Methanol → methyl 4-[4-(4,5-dihydro-5-phenyl-3-isoxazoly)-2-thiazolyl]-N-(2,5-dimethylphenyl)-1-piperidinecarboximidate

HRID 1802321Notes

Reaction equation

HRID 1802321 reaction equation
[C:1]1([CH:7]2[O:11][N:10]=[C:9]([C:12]3[N:13]=[C:14]([CH:17]4[CH2:22][CH2:21][N:20]([C:23](SC)=[N:24][C:25]5[CH:30]=[C:29]([CH3:31])[CH:28]=[CH:27][C:26]=5[CH3:32])[CH2:19][CH2:18]4)[S:15][CH:16]=3)[CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:35][OH:36]>>[C:1]1([CH:7]2[O:11][N:10]=[C:9]([C:12]3[N:13]=[C:14]([CH:17]4[CH2:22][CH2:21][N:20]([C:23](=[N:24][C:25]5[CH:30]=[C:29]([CH3:31])[CH:28]=[CH:27][C:26]=5[CH3:32])[O:36][CH3:35])[CH2:19][CH2:18]4)[S:15][CH:16]=3)[CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 2

HCID 887MethanolHCID 66633932methyl 4-[4-(4,5-dihydro-5-phenyl-3-isoxazolyl)-2-thiazolyl]-N-(2,5-dimethylphenyl)-1-piperidinecarboximidothioate

Product 1

HCID 66633372methyl 4-[4-(4,5-dihydro-5-phenyl-3-isoxazoly)-2-thiazolyl]-N-(2,5-dimethylphenyl)-1-piperidinecarboximidate

Procedure

A solution of methyl 4-[4-(4,5-dihydro-5-phenyl-3-isoxazolyl)-2-thiazolyl]-N-(2,5-dimethylphenyl)-1-piperidinecarboximidothioate (i.e. the product of Example 1, Step D) (0.10 g, 0.20 mmol) in methanol (5 mL) was heated in a Biotage® Creator XM microwave apparatus at 140° C. for 1.5 h. The reaction mixture was concentrated under reduced pressure. The resulting residue was purified by column chromatography on silica gel using 1:1 ethyl acetate-hexanes as eluant to provide the title compound, a compound of the present invention, as a foamy white solid (19 mg).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customThe resulting residue was purified by column chromatography on silica gel using 1:1 ethyl acetate-hexanes as eluant

Sources & evidence

ORD record
ord-33dd86805d2c4bf4bb4e51f84a0d2bb8
Source dataset
uspto-grants-2013_01
Patent number
US08349870B2

Reaction notes

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