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

HRID 69033Notes

Reaction equation

HRID 69033 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-282bd70618ee48e1844158926954e546
Source dataset
uspto-grants-2014_09
Patent number
US08822453B2

Reaction notes

Loading…