N-[2-[1-(chloromethyl)-5-nitro-1,2-dihydrobenzo[e]indole-3-carbonyl]-1H-indol-5-yl]acetamide → N-[2-[5-amino-1-(chloromethyl)-1,2-dihydrobenzo[e]indole-3-carbonyl]-1H-indol-5-yl]acetamide

HRID 366809Notes

Reaction equation

HRID 366809 reaction equation
[C:1]([NH:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9]([C:14]([N:16]1[C:24]3[CH:23]=[C:22]([N+:25]([O-])=O)[C:21]4[CH:28]=[CH:29][CH:30]=[CH:31][C:20]=4[C:19]=3[CH:18]([CH2:32][Cl:33])[CH2:17]1)=[O:15])=[CH:8]2)(=[O:3])[CH3:2]>C1COCC1.O=[Pt]=O>[C:1]([NH:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9]([C:14]([N:16]1[C:24]3[CH:23]=[C:22]([NH2:25])[C:21]4[CH:28]=[CH:29][CH:30]=[CH:31][C:20]=4[C:19]=3[CH:18]([CH2:32][Cl:33])[CH2:17]1)=[O:15])=[CH:8]2)(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 4365483N-[2-[1-(chloromethyl)-5-nitro-1,2-dihydrobenzo[e]indole-3-carbonyl]-1H-indol-5-yl]acetamide

Product 1

HCID 392734N-[2-[5-amino-1-(chloromethyl)-1,2-dihydrobenzo[e]indole-3-carbonyl]-1H-indol-5-yl]acetamideYield 89%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 14c (170 mg, 0.37 mmol) in THF (60 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 EtOAc/iPr2O to give 15c (141 mg, 89%). mp >300° C. 1H NMR [(CD3)2SO] δ 11.61 (d, J=1.4 Hz, 1 H, indole NH), 9.84 (s, 1 H, NHCO), 8.08 (d, J=8.5 Hz, 1 H, H-6), 8.05 (d, J=1.4 Hz, 1 H, H-4'), 7.76 (d, J=8.2 Hz, 1 H, H-9), 7.71 (s, 1 H, H-4), 7.46 (t, J=7.5 Hz, 1 H, H-8), 7.42 (d, J=8.9 Hz, 1 H, H-7'), 7.33 (dd, J=8.8, 1.9 Hz, 1 H, H-6'), 7.29 (t, J=7.5 Hz, 1 H, H-7), 7.14 (d, J=1.7 Hz, 1 H, H-3'), 5.98 (s, 2 H, NH2), 4.74 (dd, J=10.8, 9.0 Hz, 1 H, H-2), 4.51 (dd, J=11.0, 1.6 Hz, 1 H, H-2), 4.17-4.08 (m, 1 H, H-1), 3.97 (dd, J=11.0, 3.0 Hz, 1 H, CHHCl), 3.77 (dd, J=10.9, 7.8 Hz, 1 H, CHHCl), 2.06 (s, 3 H, CH3).

Workup

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

Sources & evidence

ORD record
ord-d6b78616aecf4e9db658cf39b7d27f13
Source dataset
uspto-grants-2000_10
Patent number
US06130237

Reaction notes

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