2-Aminopropanol → HCID 46944263, compound

HRID 1807526Notes

Reaction equation

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

Participants

Reactant 2

HCID 51262-Aminopropanol

HCID 66643566HCID 66643566, compound

Product 1

HCID 46944263HCID 46944263, compoundYield 73%

Conditions

Temperature: 50 °C

Procedure

A mixture of 6-(3-cyclohexyl-5-methyl-isoxazol-4-ylmethoxy)-nicotinic acid methyl ester (500 mg, 1.1 mmol), rac-2-amino-1-propanol (95 mg, 1.3 mmol) and TBD (44 mg, 0.31 mmol) was heated at 50° C. for 15 h under argon. The reaction mixture was concentrated onto silica then purified by chromatography (silica, 0 to 5% methanol in dichloromethane) to give the title compound (290 mg, 73%) as a white solid. MS: m/e=374.4 [M+H]+.

Workup

concentrationThe reaction mixture was concentrated onto silica
customthen purified by chromatography (silica, 0 to 5% methanol in dichloromethane)

Sources & evidence

ORD record: ord-5246db228ab94077bc2bbe85dcfe2d30
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08357703B2

Reaction notes

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