Benzenesulfonyl chloride → HCID 66908232、化合物

HRID 1691553ノート

反応式

HRID 1691553 の反応式
Cl.[S:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]1[NH2:11].[C:12]1([S:18]([Cl:21])(=[O:20])=[O:19])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>N1C=CC=CC=1>[ClH:21].[S:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]1[NH:11][S:18]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)(=[O:20])=[O:19]

参加物

4

反応物 2

HCID 7369Benzenesulfonyl chloride2 回HCID 66907303Thieno[3,2-b]pyridin-2-ylamine hydrochloride

生成物 1

HCID 66908232HCID 66908232、化合物収率 25.2%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

To a suspension of compound 146-A (0.65 g, 2.91 mmol) in pyridine (30 mL), at rt, was added benzenesulfonyl chloride (0.751 mL, 5.83 mmol), and the reaction was stirred for 16 h. Additional benzenesulfonyl chloride (0.225 mL, 1.76 mmol) was added and the reaction mixture was stirred at rt for an additional 16 h. The solvent was evaporated in vacuo, the residue treated with 1N HCl and extracted several times with dichloromethane and ethyl acetate. The aqueous layer was filtered, dissolved in methanol, and the combined organic extracts were evaporated in vacuo. The resultant residue was purified by reverse phase HPLC, eluting with an MeCN—H2O gradient to afford compound 146-B as an orange solid (0.24 g, 20%). 1H-NMR (CD3CN): δ 6.92 (s, 1H), 7.2 8.0 (d of d, 1H), 7.46 (m, 2H), 7.56 (m, 1H), 7.85 (m, 2H), 8.27 (d, 1H), 8.35 (d, 1H); MS: m/z 291.09 (MH+).

後処理

  1. stirringthe reaction mixture was stirred at rt for an additional 16 h
  2. customThe solvent was evaporated in vacuo
  3. additionthe residue treated with 1N HCl
  4. extractionextracted several times with dichloromethane and ethyl acetate
  5. filtrationThe aqueous layer was filtered
  6. dissolutiondissolved in methanol
  7. customthe combined organic extracts were evaporated in vacuo
  8. customThe resultant residue was purified by reverse phase HPLC
  9. washeluting with an MeCN—H2O gradient

出典と根拠

ORDレコード
ord-b0e86f9535dd494babb110b56c6d557d
出典データセット
uspto-grants-2012_04
特許番号
US08153682B2

反応ノート

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