Ethanolamine → HCID 46928466, compound

HRID 1514673Notes

Reaction equation

HRID 1514673 reaction equation
CO[C:3](=[O:25])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][C:12]2[C:13]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[N:14][O:15][C:16]=2[CH2:17][OH:18])=[N:6][CH:5]=1.[CH2:26]([CH2:28][NH2:29])[OH:27].N12CCCNC1=NCCC2>C1(C)C=CC=CC=1>[OH:27][CH2:26][CH2:28][NH:29][C:3](=[O:25])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][C:12]2[C:13]([C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)=[N:14][O:15][C:16]=2[CH2:17][OH:18])=[N:6][CH:5]=1

Participants

5

Reactant 3

HCID 700EthanolamineHCID 79873TriazabicyclodeceneHCID 66718147HCID 66718147, compound

Product 1

HCID 46928466HCID 46928466, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a stirred solution of 6-(5-hydroxymethyl-3-phenyl-isoxazol-4-ylmethoxy)-nicotinic acid methyl ester (0.11 g, 0.32 mmol) in toluene (0.5 mL) was added ethanolamine (0.03 g, 0.39 mmol) and 1,5,7-triazabicyclo[4.4.0]dec-5-ene (0.03 g, 0.17 mmol). The reaction mixture was stirred for 68 h, adsorbed on silica gel and purification by chromatography (silica, dichloromethane:methanol=100:0 to 90:10) afforded the title compound as a white solid (0.10 g, 85%). MS: m/e=370.1 [M+H]+.

Workup

  1. customadsorbed on silica gel and purification by chromatography (silica, dichloromethane:methanol=100:0 to 90:10)

Sources & evidence

ORD record
ord-893b7160cbec478d8d197db5fb672d4f
Source dataset
uspto-grants-2012_07
Patent number
US08222246B2

Reaction notes

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