Methylamine → N-Methyl-6-(5-methyl-3-pyrimidin-4-yl-isoxazol-4-ylmethoxy)-nicotinamide

HRID 332017Notes

Reaction equation

HRID 332017 reaction equation
[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][N:10]=[CH:9][N:8]=2)[C:3]=1[CH2:13][O:14][C:15]1[CH:23]=[CH:22][C:18]([C:19]([OH:21])=O)=[CH:17][N:16]=1.[CH3:24][NH2:25]>>[CH3:24][NH:25][C:19](=[O:21])[C:18]1[CH:22]=[CH:23][C:15]([O:14][CH2:13][C:3]2[C:4]([C:7]3[CH:12]=[CH:11][N:10]=[CH:9][N:8]=3)=[N:5][O:6][C:2]=2[CH3:1])=[N:16][CH:17]=1

Participants

3

Reactant 2

HCID 6329MethylamineHCID 684456406-(5-Methyl-3-pyrimidin-4-yl-isoxazol-4-ylmethoxy)-nicotinic acid

Product 1

HCID 68444523N-Methyl-6-(5-methyl-3-pyrimidin-4-yl-isoxazol-4-ylmethoxy)-nicotinamideYield 70%

Procedure

As described for example 313b, 6-(5-methyl-3-pyrimidin-4-yl-isoxazol-4-ylmethoxy)-nicotinic acid (53 mg, 0.17 mmol) was converted, using methylamine (2 M solution in THF) instead of isopropylamine, to the title compound (39 mg, 70%) which was obtained as a white solid. MS: m/e=326.3 [M+H]+.

Sources & evidence

ORD record
ord-f08e63106ee84ca2a02aa00eeaab7b5d
Source dataset
uspto-grants-2014_11
Patent number
US08877782B2

Reaction notes

Loading…