Hexane → 2-[2-(phenylsulfonyl)ethylthio]-N-(2-thienyl-methyl)-3-quinoline carboxamide

HRID 1949169

Reaction equation

HRID 1949169 reaction equation
CC([O-])(C)C.[K+].[C:7]1([S:13]([CH2:16][CH2:17][SH:18])(=[O:15])=[O:14])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.Cl[C:20]1[C:29]([C:30]([NH:32][CH2:33][C:34]2[S:35][CH:36]=[CH:37][CH:38]=2)=[O:31])=[CH:28][C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[N:21]=1.CCCCCC>CN(C=O)C>[C:7]1([S:13]([CH2:16][CH2:17][S:18][C:20]2[C:29]([C:30]([NH:32][CH2:33][C:34]3[S:35][CH:36]=[CH:37][CH:38]=3)=[O:31])=[CH:28][C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[N:21]=2)(=[O:15])=[O:14])[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

6

Reactant 4

HCID 8058HexaneHCID 4470932-(Phenylsulfonyl)ethanethiolHCID 23665647Potassium tert-butoxideHCID 866453382-chloro-N-(thiophen-2-ylmethyl)quinoline-3-carboxamide

Product 1

HCID 469115922-[2-(phenylsulfonyl)ethylthio]-N-(2-thienyl-methyl)-3-quinoline carboxamideYield 70%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

112 mg (1.0 mmol) potassium tert-butylate were added to a solution of 202 mg (1.0 mmol) 2-(phenylsulfonyl)ethanethiol in DMF (6 ml) at 0° C. and the mixture was stirred for 10 min at 0° C. Then 303 mg (1.0 mmol) 2-chloro-N-(thiophen-2-ylmethyl)quinoline-3-carboxamide (precursor VVV01) were added at 0° C. and the reaction solution was heated slowly to 50° C. and stirred for 16 h at this temperature. After cooling to RT it was 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 326 mg (0.7 mmol, 70%) 2-[2-(phenylsulfonyl)ethylthio]-N-(2-thienyl-methyl)-3-quinoline carboxamide. MS: m/z 469.1 [M+H]+.

Workup

  1. temperaturethe reaction solution was heated slowly to 50° C.
  2. stirringstirred for 16 h at this temperature
  3. temperatureAfter cooling to RT it
  4. additionwas diluted with EE
  5. washwashed with a saturated aqueous NH4Cl solution
  6. extractionThe aqueous phase was extracted with EE
  7. washThe combined organic phases were washed with water and brine
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated to small volume under vacuum

Sources & evidence

ORD record
ord-048edb2dfbb94e89942963be76ab4fdb
Source dataset
uspto-grants-2013_03
Patent number
US08399673B2

Linked notes

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