4-Aminotetrahydropyran → 6-((3-Butyl-5-methyl-isoxazol-4-yl)methoxy)-N-(tetrahydro-pyran-4-yl)-nicotinamide

HRID 1807496Notes

Reaction equation

CO[C:3](=[O:22])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][C:12]2[C:13]([CH2:18][CH2:19][CH2:20][CH3:21])=[N:14][O:15][C:16]=2[CH3:17])=[N:6][CH:5]=1.[NH2:23][CH:24]1[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1>>[CH2:18]([C:13]1[C:12]([CH2:11][O:10][C:7]2[CH:8]=[CH:9][C:4]([C:3]([NH:23][CH:24]3[CH2:29][CH2:28][O:27][CH2:26][CH2:25]3)=[O:22])=[CH:5][N:6]=2)=[C:16]([CH3:17])[O:15][N:14]=1)[CH2:19][CH2:20][CH3:21]

Participants

Reactant 2

HCID 4192234-Aminotetrahydropyran

HCID 665991586-(3-Butyl-5-methyl-isoxazol-4-ylmethoxy)-nicotinic acid methyl ester

Product 1

HCID 498047586-((3-Butyl-5-methyl-isoxazol-4-yl)methoxy)-N-(tetrahydro-pyran-4-yl)-nicotinamideYield 43%

Procedure

As described for example 5d, 6-(3-butyl-5-methyl-isoxazol-4-ylmethoxy)-nicotinic acid methyl ester (358 mg, 1.2 mmol) was converted, using 4-aminotetrahydropyran instead of isopropylamine, to the title compound (160 mg, 43%) which was obtained as a white solid after purification by chromatography (silica, 0 to 70% ethyl acetate in heptane). MS: m/e=374.3 [M+H]+.

Sources & evidence

ORD record: ord-d59aec65fb974a8cad156071993e4018
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08357703B2

Reaction notes

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