(R)-(-)-2-Amino-1-propanol → 6-[3-(4-Fluoro-phenyl)-isoxazol-4-ylmethoxy]-N-((R)-2-hydroxy-1-methyl-ethyl)-nicotinamide

HRID 1897331Notes

Reaction equation

HRID 1897331 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.[NH2:25][C@@H:26]([CH2:28][OH:29])[CH3:27]>>[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:25][C@H:26]([CH3:27])[CH2:28][OH:29])=[O:24])=[CH:5][N:6]=3)=[CH:16][O:15][N:14]=2)=[CH:22][CH:21]=1

Participants

3

Reactant 2

HCID 80308(R)-(-)-2-Amino-1-propanolHCID 684439776-[3-(4-Fluoro-phenyl)-isoxazol-4-ylmethoxy]-nicotinic acid methyl ester

Product 1

HCID 426305436-[3-(4-Fluoro-phenyl)-isoxazol-4-ylmethoxy]-N-((R)-2-hydroxy-1-methyl-ethyl)-nicotinamideYield 41%

Procedure

As described for example 325, 6-[3-(4-fluoro-phenyl)-isoxazol-4-ylmethoxy]-nicotinic acid methyl ester (60 mg, 0.18 mmol) was converted, using D-alaninol instead of rac-2-amino-1-propanol, to the title compound (28 mg, 41%) which was obtained as a white solid MS: m/e=372.1 [M+H]+.

Sources & evidence

ORD record
ord-aa2c6c3d362c4b699af5484223a1e330
Source dataset
uspto-grants-2013_08
Patent number
US08518974B2

Reaction notes

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