4-Aminotetrahydropyran → HCID 46872518, compound

HRID 1942274Notes

Reaction equation

CO[C:3](=[O:24])[C:4]1[CH:9]=[CH:8][C:7](/[CH:10]=[CH:11]/[C:12]2[C:13]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[N:14][O:15][C:16]=2[CH3:17])=[N:6][CH:5]=1.[NH2:25][CH:26]1[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1>>[CH3:17][C:16]1[O:15][N:14]=[C:13]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:12]=1/[CH:11]=[CH:10]/[C:7]1[CH:8]=[CH:9][C:4]([C:3]([NH:25][CH:26]2[CH2:31][CH2:30][O:29][CH2:28][CH2:27]2)=[O:24])=[CH:5][N:6]=1

Participants

Reactant 2

HCID 4192234-Aminotetrahydropyran

HCID 46872516HCID 46872516, compound

Product 1

HCID 46872518HCID 46872518, compoundYield 77%

Procedure

As described in example 2, 6-[(E)-2-(5-methyl-3-phenyl-isoxazol-4-yl)-vinyl]-nicotinic acid methyl ester (200 mg, 0.62 mmol) instead of 6-[(E)-2-(5-methyl-3-phenyl-isoxazol-4-yl)-vinyl]-nicotinic acid methyl ester, and 4-aminotetrahydropyran instead of isopropylamine, was converted to the title compound (188 mg, 77%) which was obtained as a white solid after purification by chromatography (silica, dichloromethane:methanol 100:0 to 95:5). MS: m/e=390.4 [M+H]+.

Sources & evidence

ORD record: ord-34e09fb0f3504e3ab48e52a690a84816
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08389550B2

Reaction notes

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