Water → 2-(3-Butyl-5-methyl-isoxazol-4-ylmethoxy)-thiazole-5-carboxylic acid isopropylamide

HRID 1923646Notes

Reaction equation

[H-].[Na+].[CH2:3]([C:7]1[C:11]([CH2:12][OH:13])=[C:10]([CH3:14])[O:9][N:8]=1)[CH2:4][CH2:5][CH3:6].[CH:15]([NH:18][C:19]([C:21]1[S:25][C:24](Cl)=[N:23][CH:22]=1)=[O:20])([CH3:17])[CH3:16].O>C1COCC1>[CH:15]([NH:18][C:19]([C:21]1[S:25][C:24]([O:13][CH2:12][C:11]2[C:7]([CH2:3][CH2:4][CH2:5][CH3:6])=[N:8][O:9][C:10]=2[CH3:14])=[N:23][CH:22]=1)=[O:20])([CH3:17])[CH3:16]

Participants

Conditions

Temperature: 0 °C

Procedure

To a suspension of NaH (55%, 58 mg, 2.4 mmol) in THF (3 mL) at 0° C., was added a solution of (3-butyl-5-methyl-isoxazol-4-yl)-methanol (169 mg, 1.0 mmol) in THF (3 mL) dropwise. The resulting mixture was stirred for 1 h and then cooled to 0° C. and then a solution of 2-chloro-thiazole-5-carboxylic acid isopropylamide (205 mg, 1.0 mmol) in THF (3 mL) added dropwise and the resulting mixture stirred at room temperature overnight. Water was then added and the resulting mixture extracted with ethyl acetate. The combined organic extracts were dried, filtered and concentrated. Purification by chromatography (silica, 0 to 30% methanol in dichloromethane, then 0 to 60% ethyl acetate in heptane) gave the title compound (145 mg, 43%) as a white solid. MS: m/e=338.4 [M+H]+.

Workup

stirringthe resulting mixture stirred at room temperature overnight
extractionthe resulting mixture extracted with ethyl acetate
customThe combined organic extracts were dried
filtrationfiltered
concentrationconcentrated
customPurification by chromatography (silica, 0 to 30% methanol in dichloromethane

Sources & evidence

ORD record: ord-5e80a1d9569f48a19fec74ecd6ad9c30
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08178522B2

Reaction notes

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