2-Aminopropanol → 2-[(e)-2-(5-Methyl-3-phenyl-isoxazol-4-yl)-vinyl]-thiazole-5-carboxylic acid (2-hydroxy-1-methyl-ethyl)-amide

HRID 1923564Notes

Reaction equation

HRID 1923564 reaction equation
C(O[C:4]([C:6]1[S:10][C:9](/[CH:11]=[CH:12]/[C:13]2[C:14]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[N:15][O:16][C:17]=2[CH3:18])=[N:8][CH:7]=1)=[O:5])C.[NH2:25][CH:26]([CH3:29])[CH2:27][OH:28]>C1(C)C=CC=CC=1>[OH:28][CH2:27][CH:26]([NH:25][C:4]([C:6]1[S:10][C:9](/[CH:11]=[CH:12]/[C:13]2[C:14]([C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)=[N:15][O:16][C:17]=2[CH3:18])=[N:8][CH:7]=1)=[O:5])[CH3:29]

Participants

4

Reactant 2

HCID 51262-AminopropanolHCID 66643683HCID 66643683, compound

Product 1

HCID 497818112-[(e)-2-(5-Methyl-3-phenyl-isoxazol-4-yl)-vinyl]-thiazole-5-carboxylic acid (2-hydroxy-1-methyl-ethyl)-amideYield 80%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a stirred solution of 2-[(E)-2-(5-methyl-3-phenyl-isoxazol-4-yl)-vinyl]-thiazole-5-carboxylic acid ethyl ester (30 mg, 0.09 mmol) in toluene (0.5 mL) was added rac-2-amino-1-propanol (9 mg, 0.12 mmol) and TBD (4 mg, 0.03 mmol). After 15 h, the reaction mixture was concentrated in vacuo then purified by chromatography (silica, 0 to 3% methanol in dichloromethane) to give the title compound (26 mg, 80%) as a white solid. MS: m/e=370.0 [M+H]+.

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. customthen purified by chromatography (silica, 0 to 3% methanol in dichloromethane)

Sources & evidence

ORD record
ord-b746a2910c664c47a40087b76bb10b29
Source dataset
uspto-grants-2012_05
Patent number
US08178522B2

Reaction notes

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