Ethyl Acetate → 6-{3-[(2-aminoethyl)-N-(pyridin-4-ylmethyl)amino]propoxy}-1-methyl-1H-quinolin-2-one

HRID 1504200Notes

Reaction equation

HRID 1504200 reaction equation
C(OC(=O)C)C.Cl.C(OCC)(=O)C.C(OC(=O)[NH:20][CH2:21][CH2:22][N:23]([CH2:31][CH2:32][CH2:33][O:34][C:35]1[CH:36]=[C:37]2[C:42](=[CH:43][CH:44]=1)[N:41]([CH3:45])[C:40](=[O:46])[CH:39]=[CH:38]2)[CH2:24][C:25]1[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=1)(C)(C)C>CO>[NH2:20][CH2:21][CH2:22][N:23]([CH2:31][CH2:32][CH2:33][O:34][C:35]1[CH:36]=[C:37]2[C:42](=[CH:43][CH:44]=1)[N:41]([CH3:45])[C:40](=[O:46])[CH:39]=[CH:38]2)[CH2:24][C:25]1[CH:26]=[CH:27][N:28]=[CH:29][CH:30]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 21866389Hydrogen chloride-ethyl acetateHCID 86762698(2-{[3-(1-Methyl-2-oxo-1,2-dihydro-quinolin-6-yloxy)-propyl]-pyridin-4-ylmethyl-amino}-ethyl)-carbamic acid tert-butyl ester

Product 1

HCID 867626976-{3-[(2-aminoethyl)-N-(pyridin-4-ylmethyl)amino]propoxy}-1-methyl-1H-quinolin-2-oneYield 79.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 4N-hydrogen chloride ethyl acetate solution(0.22 ml) was added to an ethyl acetate solution (3 ml) of (2-{[3-(1-Methyl-2-oxo-1,2-dihydro-quinolin-6-yloxy)-propyl]-pyridin-4-ylmethyl-amino}-ethyl)-carbamic acid tert-butyl ester (137 mg), and the mixture was stirred at room temperature overnight. 5N-Ammoia methanol solution(1 ml) was added to the reaction mixture, and the generated insoluble matter was separated by filtration. The filtrate was condensed under reduced pressure to give the title compound(85.7 mg) as an colorless oil.

Workup

  1. customthe generated insoluble matter was separated by filtration
  2. customcondensed under reduced pressure

Sources & evidence

ORD record
ord-2f0bce1bd86e44d78617413ecf9c62f7
Source dataset
uspto-grants-2015_12
Patent number
US09212187B2

Reaction notes

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