Ammonium Hydroxide → 4-Methyl-2-[2-(5-methyl-3-phenyl-isoxazol-4-yl)-ethyl]thiazole-5-carboxylic acid amide

HRID 1923493Notes

Reaction equation

[CH3:1][C:2]1[N:3]=[C:4]([CH2:10][CH2:11][C:12]2[C:13]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[N:14][O:15][C:16]=2[CH3:17])[S:5][C:6]=1[C:7](O)=[O:8].C(N1C=CN=C1)([N:26]1C=CN=C1)=O.[OH-].[NH4+]>CN(C=O)C>[CH3:1][C:2]1[N:3]=[C:4]([CH2:10][CH2:11][C:12]2[C:13]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[N:14][O:15][C:16]=2[CH3:17])[S:5][C:6]=1[C:7]([NH2:26])=[O:8]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 4-methyl-2-[2-(5-methyl-3-phenyl-isoxazol-4-yl)-ethyl]-thiazole-5-carboxylic acid (65 mg, 0.2 mmol) in DMF (82 mL) was added 1,1′-carbonyldiimidazole (39 mg, 0.24 mmol). The resulting reaction mixture was stirred for 1 h at 60° C. and then treated with an ammonium hydroxide solution (300 μL, 2.0 mmol) and stirred for 2 h at room temperature. The reaction mixture was then evaporated. Purification by chromatography (silica, dichloromethane:methanol=99:1 to 95:5) afforded the title compound (57 mg, 87%) as a white solid. MS: m/e=328.2 [M+H]+.

Workup

customThe resulting reaction mixture
stirringstirred for 2 h at room temperature
customThe reaction mixture was then evaporated
customPurification by chromatography (silica, dichloromethane:methanol=99:1 to 95:5)

Sources & evidence

ORD record: ord-c80a507d7ef5408499b24c1e27f84a28
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08178522B2

Reaction notes

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