1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → 1-(chloromethyl)-3-[[6-[2-(dimethylamino)ethoxy]-5-methoxyindol-2-yl]carbonyl]-5-nitro-1,2-dihydro-3H-benz[e]indole

HRID 366818

반응식

HRID 366818 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]([CH3:46])[CH2:29][CH2:30][O:31][C:32]1[CH:40]=[C:39]2[C:35]([CH:36]=[C:37](C(O)=O)[NH:38]2)=[CH:34][C:33]=1[O:44][CH3:45].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:37]2[NH:38][C:39]3[C:35]([CH:36]=2)=[CH:34][C:33]([O:44][CH3:45])=[C:32]([O:31][CH2:30][CH2:29][N:28]([CH3:27])[CH3:46])[CH:40]=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 697033546-[2-(Dimethylamino)ethoxy]-5-methoxyindole-2-carboxylic acid hydrochloride

생성물 1

HCID 104144181-(chloromethyl)-3-[[6-[2-(dimethylamino)ethoxy]-5-methoxyindol-2-yl]carbonyl]-5-nitro-1,2-dihydro-3H-benz[e]indole수율 48%

시약·촉매·용매 1

HCID 31374Dimethylacetamide용매

실험 절차

Deprotection of 13 (260 mg, 0.72 mmol) as in Example C, and reaction of the product with 6-[2-(dimethylamino)ethoxy]-5-methoxyindole-2-carboxylic acid hydrochloride (230 mg, 0.73 mmol), EDCI.HCl (345 mg, 1.80 mmol) and DMA (3 mL) at 20° C. for 3 h gave a solid. This was shaken with dilute KHCO3 and the resulting gelatinous solid was collected and chromatographed on alumina-90. Elution with EtOAc/MeOH (10:1) provided the crude product which was recrystallised from EtOAc/i-Pr2O, followed by CH2Cl2 /petroleum ether, to give 14f (180 mg, 48%), mp 224-234 (C (dec.). 1H NMR [(CD3)2SO] δ 11.54 (d, J=1.6 Hz, 1 H, NH), 9.17 (s, 1 H, H-4), 8.34 (dd, J=7.5, 2.2 Hz, 1 H, H-6), 8.22 (dd, J=7.1, 1.8 Hz, 1 H, H-9), 7.79-7.69 (m, 2 H, H-7,8), 7.17 (d, J=1.6 Hz, 1 H, H-3'), 7.16 (s, 1 H, H-4' or 7'), 6.99 (s, 1 H, H-4' or 7'), 4.91 (t, J=10.2 Hz, 1 H, H-2), 4.68 (dd, J=10.9, 2.4 Hz, 1 H, H-2), 4.65-4.57 (m, 1 H, H-1), 4.17-4.09 (m, 2 H, CH2Cl), 4.06 (t, J=6.0 Hz, 2 H, OCH2), 3.79 (s, 3 H, OCH3), 2.69 (t, J=5.9 Hz, 2 H, OCH2CH2), 2.26 (s, 6 H, N(CH3)2).

후처리

  1. customgave a solid
  2. customthe resulting gelatinous solid was collected
  3. customchromatographed on alumina-90
  4. washElution with EtOAc/MeOH (10:1)
  5. customprovided the crude product which
  6. customwas recrystallised from EtOAc/i-Pr2O

출처 및 근거

ORD 기록
ord-db58e7af3142446397f548e6de0f32ce
출처 데이터셋
uspto-grants-2000_10
특허 번호
US06130237

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