N,N-Dimethylethylenediamine → 8-(2-Dimethylamino-ethylcarbamoyloxy)-3-(4-fluorobenzoyl)-1,1-dimethyl-1,2,3,6-tetrahydroazepino[4,5-B]indole-5-carboxylic acid ethyl ester

HRID 736091

반응식

HRID 736091 반응식
ClC(Cl)(O[C:5](=[O:11])[O:6][C:7](Cl)(Cl)Cl)Cl.[CH2:13]([O:15][C:16]([C:18]1[C:24]2[NH:25][C:26]3[CH:27]=C(O)[CH:29]=[CH:30][C:31]=3[C:23]=2[C:22]([CH3:34])([CH3:33])[CH2:21][N:20]([C:35](=[O:43])[C:36]2[CH:41]=[CH:40][C:39]([F:42])=[CH:38][CH:37]=2)[CH:19]=1)=[O:17])[CH3:14].C(N(C(C)C)CC)(C)C.[CH3:53][N:54]([CH3:58])[CH2:55][CH2:56][NH2:57]>C(Cl)Cl>[CH2:13]([O:15][C:16]([C:18]1[C:24]2[NH:25][C:26]3[CH:27]=[C:7]([O:6][C:5](=[O:11])[NH:57][CH2:56][CH2:55][N:54]([CH3:58])[CH3:53])[CH:29]=[CH:30][C:31]=3[C:23]=2[C:22]([CH3:34])([CH3:33])[CH2:21][N:20]([C:35](=[O:43])[C:36]2[CH:37]=[CH:38][C:39]([F:42])=[CH:40][CH:41]=2)[CH:19]=1)=[O:17])[CH3:14]

참가 물질

6

반응물 4

HCID 66053N,N-DimethylethylenediamineHCID 81531DiisopropylethylamineHCID 94429TriphosgeneHCID 666409793-(4-Fluorobenzoyl)-8-hydroxy-1,1-dimethyl-1,2,3,6-tetrahydroazepino[4,5-b]indole-5-carboxylic acid ethyl ester

생성물 1

HCID 102566598-(2-Dimethylamino-ethylcarbamoyloxy)-3-(4-fluorobenzoyl)-1,1-dimethyl-1,2,3,6-tetrahydroazepino[4,5-B]indole-5-carboxylic acid ethyl ester수율 28.9%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Triphosgene (58 mg, 0.195 mmol) was added to a stirred solution of 3-(4-fluorobenzoyl)-8-hydroxy-1,1-dimethyl-1,2,3,6-tetrahydroazepino[4,5-b]indole-5-carboxylic acid ethyl ester (49 mg, 0.116 mmol) and diisopropylethylamine (0.8 mL, 4.01 mmol) in dry DCM (10 mL) at 0° C. under N2. The resulting mixture was stirred at ambient temperature for 1.5 hours, and N,N-dimethylethylenediamine (0.1 mL, 0.91 mmol) was added. The mixture was stirred at ambient temperature overnight. The solvents were removed in vacuo, and the residue was purified by preparative reverse-phase HPLC to give the title compound (18 mg); 1H-NMR (CDCl3): 10.63 (1H, s), 7.76 (2H, m), 7.63-7.60 (2H, m), 7.16-7.11 (3H, m), 6.88-6.86 (1H, dd), 5.61 (1H, t), 4.24 (2H, q), 4.10 (2H, brs), 3.37 (2H, m), 2.48 (2H, m), 2.27 (6H, s), 1.59 (6H, s), 1.24 (3H, t); MS (ES): 537 (MH+).

후처리

  1. stirringThe mixture was stirred at ambient temperature overnight
  2. customThe solvents were removed in vacuo
  3. customthe residue was purified by preparative reverse-phase HPLC

출처 및 근거

ORD 기록
ord-fd51195461884665b3becd496c31a586
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07595311B2

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