Ethanolamine → 6-[3-(4-Chloro-phenyl)-isoxazol-4-ylmethoxy]N-(2-hydroxy-ethyl)-nicotinamide

HRID 83442

Reaction equation

HRID 83442 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]([CH2:13][O:14][C:15]3[CH:23]=[CH:22][C:18]([C:19]([OH:21])=O)=[CH:17][N:16]=3)=[CH:11][O:10][N:9]=2)=[CH:4][CH:3]=1.CC1ON=C(C2C=CC=CC=2)C=1COC1C=CC(C(O)=O)=CN=1.[CH2:47]([CH2:49][NH2:50])[OH:48]>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:12]([CH2:13][O:14][C:15]3[CH:23]=[CH:22][C:18]([C:19]([NH:50][CH2:49][CH2:47][OH:48])=[O:21])=[CH:17][N:16]=3)=[CH:11][O:10][N:9]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 700EthanolamineHCID 665992136-(5-Methyl-3-phenyl-isoxazol-4-ylmethoxy)-nicotinic acidHCID 684437696-[3-(4-Chloro-phenyl)-isoxazol-4-ylmethoxy]-nicotinic acid

Product 1

HCID 426305406-[3-(4-Chloro-phenyl)-isoxazol-4-ylmethoxy]N-(2-hydroxy-ethyl)-nicotinamideYield 70%

Procedure

As described for example 191, 6-[3-(4-chloro-phenyl)-isoxazol-4-ylmethoxy]-nicotinic acid (100 mg, 0.3 mmol) was converted, instead of 6-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-nicotinic acid, using ethanolamine instead of (1R,2R)-2-amino-cyclohexanol hydrochloride (1:1), to the title compound (79 mg, 70%) which was obtained as a white solid. MS: m/e=374.0 [M+H]+.

Sources & evidence

ORD record
ord-4e42414a2d05401097a871f611f3898b
Source dataset
uspto-grants-2014_09
Patent number
US08846719B2

Linked notes

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