressure liquid chromatography on silica gel using 20% acetone in ethyl acetate as eluant

Sources & evidence

ORD record
ord-36bfd517edae466ea781e95a164ab06e
Source dataset
uspto-grants-2013_11
Patent number
US08586611B2

Reaction notes

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