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

HRID 1444630노트

반응식

HRID 1444630 반응식
[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

참가 물질

7

반응물 5

HCID 798IndoleHCID 79012-Chloro-N,N-dimethylethylamineHCID 24758Sodium hydride2회HCID 11636816N,N-Dimethylaminoethyl chloride hydrochlorideHCID 68699073Methyl 14-cyclohexyl-6-oxo-5,6,7,8-tetrahydroindolo[1,2-e][1,5]benzodiazocine-11-carboxylate

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-9fa2f88fbfa24a32875848fa761db555
출처 데이터셋
uspto-grants-2010_02
특허 번호
US07662809B2

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