2,3-Dihydro-1,4-benzodioxin-6-methylamine → 1-(2-(4-((2,3-dihydro-1,4-benzodioxin-6-ylmethyl)amino)cyclohexyl)ethyl)-7-methoxy-4-methylquinolin-2(1H)-one

HRID 39853

반응식

HRID 39853 반응식
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([CH3:25])=[CH:8][C:9](=[O:24])[N:10]2[CH2:13][CH2:14][C:15]2(C#N)[CH2:20][CH2:19][C:18](=O)[CH2:17][CH2:16]2)=[CH:5][CH:4]=1.[O:26]1[CH2:31][CH2:30][O:29][C:28]2[CH:32]=[C:33]([CH2:36][NH2:37])[CH:34]=[CH:35][C:27]1=2.C([BH3-])#N.[Na+].C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl.C(O)(=O)C.C(O)C.ClCCl>[O:26]1[C:27]2[CH:35]=[CH:34][C:33]([CH2:36][NH:37][CH:18]3[CH2:17][CH2:16][CH:15]([CH2:14][CH2:13][N:10]4[C:11]5[C:6](=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[CH:12]=5)[C:7]([CH3:25])=[CH:8][C:9]4=[O:24])[CH2:20][CH2:19]3)=[CH:32][C:28]=2[O:29][CH2:30][CH2:31]1

참가 물질

9

반응물 4

HCID 871022,3-Dihydro-1,4-benzodioxin-6-methylamineHCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 675396281-(2-(7-methoxy-4-methyl-2-oxoquinolin-1(2H)-yl)ethyl)-4-oxocyclohexanecarbonitrile

생성물 1

HCID 593984071-(2-(4-((2,3-dihydro-1,4-benzodioxin-6-ylmethyl)amino)cyclohexyl)ethyl)-7-methoxy-4-methylquinolin-2(1H)-one수율 44.7%

시약·촉매·용매 4

HCID 176Acetic Acid용매HCID 702Ethanol용매2회HCID 6212Chloroform용매HCID 6344Dichloromethane용매

반응 조건

온도
40 °C

실험 절차

To a mixture of 3 mL of ethanol and 3 mL of dichloromethane solution containing 0.18 g of 1-(2-(7-methoxy-4-methyl-2-oxoquinolin-1(2H)-yl)ethyl)-4-oxocyclohexanecarbonitrile, 1 mL of ethanol solution containing 0.13 g of (2,3-dihydrobenzo[b][1,4-]dioxin-6-yl)methylamine, 0.30 g of molecular sieves 3A, and 45 μL of acetic acid were added at room temperature. After stirred at 40° C. for 1.5 hours, the mixture was cooled to the room temperature, 36 mg of sodium cyanoborohydride was added, and stirred at the same temperature for 15 min. To the reaction mixture, aqueous saturated sodium hydrogen carbonate solution and chloroform were added, the organic layer was separated, washed with aqueous saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue thus obtained was purified by flash silica gel column chromatography [hexane:ethyl acetate=4:1], to give (A) 36 mg of 4-((2,3-dihydro-1,4-benzodioxin-6-ylmethyl)amino)-1-(2-(7-methoxy-4-methyl-2-oxo-1,2-dihydroquinolin-1-yl)ethyl)cyclohexanecarbonitrile as a colorless oil and (B) 0.11 g of 4-((2,3-dihydro-1,4-benzodioxin-6-ylmethyl)amino)-1-(2-(7-methoxy-4-methyl-2-oxo-1,2-dihydroquinolin-1-yl)ethyl)cyclohexanecarbonitrile as a white foam.

후처리

  1. additionwere added at room temperature
  2. additionwas added
  3. stirringstirred at the same temperature for 15 min
  4. customthe organic layer was separated
  5. washwashed with aqueous saturated sodium chloride solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was removed under reduced pressure
  8. customThe residue thus obtained
  9. customwas purified by flash silica gel column chromatography [hexane:ethyl acetate=4:1]

출처 및 근거

ORD 기록
ord-ad125c172a2441629fd8ab4adf51811e
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08524738B2

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