Indole → Methyl 14-cyclohexyl-5-[2-(dimethylamino)ethyl]-6-oxo-5,6,7,8-tetrahydroindolo[1,2-e][1,5]benzodiazocine-11-carboxylate

HRID 1444630ノート

反応式

HRID 1444630 の反応式
[H-].[Na+].[CH:3]1([C:9]2[C:10]3[CH:11]=[CH:12][C:13]([C:29]([O:31][CH3:32])=[O:30])=[CH:14][C:15]=3[N:16]3[C:23]=2[C:22]2[CH:24]=[CH:25][CH:26]=[CH:27][C:21]=2[NH:20][C:19](=[O:28])[CH2:18][CH2:17]3)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.Cl.Cl[CH2:35][CH2:36][N:37]([CH3:39])[CH3:38].ClCCN(C)C.N1C2C(=CC=CC=2)C=C1>CN(C=O)C>[CH:3]1([C:9]2[C:10]3[CH:11]=[CH:12][C:13]([C:29]([O:31][CH3:32])=[O:30])=[CH:14][C:15]=3[N:16]3[C:23]=2[C:22]2[CH:24]=[CH:25][CH:26]=[CH:27][C:21]=2[N:20]([CH2:35][CH2:36][N:37]([CH3:39])[CH3:38])[C:19](=[O:28])[CH2:18][CH2:17]3)[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]1

参加物

7

反応物 5

HCID 798IndoleHCID 79012-Chloro-N,N-dimethylethylamineHCID 24758Sodium hydride2 回HCID 11636816N,N-Dimethylaminoethyl chloride hydrochlorideHCID 68699073Methyl 14-cyclohexyl-6-oxo-5,6,7,8-tetrahydroindolo[1,2-e][1,5]benzodiazocine-11-carboxylate

生成物 1

HCID 68699389Methyl 14-cyclohexyl-5-[2-(dimethylamino)ethyl]-6-oxo-5,6,7,8-tetrahydroindolo[1,2-e][1,5]benzodiazocine-11-carboxylate

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

NaH (1.4 eq, 60% dispersion in mineral oil) was added to a solution of methyl 14-cyclohexyl-6-oxo-5,6,7,8-tetrahydroindolo[1,2-e][1,5]benzodiazocine-11-carboxylate in DMF (0.1 M) and the solution allowed to stir at RT for 1 h. In the meantime, a 1:1 equimolar mixture of (2-chloroethyl)dimethylamine hydrochloride and NaH (60% dispersion in mineral oil) in solution in DMF (0.5 M) was prepared. After 30 mins, this mixture (2.5 eq of (2-chloroethyl)dimethylamine) was slowly added to the solution of indole anion and the mixture was stirred at RT overnight. DMF was removed in vacuo and the residue taken up in EtOAc. The organic phase was washed with H2O (twice) and then brine before being dried over Na2SO4, filtered and the solvent evaporated in vacuo. The crude compound was used in the next step without further purification; MS (ES+) m/z 474 (M+H)+.

後処理

  1. customwas prepared
  2. waitAfter 30 mins
  3. stirringthe mixture was stirred at RT overnight
  4. customDMF was removed in vacuo
  5. washThe organic phase was washed with H2O (twice) and then brine
  6. dry with materialbefore being dried over Na2SO4
  7. filtrationfiltered
  8. customthe solvent evaporated in vacuo
  9. customThe crude compound was used in the next step without further purification

出典と根拠

ORDレコード
ord-9fa2f88fbfa24a32875848fa761db555
出典データセット
uspto-grants-2010_02
特許番号
US07662809B2

反応ノート

読み込み中…