4-Aminotetrahydropyran → 6-[(3-Butyl-5-methyl-isoxazol-4-ylmethyl)-amino]-N-(tetrahydro-pyran-4-yl)-nicotinamide

HRID 1807548Notes

Reaction equation

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

Participants

Reactant 2

HCID 4192234-Aminotetrahydropyran

HCID 666435846-[(3-Butyl-5-methyl-isoxazol-4-ylmethyl)-amino]-nicotinic acid

Product 1

HCID 498016126-[(3-Butyl-5-methyl-isoxazol-4-ylmethyl)-amino]-N-(tetrahydro-pyran-4-yl)-nicotinamideYield 86%

Procedure

As described for example 19b, 6-[(3-butyl-5-methyl-isoxazol-4-ylmethyl)-amino]-nicotinic acid (70 mg, 0.24 mmol) instead of 6-(3-butyl-5-methyl-isoxazol-4-ylmethoxy)-nicotinic acid, was converted, using 4-aminotetrahydropyran instead of rac-2,2,2-trifluoro-1-(methyl)ethylamine, to the title compound (77 mg, 86%) which was obtained as an off white foam after purification by chromatography (silica, heptane:ethyl acetate=1:0 to 2:1). MS: m/e=373.3 [M+H]+.

Sources & evidence

ORD record: ord-0b559a57ec6d4b42b661e2d522c5e4cc
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08357703B2

Reaction notes

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