Hexane → 3-[[3-[Oxo-(2-thienylmethylamino)methyl]-2-quinolyl]thio]propanoic acid methyl ester

HRID 1949168

Reaction equation

[CH3:1][O:2][C:3](=[O:7])[CH2:4][CH2:5][SH:6].CC([O-])(C)C.[K+].Cl[C:15]1[C:24]([C:25]([NH:27][CH2:28][C:29]2[S:30][CH:31]=[CH:32][CH:33]=2)=[O:26])=[CH:23][C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[N:16]=1.CCCCCC>CN(C=O)C>[CH3:1][O:2][C:3](=[O:7])[CH2:4][CH2:5][S:6][C:15]1[C:24]([C:25](=[O:26])[NH:27][CH2:28][C:29]2[S:30][CH:31]=[CH:32][CH:33]=2)=[CH:23][C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[N:16]=1

Participants

Conditions

Temperature: 50 °C

Procedure

A solution of 361 mg (3.0 mmol) 3-mercaptopropionic acid methyl ester in DMF (18 ml) was cooled to 0° C. and mixed with 336.6 mg (3.0 mmol) potassium tert-butylate and stirred for 10 min. Then 908 mg (3.0 mmol) 2-chloro-N-(thiophen-2-ylmethyl)quinoline-3-carboxamide (precursor VVV01) were added and the reaction solution was then heated slowly to 50° C. and stirred for 16 h at this temperature. It was then diluted with EE and washed with a saturated aqueous NH4Cl solution. The aqueous phase was extracted with EE. The combined organic phases were washed with water and brine, dried over Na2SO4, filtered and concentrated to small volume under vacuum. Column chromatography (hexane/EE 4:1) with the residue yielded 614 mg (1.6 mmol, 53%) 3-[[3-[oxo-(2-thienylmethylamino)methyl]-2-quinolyl]thio]propanoic acid methyl ester. MS: m/z 387.1 [M+H]+.

Workup

stirringstirred for 16 h at this temperature
additionIt was then diluted with EE
washwashed with a saturated aqueous NH4Cl solution
extractionThe aqueous phase was extracted with EE
washThe combined organic phases were washed with water and brine
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated to small volume under vacuum

Sources & evidence

ORD record: ord-5e958d3f83624a51bace6aa76ab56a90
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08399673B2

Linked notes

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