Potassium Carbonate → 1-methyl-6-{5-[(2-methylbenzyl)-(2-pyridin-3-ylethyl)amino]pentyl oxy}-1H-quinolin-2-one dihydrochloride

HRID 1504172Notes

Reaction equation

HRID 1504172 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH3:7][C:8]1[CH:23]=[CH:22][CH:21]=[CH:20][C:9]=1[CH2:10][NH:11][CH2:12][CH2:13][C:14]1[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=1.Br[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][O:30][C:31]1[CH:32]=[C:33]2[C:38](=[CH:39][CH:40]=1)[N:37]([CH3:41])[C:36](=[O:42])[CH:35]=[CH:34]2.C(OC(=O)C)C.[ClH:49]>C(OCC)(=O)C.CN(C=O)C>[ClH:49].[ClH:49].[CH3:41][N:37]1[C:38]2[C:33](=[CH:32][C:31]([O:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][N:11]([CH2:10][C:9]3[CH:20]=[CH:21][CH:22]=[CH:23][C:8]=3[CH3:7])[CH2:12][CH2:13][C:14]3[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=3)=[CH:40][CH:39]=2)[CH:34]=[CH:35][C:36]1=[O:42]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 21866389Hydrogen chloride-ethyl acetateHCID 60761777(2-Methylbenzyl)-(2-pyridin-3-ylethyl)amineHCID 669600336-(5-bromopentyloxy)-1-methyl-1H-quinolin-2-one

Product 1

HCID 706565531-methyl-6-{5-[(2-methylbenzyl)-(2-pyridin-3-ylethyl)amino]pentyl oxy}-1H-quinolin-2-one dihydrochloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

Potassium carbonate(360 mg) and (2-methylbenzyl)-(2-pyridin-3-ylethyl)amine(591 mg) were added to a DMF solution (6.5 ml) of 6-(5-bromopentyloxy)-1-methyl-1H-quinolin-2-one(650 mg). The mixture was stirred at 60° C. for 8 hours. Ice water was added to the reaction mixture, followed by extraction using ethyl acetate. The organic layer was washed with water and then saturated saline, dried with anhydrous sodium sulfate, and condensed under reduced pressure. The residue was purified by silica gel column chromatography (dichloromethane: ethyl acetate: methanol: aqueous ammonia=70:20:10:1). The purified product was condensed under reduced pressure. A 4N-hydrogen chloride ethyl acetate solution(1.0 ml) was added to an ethyl acetate solution(20 ml) of the residue, which was stirred at room temperature. The liquid was condensed to dryness under reduced pressure to give the title compound(270 mg) as a pale yellow amorphous solid.

Workup

  1. extractionfollowed by extraction
  2. washThe organic layer was washed with water
  3. dry with materialsaturated saline, dried with anhydrous sodium sulfate, and condensed under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (dichloromethane: ethyl acetate: methanol: aqueous ammonia=70:20:10:1)
  5. customcondensed under reduced pressure
  6. stirringwas stirred at room temperature
  7. customcondensed to dryness under reduced pressure

Sources & evidence

ORD record
ord-724a91e616ee40a1af57606f9265ed9a
Source dataset
uspto-grants-2015_12
Patent number
US09212187B2

Reaction notes

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