Ethyl Acetate → 1-Methyl-6-{3-[(2-methylamino-ethyl)-pyridin-4-ylmethyl-amino]-propoxy}-1H-quinolin-2-one

HRID 1504204Notes

Reaction equation

HRID 1504204 reaction equation
C(OC(=O)C)C.Cl.C(OCC)(=O)C.C(O[C:19](=O)[N:20](C)[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>[CH3:45][N:41]1[C:42]2[C:37](=[CH:36][C:35]([O:34][CH2:33][CH2:32][CH2:31][N:23]([CH2:22][CH2:21][NH:20][CH3:19])[CH2:24][C:25]3[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=3)=[CH:44][CH:43]=2)[CH:38]=[CH:39][C:40]1=[O:46]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 21866389Hydrogen chloride-ethyl acetateHCID 86762700Methyl-(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 669605791-Methyl-6-{3-[(2-methylamino-ethyl)-pyridin-4-ylmethyl-amino]-propoxy}-1H-quinolin-2-oneYield 109.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 4N-hydrogen chloride ethyl acetate solution(48 ml) was added to an ethyl acetate solution (300 ml) of methyl-(2-{[3-(1-methyl-2-oxo-1,2-dihydro-quinolin-6-yloxy)-propyl]-pyridin-4-ylmethyl-amino}-ethyl)-carbamic acid tert-butyl ester (11.5 g), and the mixture was stirred at room temperature overnight. The reaction mixture was condensed under reduced pressure. PL-HCO3(40 g) was added to the methanol solution of the residue and followed by celite filtration. The filtrate was condensed under reduced pressure to give the title compound(9.96 g) as a brown oil.

Workup

  1. customcondensed under reduced pressure
  2. filtrationfollowed by celite filtration
  3. customcondensed under reduced pressure

Sources & evidence

ORD record
ord-5681eb3998bc4949b28d943f49628e11
Source dataset
uspto-grants-2015_12
Patent number
US09212187B2

Reaction notes

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