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

HRID 1949169

反応式

HRID 1949169 の反応式
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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
0 °C

実験手順

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]+.

後処理

  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

出典と根拠

ORDレコード
ord-048edb2dfbb94e89942963be76ab4fdb
出典データセット
uspto-grants-2013_03
特許番号
US08399673B2

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