4-Aminotetrahydropyran → 6-(3-Phenyl-isoxazol-4-ylmethoxy)-N-(tetrahydro-pyran-4-yl)-nicotinamide

HRID 332023Notes

Reaction equation

HRID 332023 reaction equation
CO[C:3](=[O:23])[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][CH:20]=[CH:19][CH:18]=3)=[N:14][O:15][CH:16]=2)=[N:6][CH:5]=1.[NH2:24][CH:25]1[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1>>[C:17]1([C:13]2[C:12]([CH2:11][O:10][C:7]3[CH:8]=[CH:9][C:4]([C:3]([NH:24][CH:25]4[CH2:30][CH2:29][O:28][CH2:27][CH2:26]4)=[O:23])=[CH:5][N:6]=3)=[CH:16][O:15][N:14]=2)[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

3

Reactant 2

HCID 4192234-AminotetrahydropyranHCID 684434216-(3-Phenyl-isoxazol-4-ylmethoxy)-nicotinic acid methyl ester

Product 1

HCID 684428676-(3-Phenyl-isoxazol-4-ylmethoxy)-N-(tetrahydro-pyran-4-yl)-nicotinamideYield 73%

Procedure

As described for example 321d, 6-(3-phenyl-isoxazol-4-ylmethoxy)-nicotinic acid methyl ester (67 mg, 0.21 mmol) was converted, using 4-aminotetrahydropyran instead of isopropylamine, to the title compound (60 mg, 73%) which was obtained as an off white solid. MS: m/e=380.2 [M+H]+.

Sources & evidence

ORD record
ord-46339998ba4447b895617eca3e60f759
Source dataset
uspto-grants-2014_11
Patent number
US08877782B2

Reaction notes

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