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

HRID 69029Notes

Reaction equation

HRID 69029 reaction equation
C(OC(=O)C)C.Cl.C(OC(=O)[NH:14][CH2:15][CH2:16][N:17]([CH2:25][CH2:26][CH2:27][O:28][C:29]1[CH:30]=[C:31]2[C:36](=[CH:37][CH:38]=1)[N:35]([CH3:39])[C:34](=[O:40])[CH:33]=[CH:32]2)[CH2:18][C:19]1[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=1)(C)(C)C.CO.N>C(OCC)(=O)C>[NH2:14][CH2:15][CH2:16][N:17]([CH2:25][CH2:26][CH2:27][O:28][C:29]1[CH:30]=[C:31]2[C:36](=[CH:37][CH:38]=1)[N:35]([CH3:39])[C:34](=[O:40])[CH:33]=[CH:32]2)[CH2:18][C:19]1[CH:20]=[CH:21][N:22]=[CH:23][CH:24]=1

Participants

5

Reactant 3

HCID 21705897Ammonia methanolHCID 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 8857Ethyl AcetateSolvent

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-Ammonia 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-dec831807d8147fb959588ecd8ccd13c
Source dataset
uspto-grants-2014_09
Patent number
US08822453B2

Reaction notes

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