1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → 1-(chloromethyl)-3-[[5-[2-(dimethylamino)ethoxy]indol-2-yl]carbonyl]-5-nitro-1,2-dihydro-3H-benz[e]indole

HRID 366813

반응식

HRID 366813 반응식
C(O[C:6]([N:8]1[C:16]2[CH:15]=[C:14]([N+:17]([O-:19])=[O:18])[C:13]3[CH:20]=[CH:21][CH:22]=[CH:23][C:12]=3[C:11]=2[CH:10]([CH2:24][Cl:25])[CH2:9]1)=[O:7])(C)(C)C.Cl.[CH3:27][N:28]([CH3:44])[CH2:29][CH2:30][O:31][C:32]1[CH:33]=[C:34]2[C:38](=[CH:39][CH:40]=1)[NH:37][C:36](C(O)=O)=[CH:35]2.CCN=C=NCCCN(C)C.Cl>CC(N(C)C)=O>[Cl:25][CH2:24][CH:10]1[C:11]2[C:12]3[CH:23]=[CH:22][CH:21]=[CH:20][C:13]=3[C:14]([N+:17]([O-:19])=[O:18])=[CH:15][C:16]=2[N:8]([C:6]([C:36]2[NH:37][C:38]3[C:34]([CH:35]=2)=[CH:33][C:32]([O:31][CH2:30][CH2:29][N:28]([CH3:44])[CH3:27])=[CH:40][CH:39]=3)=[O:7])[CH2:9]1

참가 물질

5

반응물 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 153804133-(tert-butyloxycarbonyl)-1-chloromethyl-5-nitro-1,2-dihydro-3H-benz[e]indoleHCID 686908585-[2-(Dimethylamino)ethoxy]indole-2-carboxylic acid hydrochloride

생성물 1

HCID 3930681-(chloromethyl)-3-[[5-[2-(dimethylamino)ethoxy]indol-2-yl]carbonyl]-5-nitro-1,2-dihydro-3H-benz[e]indole수율 67%

시약·촉매·용매 1

HCID 31374Dimethylacetamide용매

실험 절차

Deprotection of 13 (260 mg, 0.72 mmol) as in Example C, the reaction of the product with the above 5-[2-(dimethylamino)ethoxy]indole-2-carboxylic acid hydrochloride (210 mg, 0.74 mmol), EDCI.HCl (345 mg, 1.80 mmol) and DMA (3 mL) gave crude material that was purified by precipitation from a CH2Cl2 solution at 20° C. with iPr2O (2×) to give 14e (237 mg, 67%), mp 224-227° C. 1H NMR [(CD3)2SO] δ 11.72 (d, J=1.5 Hz, 1 H, NH), 9.16 (s, 1 H, H-4), 8.35 (dd, J=7.2, 2.5 Hz, 1 H, H-6), 8.23 (dd, J=6.9, 2.5 Hz, 1 H, H-9), 7.79-7.71 (m, 1 H, H-7,8), 7.41 (d, J=8.9 Hz, 1 H, H-7'), 7.21-7.16 (m, 2 H, H-3',4', 6.94 (dd, J=9.0, 2.4 Hz, 1 H, H-6'), 4.93 (dd, J=10.6, 9.8 Hz, 1 H, H-2), 4.70 (dd, 10.9, 2.4 Hz, 1 H, H-2), 4.65-4.58 (m, 1 H, H-1), 4.18-4.09 (m, 2 H, CH2Cl), 4.07 (t, J=5.9 Hz, 2 H, OCH2), 2.66 (t, J=5.8 Hz, OCH2CH2), 2.24 (s, 6 H, N(CH3)2).

후처리

  1. customgave crude material that
  2. customwas purified by precipitation from a CH2Cl2 solution at 20° C. with iPr2O (2×)

출처 및 근거

ORD 기록
ord-151a2790cc154b909ca219df1d323179
출처 데이터셋
uspto-grants-2000_10
특허 번호
US06130237

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