Triphosgene → HCID 24853021, 화합물

HRID 551815노트

반응식

HRID 551815 반응식
[CH3:1][S:2]([C:5]1[CH:21]=[CH:20][C:8]([CH2:9][N:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[NH:13][CH2:12][CH2:11]2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].ClC(Cl)(O[C:26](=[O:32])OC(Cl)(Cl)Cl)Cl.Cl.Cl.[NH:36]1[CH2:40][CH2:39][CH:38]([C:41]2[CH:42]=[N:43][NH:44][CH:45]=2)[CH2:37]1.C(=O)([O-])O.[Na+]>ClCCl.CN1CCOCC1.O>[CH3:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([CH2:9][N:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[N:13]([C:26]([N:36]3[CH2:40][CH2:39][CH:38]([C:41]4[CH:42]=[N:43][NH:44][CH:45]=4)[CH2:37]3)=[O:32])[CH2:12][CH2:11]2)=[CH:20][CH:21]=1)(=[O:3])=[O:4]

참가 물질

8

반응물 4

HCID 94429TriphosgeneHCID 516892Sodium BicarbonateHCID 671872294-(pyrrolidin-3-yl)-1H-pyrazole dihydrochlorideHCID 67190176HCID 67190176, 화합물

생성물 1

HCID 24853021HCID 24853021, 화합물수율 34.6%

시약·촉매·용매 3

HCID 962Water용매HCID 6344Dichloromethane용매2회HCID 79724-Methylmorpholine용매

실험 절차

0.3 g of 4-(4-(methanesulfonyl)benzyl)-3,4-dihydro-2H-quinoxaline is dissolved in 10 ml of dichloromethane and 0.1 ml of N-methylmorpholine. 0.118 g of triphosgene is added at 0° C. and then the reaction mixture is left stirring at ambient temperature for four hours. 0.208 g of 4-(pyrrolidin-3-yl)-1H-pyrazole dihydrochloride is subsequently added and the reaction mixture is stirred for eighteen hours. A saturated solution of sodium hydrogencarbonate in water and dichloromethane are added. The aqueous phase is extracted twice with dichloromethane. The organic phases are combined, washed with water and with a saturated aqueous sodium chloride solution and dried over magnesium sulfate and then the solvent is evaporated under reduced pressure. The residue is chromatographed on silica gel, a first time with a gradient of dichloromethane/methanol 1/0 to 85/5 mixture and then a second time with a gradient of dichloromethane/ethyl acetate/methanol 1/0/0 to 70/25/5 mixture. 0.064 g of [4-(4-(methanesulfonyl)benzyl)-3,4-dihydro-2H-quinoxalin-1-yl][3-(1H-pyrazol-4-yl)pyrrolidin-1-yl]methanone is obtained.

후처리

  1. waitthe reaction mixture is left
  2. stirringthe reaction mixture is stirred for eighteen hours
  3. extractionThe aqueous phase is extracted twice with dichloromethane
  4. washwashed with water and with a saturated aqueous sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. customthe solvent is evaporated under reduced pressure
  7. customThe residue is chromatographed on silica gel

출처 및 근거

ORD 기록
ord-69b2f4177485470f923cd30c240587f0
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07947834B2

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