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

HRID 1923555Notes

Reaction equation

HRID 1923555 reaction equation
CO[C:3]([C:5]1[S:9][C:8]([CH2:10][CH2:11][C:12]2[C:13]([CH2:18][CH2:19][CH2:20][CH3:21])=[N:14][O:15][C:16]=2[CH3:17])=[N:7][CH:6]=1)=[O:4].[NH2:22][CH:23]([CH3:26])[CH2:24][OH:25]>C1(C)C=CC=CC=1>[OH:25][CH2:24][CH:23]([NH:22][C:3]([C:5]1[S:9][C:8]([CH2:10][CH2:11][C:12]2[C:13]([CH2:18][CH2:19][CH2:20][CH3:21])=[N:14][O:15][C:16]=2[CH3:17])=[N:7][CH:6]=1)=[O:4])[CH3:26]

Participants

4

Reactant 2

HCID 51262-AminopropanolHCID 66643644HCID 66643644, compound

Product 1

HCID 497822752-[2-(3-Butyl-5-methyl-isoxazol-4-yl)-ethyl]-thiazole-5-carboxylic acid (2-hydroxy-1-methyl-ethyl)-amideYield 44%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a stirred solution of 2-[2-(3-butyl-5-methyl-isoxazol-4-yl)-ethyl]-thiazole-5-carboxylic acid methyl ester (170 mg, 0.55 mmol) in toluene (0.5 mL) was added rac-2-amino-1-propanol (83 mg, 1.1 mmol) and TBD (23 mg, 0.017 mmol). After 15 h the reaction mixture was concentrated in vacuo then purified by chromatography (silica, 0 to 7% methanol in dichloromethane) to give the title compound (85 mg, 44%) as a pale yellow oil.

Workup

  1. concentrationAfter 15 h the reaction mixture was concentrated in vacuo
  2. customthen purified by chromatography (silica, 0 to 7% methanol in dichloromethane)

Sources & evidence

ORD record
ord-ce1d3a03225c4b76a674d59d3bd6e915
Source dataset
uspto-grants-2012_05
Patent number
US08178522B2

Reaction notes

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