4-Aminotetrahydropyran → HCID 46872639, compound

HRID 1942283Notes

Reaction equation

CO[C:3](=[O:22])[C:4]1[CH:9]=[CH:8][C:7](/[CH:10]=[CH: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](/[CH:11]=[CH: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 46872756HCID 46872756, compound

Product 1

HCID 46872639HCID 46872639, compoundYield 46%

Procedure

As described in example 9, 6-[(E)-2-(3-butyl-5-methyl-isoxazol-4-yl)-vinyl]-nicotinic acid methyl ester (100 mg, 0.28 mmol), and 4-aminotetrahydropyran instead of tetrahydrofuran-3-amine, was converted to the title compound (56 mg, 46%) which was obtained as a white solid after purification by chromatography (silica, dichloromethane:methanol 100:0 to 96.5:3.5) and trituration with isopropyl ether. MS: m/e=328.4 [M+H]+.

Sources & evidence

ORD record: ord-425e92e50afe4d8ea6c9f7b051d1e673
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08389550B2

Reaction notes

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