Dichloromethane → N-[2-(2,3,4,5-tetrahydroazepino[4,5-b]indol-6(1H)-yl)ethyl]benzenesulfonamide hydrochloride

HRID 1370403ノート

反応式

HRID 1370403 の反応式
[C:1]1([S:7]([NH:10][CH2:11][CH2:12][N:13]2[C:21]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[C:15]3[CH2:22][CH2:23][N:24](C(OC(C)(C)C)=O)[CH2:25][CH2:26][C:14]2=3)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(C(O)=O)(F)(F)F.C(Cl)[Cl:42]>>[ClH:42].[CH2:22]1[C:15]2[C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:21]=3[N:13]([CH2:12][CH2:11][NH:10][S:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)(=[O:8])=[O:9])[C:14]=2[CH2:26][CH2:25][NH:24][CH2:23]1

参加物

4

反応物 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 22396576tert-butyl 6-{2-[(phenylsulfonyl)amino]ethyl}-1,4,5,6-tetrahydroazepino[4,5-b]indole-3(2H)-carboxylate

生成物 1

HCID 22396661N-[2-(2,3,4,5-tetrahydroazepino[4,5-b]indol-6(1H)-yl)ethyl]benzenesulfonamide hydrochloride収率 90%

実験手順

tert-Butyl 6-{2-[(phenylsulfonyl)amino]ethyl}-1,4,5,6-tetrahydroazepino[4,5-b]indole-3(2H)-carboxylate (0.0430 g, 0.0916 mmol) was dissolved in CH2Cl2 (2 mL) at rt. CF3CO2H (1 mL) was added, then the reaction mixture was stirred for 2 h. The reaction mixture was concentrated and the residue was taken up in EtOAc (2 mL). HCl in Et2O (1N) (2 mL) was added and the precipitated salt was collected by filtration. N-[2-(2,3,4,5-tetrahydroazepino[4,5-b]indol-6(1H)-yl)ethyl]benzenesulfonamide hydrochloride (0.0335 g) was obtained in 90% yield. 1H NMR (300 MHz, CD3OD) δ 3.16, 3.19-3.23, 3.37-3.41, 3.44-3.47, 3.53-3.57, 4.34, 7.08, 7.15, 7.32, 7.49, 7.52, 7.61, 7.77; MS (ESI+) for C20H23N3O2S m/z 370.1 (M+H)+.

後処理

  1. concentrationThe reaction mixture was concentrated
  2. additionHCl in Et2O (1N) (2 mL) was added
  3. filtrationthe precipitated salt was collected by filtration

出典と根拠

ORDレコード
ord-7bb99f66666e43558055f4e9185fcefa
出典データセット
uspto-grants-2003_06
特許番号
US06583135B2

反応ノート

読み込み中…