Cyclohexanecarboxaldehyde → (5-[cyclohexylmethyl-(2-pyridin-3-ylethyl)amino]pentyloxy}-1-methyl-1H-quinolin-2-one dihydrochloride

HRID 69003

반응식

HRID 69003 반응식
[ClH:1].Cl.C[N:4]1[C:13]2[C:8](=[CH:9][C:10]([O:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][NH:20][CH2:21][CH2:22][C:23]3[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=3)=[CH:11][CH:12]=2)[CH:7]=[CH:6][C:5]1=O.[CH:30]1([CH:36]=O)[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]1.[Na].[C:39](=[O:42])([O-])O.[Na+].C(O)C.Cl>C(OCC)(=O)C.C(O)C.ClCCCl.C(N(CC)CC)C>[ClH:1].[ClH:1].[CH:30]1([CH2:36][N:20]([CH2:21][CH2:22][C:23]2[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=2)[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][O:14][C:10]2[C:39](=[O:42])[N:4]([CH3:5])[C:13]3[C:8]([CH:9]=2)=[CH:7][CH:6]=[CH:11][CH:12]=3)[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]1

참가 물질

10

반응물 5

HCID 16275CyclohexanecarboxaldehydeHCID 516892Sodium BicarbonateHCID 5360545SodiumHCID 21887872Ethanol hydrochlorideHCID 669605681-methyl-6-[5-(2-pyridin-3-ylethylamino)pentyloxy]-1H-quinolin-2-one dihydrochloride

생성물 1

HCID 86670485(5-[cyclohexylmethyl-(2-pyridin-3-ylethyl)amino]pentyloxy}-1-methyl-1H-quinolin-2-one dihydrochloride

시약·촉매·용매 4

HCID 111,2-Dichloroethane용매HCID 702Ethanol용매HCID 8471Triethylamine용매HCID 8857Ethyl Acetate용매

실험 절차

Triethylamine (0.15 ml) was added to a 1,2-dichloroethane solution (2.5 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 30 minutes. Cyclohexane carboxaldehyde (0.073 ml) and sodium triacetoxyborohydrate (159 mg) were added thereto, and the mixture was stirred at room temperature overnight. A saturated sodium hydrogencarbonate aqueous solution was added to the reaction mixture, followed by extraction using dichloromethane. The organic layer was dried with anhydrous sodium sulfate, and condensed under reduced pressure. The residue was purified by NH silica gel column chromatography (hexane:ethyl acetate=1:1). The purified product was condensed under reduced pressure. A 1N-hydrogen chloride ethanol solution (1.0 ml) was added to an ethanol solution (20 ml) of the residue, which was stirred at room temperature. The reaction mixture was condensed under reduced pressure and ethyl acetate was added to the residue. The precipitated insoluble matter was separated, washed with ethyl acetate, and dried to give the title compound (100 mg) as a pale yellow powder.

후처리

  1. stirringthe mixture was stirred at room temperature overnight
  2. extractionfollowed by extraction
  3. dry with materialThe organic layer was dried with anhydrous sodium sulfate, and condensed under reduced pressure
  4. customThe residue was purified by NH silica gel column chromatography (hexane:ethyl acetate=1:1)
  5. customcondensed under reduced pressure
  6. stirringwas stirred at room temperature
  7. additionwas added to the residue
  8. customThe precipitated insoluble matter was separated
  9. washwashed with ethyl acetate
  10. customdried

출처 및 근거

ORD 기록
ord-7fe99b646ddc4c14942d498c8193c493
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08822453B2

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