1-(chloromethyl)-3-[[5-[2-(dimethylamino)ethoxy]indol-2-yl]carbonyl]-5-nitro-1,2-dihydro-3H-benz[e]indole → 5-amino-1-(chloromethyl)-3-[[5-[2-(dimethylamino)ethoxy]indol-2-yl]carbonyl]-1,2-dihydro-3H-benz[e]indole

HRID 366814노트

반응식

HRID 366814 반응식
[Cl:1][CH2:2][CH:3]1[C:11]2[C:10]3[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=3[C:8]([N+:16]([O-])=O)=[CH:7][C:6]=2[N:5]([C:19]([C:21]2[NH:22][C:23]3[C:28]([CH:29]=2)=[CH:27][C:26]([O:30][CH2:31][CH2:32][N:33]([CH3:35])[CH3:34])=[CH:25][CH:24]=3)=[O:20])[CH2:4]1>C1COCC1.O=[Pt]=O>[NH2:16][C:8]1[C:9]2[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=2[C:11]2[CH:3]([CH2:2][Cl:1])[CH2:4][N:5]([C:19]([C:21]3[NH:22][C:23]4[C:28]([CH:29]=3)=[CH:27][C:26]([O:30][CH2:31][CH2:32][N:33]([CH3:34])[CH3:35])=[CH:25][CH:24]=4)=[O:20])[C:6]=2[CH:7]=1

참가 물질

4

반응물 1

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

생성물 1

HCID 3930705-amino-1-(chloromethyl)-3-[[5-[2-(dimethylamino)ethoxy]indol-2-yl]carbonyl]-1,2-dihydro-3H-benz[e]indole수율 99.4%

시약·촉매·용매 2

HCID 345198Adams' catalyst촉매HCID 8028Tetrahydrofuran용매

실험 절차

A solution of 14e (125 mg, 0.25 mmol) in THF (10 mL) was hydrogenated over PtO2 at 50 psi for 2 h. After removal of the catalyst, the solution was concentrated to a small volume under reduced pressure below 25° C. and diluted with iPr2O to give 15e (115 mg, 98%): mp >250° C.; 1H NMR [(CD3)2SO] δ 11.56 (d, J=1.4 Hz, 1 H, NH), 8.08 (d, J=8.5 Hz, 1 H, H-6), 7.76 (d, J=8.2 Hz, 1 H, H-9), 7.70 (s, 1 H, H-4), 7.46 (t, J=7.4 Hz, 1 H, H-8), 7.39 (d, J=8.9 Hz, 1 H, H-7'), 7.28 (t, J=7.7 Hz, 1 H, H-7), 7.17 (d, J=2.2 Hz, 1 H, H-4'), 7.07 (d, J=1.8 Hz, 1 H, H-3'), 6.91 (dd, J=8.9, 2.4 Hz, 1 H, H-6'), 5.98 (s, 2 H, NH2), 4.73 (dd, J=10.6, 9.1 Hz, 1 H, H-2), 4.51 (dd, J=10.9, 1.4 Hz, 1 H, H-2), 4.16-4.08 (m, 1 H, H-1), 4.06 (t, J=5.9 Hz, 2 H, OCH2), 3.98 (dd, J=10.9, 3.0 Hz, 1 H, CHHCl), 3.75 (dd, J=10.9, 8.1 Hz, 1 H, CHHCl), 2.65 (t, J=5.9 Hz, 2 H, OCH2CH2), 2.24 (s, 6 H, N(CH3)2).

후처리

  1. customAfter removal of the catalyst
  2. concentrationthe solution was concentrated to a small volume under reduced pressure below 25° C.
  3. additiondiluted with iPr2O

출처 및 근거

ORD 기록
ord-26c3e88fbaa1469fa2f3639c9b49a369
출처 데이터셋
uspto-grants-2000_10
특허 번호
US06130237

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