Trifluoroacetic acid → N'-methyl-N'-[3-[(5-methylindolo[3,2-b]quinolin-11-yl)amino]propyl]propane-1,3-diamine

HRID 12261Notes

Reaction equation

HRID 12261 reaction equation
C(OC(=O)[NH:7][CH2:8][CH2:9][CH2:10][N:11]([CH3:34])[CH2:12][CH2:13][CH2:14][NH:15][C:16]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[N:19]([CH3:26])[C:18]2=[C:27]3[C:32](=[N:33][C:17]=12)[CH:31]=[CH:30][CH:29]=[CH:28]3)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[CH3:34][N:11]([CH2:12][CH2:13][CH2:14][NH:15][C:16]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[N:19]([CH3:26])[C:18]2=[C:27]3[C:32](=[N:33][C:17]=12)[CH:31]=[CH:30][CH:29]=[CH:28]3)[CH2:10][CH2:9][CH2:8][NH2:7]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178483846HCID 178483846, compound

Product 1

HCID 178483776N'-methyl-N'-[3-[(5-methylindolo[3,2-b]quinolin-11-yl)amino]propyl]propane-1,3-diamineYield 101.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of [3-[methyl-[3-(5-methyl-5H-indolo[3,2-b]quinolin-11-ylamino)-propyl]amino]propyl)-carbamic acid tert-butyl ester (49 mg, 0.1 mmol) in CH2Cl2 (10 ml), was added trifluoroacetic acid (12_l). This mixture was stirred at room temperature for 16 h, at which point the reaction was completed by TLC. All solvents were removed under reduced pressure to give N1-methyl-N1-[3-(5-methyl-5H-indolo[3,2-b]quinolin-11-ylamino)propyl]propane-1,3-diamine (38 mg, 92%) as an oil, which was used directly. 1H-NMR [MeOD,_, ppm]: 8.52 (d, J=8.5 Hz, 1H), 8.35-7.73 (m, 4H), 7.63-7.60 (m, 2H), 7.31 (m, 1H), 4.45 (s, 3H, NCH3), 3.60 (m, 2H, CH2NO), 3.02 (m, 2H, CH2N(CH3)), 2.92 (s, 3H, N(CH3)), 2.36 (m, 4H, 2CH2CN(CH3)), 2.14 (m, 2H, CH2N(CH3)), 1.90 (m, 2H, CH2CN(CH3)).

Workup

  1. customAll solvents were removed under reduced pressure

Sources & evidence

ORD record
ord-f3e9c5fcd68140c49a2971d0f6558957
Source dataset
uspto-grants-2010_06
Patent number
US07728000B2

Reaction notes

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