Pyridine → 3-[(Phenylsulfonyl)amino]-n-(2,4,6-trimethyl-3-pyrrolidin-1-ylphenyl)thiophene-2-carboxamide

HRID 2105285ノート

反応式

HRID 2105285 の反応式
[NH2:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7]([NH:9][C:10]1[C:15]([CH3:16])=[CH:14][C:13]([CH3:17])=[C:12]([N:18]2[CH2:22][CH2:21][CH2:20][CH2:19]2)[C:11]=1[CH3:23])=[O:8].N1C=CC=CC=1.[C:30]1([S:36](Cl)(=[O:38])=[O:37])[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>ClCCl.Cl>[C:30]1([S:36]([NH:1][C:2]2[CH:6]=[CH:5][S:4][C:3]=2[C:7]([NH:9][C:10]2[C:15]([CH3:16])=[CH:14][C:13]([CH3:17])=[C:12]([N:18]3[CH2:19][CH2:20][CH2:21][CH2:22]3)[C:11]=2[CH3:23])=[O:8])(=[O:38])=[O:37])[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

参加物

6

反応物 3

HCID 1049PyridineHCID 7369Benzenesulfonyl chlorideHCID 865967603-amino-N-(2,4,6-trimethyl-3-pyrrolidin-1-ylphenyl)thiophene-2-carboxamide

生成物 1

HCID 252531443-[(Phenylsulfonyl)amino]-n-(2,4,6-trimethyl-3-pyrrolidin-1-ylphenyl)thiophene-2-carboxamide

試薬・触媒・溶媒 2

HCID 313Hydrochloric Acid溶媒HCID 6344Dichloromethane溶媒

実験手順

To a solution of the carboxamide (0.304 mmol) of step 1 above in dichloromethane (5 mL) in a 25 ml round bottom flask was added pyridine (0.304 mmol) and benzenesulfonyl chloride (0.304 mmol). The reaction mixture was stirred at room temperature for 18 hours. The reaction mixture was then diluted with hydrochloric acid (2N) and extracted with dichloromethane (2×15 mL). The combined organic extracts were washed with a saturated aqueous solution of sodium bicarbonate (2×10 mL). The organic layers were then dried with magnesium sulfate, filtered, and concentrated under reduced pressure to yield a brown oil. The oil was further purified by silica gel chromatography using 5% ethyl acetate in hexanes as the mobile phase to yield ′3-[(phenylsulfonyl)amino]-N-(2,4,6-trimethyl-3-pyrrolidin-1-ylphenyl)thiophene-2-carboxamide as a white to yellow solid.

後処理

  1. extractionextracted with dichloromethane (2×15 mL)
  2. washThe combined organic extracts were washed with a saturated aqueous solution of sodium bicarbonate (2×10 mL)
  3. dry with materialThe organic layers were then dried with magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customto yield a brown oil
  7. customThe oil was further purified by silica gel chromatography

出典と根拠

ORDレコード
ord-ecf71992dd9e429ea1baec01c494340f
出典データセット
uspto-grants-2009_08
特許番号
US07579340B2

反応ノート

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