Triphosgene → HCID 24853021、化合物

HRID 551815ノート

反応式

HRID 551815 の反応式
[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]

参加物

8

反応物 4

HCID 94429TriphosgeneHCID 516892Sodium BicarbonateHCID 671872294-(pyrrolidin-3-yl)-1H-pyrazole dihydrochlorideHCID 67190176HCID 67190176、化合物

生成物 1

HCID 24853021HCID 24853021、化合物収率 34.6%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6344Dichloromethane溶媒2 回HCID 79724-Methylmorpholine溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-69b2f4177485470f923cd30c240587f0
出典データセット
uspto-grants-2011_05
特許番号
US07947834B2

反応ノート

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