Dichloromethane → 1-[5-(1-Methyl-2-oxo-1,2-dihydro-quinolin-6-yloxy)-pentyl]-3-phenyl-1-(2-pyridin-3-yl-ethyl)-urea hydrochloride

HRID 69038Notes

Reaction equation

HRID 69038 reaction equation
C(N(C(C)C)C(C)C)C.[Cl:10]CCl.Cl.Cl.[CH3:15][N:16]1[C:25]2[C:20](=[CH:21][C:22]([O:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][NH:32][CH2:33][CH2:34][C:35]3[CH:36]=[N:37][CH:38]=[CH:39][CH:40]=3)=[CH:23][CH:24]=2)[CH:19]=[CH:18][C:17]1=[O:41].[C:42]1([N:48]=[C:49]=[O:50])[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1>C1(C)C=CC=CC=1>[ClH:10].[CH3:15][N:16]1[C:25]2[C:20](=[CH:21][C:22]([O:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][N:32]([CH2:33][CH2:34][C:35]3[CH:36]=[N:37][CH:38]=[CH:39][CH:40]=3)[C:49]([NH:48][C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)=[O:50])=[CH:23][CH:24]=2)[CH:19]=[CH:18][C:17]1=[O:41]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 7672Phenyl isocyanateHCID 81531DiisopropylethylamineHCID 669605681-methyl-6-[5-(2-pyridin-3-ylethylamino)pentyloxy]-1H-quinolin-2-one dihydrochloride

Product 1

HCID 867627031-[5-(1-Methyl-2-oxo-1,2-dihydro-quinolin-6-yloxy)-pentyl]-3-phenyl-1-(2-pyridin-3-yl-ethyl)-urea hydrochloride

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

N-Ethyldiisopropylamine (0.192 ml) was added to a dichloromethane solution (5 ml) of 1-methyl-6-[5-(2-pyridin-3-ylethylamino)pentyloxy]-1H-quinolin-2-one dihydrochloride (219 mg). The mixture was stirred at room temperature for 5 minutes. The reaction mixture was condensed under reduced pressure. Phenylisocyanate (0.065 ml) and toluene (2 ml) were added to the residue. The mixture was stirred at 100° C. for 1 hour. The reaction mixture was purified by NH silica gel column chromatography (ethyl acetate:hexane=1:1→1:0). The purified product was concentrated under reduced pressure. A 1N-hydrogen chloride ethanol solution was added to the solution of the residue in ethanol, and stirred for 30 minutes at room temperature. The precipitated insoluble matter was collected by filtration, washed with ethyl acetate, and dried to give the title compound (147 mg) as a pale yellow flakes.

Workup

  1. customcondensed under reduced pressure
  2. stirringThe mixture was stirred at 100° C. for 1 hour
  3. customThe reaction mixture was purified by NH silica gel column chromatography (ethyl acetate:hexane=1:1→1:0)
  4. concentrationThe purified product was concentrated under reduced pressure
  5. additionA 1N-hydrogen chloride ethanol solution was added to the solution of the residue in ethanol
  6. stirringstirred for 30 minutes at room temperature
  7. filtrationThe precipitated insoluble matter was collected by filtration
  8. washwashed with ethyl acetate
  9. customdried

Sources & evidence

ORD record
ord-9dc273438bda435fb24fb6b3e9ef373d
Source dataset
uspto-grants-2014_09
Patent number
US08822453B2

Reaction notes

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