2-Aminopropanol → 6-[3-(4-Fluoro-phenyl)-isoxazol-4-ylmethoxy]-n-(2-hydroxy-1-methyl-ethyl)-nicotinamide

HRID 83427

Reaction equation

HRID 83427 reaction equation
CO[C:3](=[O:24])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][C:12]2[C:13]([C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=3)=[N:14][O:15][CH:16]=2)=[N:6][CH:5]=1.COC(=O)C1C=CC(OCC2C(C3C=CC=CC=3)=NOC=2C)=NC=1.[NH2:49][CH:50]([CH3:53])[CH2:51][OH:52]>>[F:23][C:20]1[CH:19]=[CH:18][C:17]([C:13]2[C:12]([CH2:11][O:10][C:7]3[CH:8]=[CH:9][C:4]([C:3]([NH:49][CH:50]([CH3:53])[CH2:51][OH:52])=[O:24])=[CH:5][N:6]=3)=[CH:16][O:15][N:14]=2)=[CH:22][CH:21]=1

Participants

4

Reactant 3

HCID 51262-AminopropanolHCID 665992926-(5-Methyl-3-phenyl-isoxazol-4-ylmethoxy)-nicotinic acid methyl esterHCID 684439776-[3-(4-Fluoro-phenyl)-isoxazol-4-ylmethoxy]-nicotinic acid methyl ester

Product 1

HCID 426304206-[3-(4-Fluoro-phenyl)-isoxazol-4-ylmethoxy]-n-(2-hydroxy-1-methyl-ethyl)-nicotinamideYield 71%

Procedure

As described for example 220, 6-[3-(4-fluoro-phenyl)-isoxazol-4-ylmethoxy]-nicotinic acid methyl ester (100 mg, 0.31 mmol) was converted, instead of 6-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-nicotinic acid methyl ester, using rac-2-amino-1-propanol instead of 3-amino-1-propanol, to the title compound (80 mg, 71%) which was obtained as a colourless gum. MS: m/e=372.2 [M+H]+.

Sources & evidence

ORD record
ord-97abb7feeca04d67b0398e5880faa85b
Source dataset
uspto-grants-2014_09
Patent number
US08846719B2

Linked notes

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