1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → N-[5-[(E)-3-[1-(chloromethyl)-5-nitro-1,2-dihydrobenzo[e]indol-3-yl]-3-oxo-prop-1-enyl]-1-methyl-pyrrol-3-yl]butanamide

HRID 366824

반응식

HRID 366824 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.[C:26]([NH:31][C:32]1[CH:33]=[C:34](/[CH:38]=[CH:39]/C(O)=O)[N:35]([CH3:37])[CH:36]=1)(=[O:30])[CH2:27][CH2:28][CH3:29].CCN=C=NCCCN(C)C.Cl>CC(N(C)C)=O>[C:26]([NH:31][C:32]1[CH:33]=[C:34](/[CH:38]=[CH:39]/[C:6]([N:8]2[C:16]3[CH:15]=[C:14]([N+:17]([O-:19])=[O:18])[C:13]4[CH:20]=[CH:21][CH:22]=[CH:23][C:12]=4[C:11]=3[CH:10]([CH2:24][Cl:25])[CH2:9]2)=[O:7])[N:35]([CH3:37])[CH:36]=1)(=[O:30])[CH2:27][CH2:28][CH3:29]

참가 물질

5

반응물 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 10704951(E)-4-butyramido-1-methyl-2-pyrroleacrylic acidHCID 153804133-(tert-butyloxycarbonyl)-1-chloromethyl-5-nitro-1,2-dihydro-3H-benz[e]indole

생성물 1

HCID 5469644N-[5-[(E)-3-[1-(chloromethyl)-5-nitro-1,2-dihydrobenzo[e]indol-3-yl]-3-oxo-prop-1-enyl]-1-methyl-pyrrol-3-yl]butanamide수율 62%

시약·촉매·용매 1

HCID 31374Dimethylacetamide용매

실험 절차

Deprotection of 13 (300 mg, 0.83 mmol) as in Example C above and reaction with (E)-4-butyrylamino-1-methyl-2-pyrroleacrylic acid (197 mg, 0.83 mmol), EDCI.HCl (397 mg, 2.07 mmol) and DMA gave a product that was chromatographed on silica gel. Elution with CH2Cl2 /EtOAc (1:1), followed by crystallisation from CH2Cl2 /iPr2O gave 14i (246 mg, 62%), mp 216° C. 1H NMR [(CD3)2SO] δ 9.79 (S, 1 H, NH), 9.22 (s, 1 H, H-4), 8.32 (d, J=8.7 Hz, 1 H, H-6), 8.17 (d, J=8.1 Hz, 1 H, H-9), 7.76-7.65 (m, 2 H, H-7,8), 7.64 (d, J=14.9 Hz, 1 H, COCH=CH), 7.25 (d, J=1.6 Hz, 1 H, H-5'), 6.81 (d, J=1.6 Hz, 1 H, H-3'), 6.71 (d, J=15.0 Hz, 1 H, COCH=CH), 4.65-4.50 (m, 3 H, H-1,2), 4.08 (d, J=3.6 Hz, 2 H, CH2Cl), 3.71 (s, 3 H, NCH3), 2.22 (t, J=7.3 Hz, 2 H, COCH2), 1.60 (sextet, J=7.4 Hz, 2 H, CH2CH3), 0.90 (t, J=7.4 Hz, 3 H, CH2CH3). Anal. Calculated for C25H25ClN4O4 : C, 62.4;H, 5.2; N, 11.7. Found: C, 62.6; H, 5.2; N, 11.5%.

후처리

  1. customgave a product that
  2. customwas chromatographed on silica gel
  3. washElution with CH2Cl2 /EtOAc (1:1)
  4. customfollowed by crystallisation from CH2Cl2 /iPr2O

출처 및 근거

ORD 기록
ord-92615fa00c434a509d49462e5177551a
출처 데이터셋
uspto-grants-2000_10
특허 번호
US06130237

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