Ethanolamine → 3-[(E)-2-(3-Butyl-5-methyl-isoxazol-4-yl)-vinyl]-isoxazole-5-carboxylic acid (2-hydroxy-ethyl)-amide

HRID 1920896Notes

Reaction equation

HRID 1920896 reaction equation
C(O[C:4]([C:6]1[O:10][N:9]=[C:8](/[CH:11]=[CH:12]/[C:13]2[C:14]([CH2:19][CH2:20][CH2:21][CH3:22])=[N:15][O:16][C:17]=2[CH3:18])[CH:7]=1)=[O:5])C.[CH2:23]([CH2:25][NH2:26])[OH:24].N12CCCNC1=NCCC2>C1(C)C=CC=CC=1>[OH:24][CH2:23][CH2:25][NH:26][C:4]([C:6]1[O:10][N:9]=[C:8](/[CH:11]=[CH:12]/[C:13]2[C:14]([CH2:19][CH2:20][CH2:21][CH3:22])=[N:15][O:16][C:17]=2[CH3:18])[CH:7]=1)=[O:5]

Participants

5

Reactant 3

HCID 700EthanolamineHCID 79873TriazabicyclodeceneHCID 674920753-[(E)-2-(3-Butyl-5-methyl-isoxazol-4-yl)-vinyl]-isoxazole-5-carboxylic acid ethyl ester

Product 1

HCID 468968853-[(E)-2-(3-Butyl-5-methyl-isoxazol-4-yl)-vinyl]-isoxazole-5-carboxylic acid (2-hydroxy-ethyl)-amideYield 27.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 3-[(E)-2-(3-butyl-5-methyl-isoxazol-4-yl)-vinyl]-isoxazole-5-carboxylic acid ethyl ester (70 mg, 0.23 mmol) and ethanolamine (28 mg, 0.46 mmol) in toluene (1 mL) was added 1,5,7-triazabicyclo[4.4.0]dec-5-ene (10 mg, 0.07 mmol) and the reaction stirred under argon overnight at room temperature. Then silica (1 g) was added and the mixture evaporated and the residue purified by chromatography (silica, dichloromethane:methanol=9:1 to 7:3) to afford the title compound (20 mg, 27%) which was obtained as a white solid. MS: m/e=320.1 [M+H]+.

Workup

  1. additionThen silica (1 g) was added
  2. customthe mixture evaporated
  3. customthe residue purified by chromatography (silica, dichloromethane:methanol=9:1 to 7:3)

Sources & evidence

ORD record
ord-bcd73044d6764e3c95ba214fcec0cc91
Source dataset
uspto-grants-2012_05
Patent number
US08173652B2

Reaction notes

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