1-(Oxan-3-yl)methanamine--hydrogen chloride (1/1) → 6-(5-Methyl-3-phenyl-isoxazol-4-ylmethoxy)-N-(tetrahydro-pyran-3-ylmethyl)-nicotinamide

HRID 332284Notes

Reaction equation

HRID 332284 reaction equation
[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH: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.Cl.[O:25]1[CH2:30][CH2:29][CH2:28][CH:27]([CH2:31][NH2:32])[CH2:26]1>>[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:3]=1[CH2:13][O:14][C:15]1[CH:23]=[CH:22][C:18]([C:19]([NH:32][CH2:31][CH:27]2[CH2:28][CH2:29][CH2:30][O:25][CH2:26]2)=[O:21])=[CH:17][N:16]=1

Participants

3

Reactant 2

HCID 226481201-(Oxan-3-yl)methanamine--hydrogen chloride (1/1)HCID 665992136-(5-Methyl-3-phenyl-isoxazol-4-ylmethoxy)-nicotinic acid

Product 1

HCID 684450056-(5-Methyl-3-phenyl-isoxazol-4-ylmethoxy)-N-(tetrahydro-pyran-3-ylmethyl)-nicotinamideYield 25%

Procedure

As described for example 8b, 6-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-nicotinic acid (100 mg, 0.32 mmol) was converted, using (tetrahydro-2-H-pyran-3-yl)methanamine hydrochloride instead of methylamine, to the title compound (33 mg, 25%) which was obtained as a white solid after crystallisation from ethyl acetate:hexane. MS: m/e=408.4 [M+H]+.

Sources & evidence

ORD record
ord-39a5176905144ff7ba0faf9d231174de
Source dataset
uspto-grants-2014_11
Patent number
US08877783B2

Reaction notes

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