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Pyrrolidine → Benzo[b]thiophene-2-sulfonic acid {2-[2-methoxy-5-(2-pyrrolidin-1-yl-ethanesulfonyl)-benzenesulfonylamino]-phenyl}-amide

HRID 730225
ノート
印刷プレビュー

反応式

HRID 730225 の反応式
[CH:1]([S:3]([C:6]1[CH:7]=[CH:8][C:9]([O:35][CH3:36])=[C:10]([S:12]([NH:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[NH:22][S:23]([C:26]2[S:30][C:29]3[CH:31]=[CH:32][CH:33]=[CH:34][C:28]=3[CH:27]=2)(=[O:25])=[O:24])(=[O:14])=[O:13])[CH:11]=1)(=[O:5])=[O:4])=[CH2:2].[NH:37]1[CH2:41][CH2:40][CH2:39][CH2:38]1>C1COCC1.C(Cl)Cl>[CH3:36][O:35][C:9]1[CH:8]=[CH:7][C:6]([S:3]([CH2:1][CH2:2][N:37]2[CH2:41][CH2:40][CH2:39][CH2:38]2)(=[O:4])=[O:5])=[CH:11][C:10]=1[S:12]([NH:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[NH:22][S:23]([C:26]1[S:30][C:29]2[CH:31]=[CH:32][CH:33]=[CH:34][C:28]=2[CH:27]=1)(=[O:25])=[O:24])(=[O:13])=[O:14]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 31268PyrrolidineHCID 86605045Benzo[b]thiophene-2-sulfonic acid [2-(5-ethenesulfonyl-2-methoxybenzenesulfonylamino)phenyl] amide

生成物 1

HCID 11686009Benzo[b]thiophene-2-sulfonic acid {2-[2-methoxy-5-(2-pyrrolidin-1-yl-ethanesulfonyl)-benzenesulfonylamino]-phenyl}-amide

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran
溶媒

実験手順

To a solution of benzo[b]thiophene-2-sulfonic acid [2-(5-ethenesulfonyl-2-methoxybenzenesulfonylamino)phenyl]-amide (0.2 mmol, prepared as in Example 19) in dry THF (2 mL) was added 0.2 mL of pyrrolidine. The resulting reaction mixture was stirred at room temperature for 1 h. The reaction mixture was diluted with DCM (10 mL) and was washed with saturated sodium chloride aqueous solution (25 mL). The organic phase was dried over anhydrous sodium sulfate and concentrated under vacuum. The residue obtained was purified by flash column chromatography eluting with EtOAc then DCM/methanol/AcOH (100:2:1 to 100:10:2) to furnish 121 mg of benzo[b]thiophene-2-sulfonic acid {2-[2-methoxy-5-(2-pyrrolidin-1-yl-ethanesulfonyl)-benzenesulfonylamino]phenyl} amide. LC: Tr 0.94 min; MS: 636.8 (M+1)+. 1H NMR (CDCl3, 400 MHz): δ 1.68 (m, 4H), 2.38 (m, 4H), 2.78(t, 2H), 3.28 (t, 2H), 4.20 (s, 3H), 6.76 (d, 1H), 6.96 (d, 1H), 7.14 (t, 1H), 7.21 (d, 1H), 7.36 (d, 1H), 7.41 (t, 1H), 7.49(t, 1H), 7.60 (s, 1H), 7.79 (d, 1H), 7.83 (d, 1H), 8.07 (d, 1H), 8.26 (d, 1H) ppm.

後処理

  1. customThe resulting reaction mixture
  2. washwas washed with saturated sodium chloride aqueous solution (25 mL)
  3. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  4. concentrationconcentrated under vacuum
  5. customThe residue obtained
  6. customwas purified by flash column chromatography
  7. washeluting with EtOAc

出典と根拠

ORDレコード
ord-38c2dc68d58147aea58165d3ba1e96ad
出典データセット
uspto-grants-2009_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07582673B2

反応ノート

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