2-Aminopropanol → HCID 59455877, compound

HRID 1942276Notes

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.[CH3:25][CH:26]([NH2:29])[CH2:27][OH:28]>>[OH:28][CH2:27][CH:26]([NH:29][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:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)=[N:14][O:15][C:16]=2[CH3:17])=[N:6][CH:5]=1)[CH3:25]

Participants

Reactant 2

HCID 51262-Aminopropanol

HCID 46872516HCID 46872516, compound

Product 1

HCID 59455877HCID 59455877, compoundYield 75%

Procedure

As described in example 4, 6-[(E)-2-(5-methyl-3-phenyl-isoxazol-4-yl)-vinyl]-nicotinic acid methyl ester (200 mg, 0.62 mmol), using DL-2-amino-1-propanol instead of ethanolamine, was converted to the title compound (170 mg, 75%) which was obtained as a white solid after purification by chromatography (silica, dichloromethane:methanol 100:0 to 93:7). MS: m/e=364.4 [M+H]+.

Sources & evidence

ORD record: ord-1fb2550ce8d24df2afe298fdf7beabd8
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08389550B2

Reaction notes

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