Dimethyl Sulfoxide → 8-Chloro-1-(4-oxo-cyclohexyl)-4H,6H-2,3,5,10b-tetraaza-benzo[e]azulene-5-carboxylic acid tert-butyl ester

HRID 1255453노트

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HRID 1255453 반응식
C(Cl)(=O)C(Cl)=O.CS(C)=O.[C:11]([O:15][C:16]([N:18]1[CH2:27][C:26]2[N:22]([C:23]([C@H:28]3[CH2:33][CH2:32][C@H:31]([OH:34])[CH2:30][CH2:29]3)=[N:24][N:25]=2)[C:21]2[CH:35]=[CH:36][C:37]([Cl:39])=[CH:38][C:20]=2[CH2:19]1)=[O:17])([CH3:14])([CH3:13])[CH3:12].C(N(CC)CC)C>ClCCl>[C:11]([O:15][C:16]([N:18]1[CH2:27][C:26]2[N:22]([C:23]([CH:28]3[CH2:29][CH2:30][C:31](=[O:34])[CH2:32][CH2:33]3)=[N:24][N:25]=2)[C:21]2[CH:35]=[CH:36][C:37]([Cl:39])=[CH:38][C:20]=2[CH2:19]1)=[O:17])([CH3:14])([CH3:12])[CH3:13]

참가 물질

6

반응물 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 178451485HCID 178451485, 화합물

생성물 1

HCID 584587428-Chloro-1-(4-oxo-cyclohexyl)-4H,6H-2,3,5,10b-tetraaza-benzo[e]azulene-5-carboxylic acid tert-butyl ester수율 90%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

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온도
-50 °C

실험 절차

To a solution of oxalyl chloride (0.11 ml, 1.3 mmol) in dichloromethane (8 ml) was added dimethylsulfoxide (0.21 ml, 2.6 mmol) at −60° C. The mixture was stirred for 5 minutes at −50° C. A solution of cis/trans-8-chloro-1-(4-hydroxy-cyclohexyl)-4H,6H-2,3,5,10b-tetraaza-benzo[e]azulene-5-carboxylic acid tert-butyl ester (0.046 g, 1.1 mmol) in dichloromethane (3 ml) was added at −65° C. Stirring for 30 minutes was followed by addition of triethylamine (0.77 ml, 5.5 mmol). The cooling bath was removed 5 minutes after completed addition, and the reaction mixture was stirred for 1 h. The reaction mixture was washed with one portion of aqueous saturated ammonium chloride solution. The aqueous layer was extracted with three portions of tert-butyl methyl ether. The combined organic layers were dried over anhydrous sodium sulfate and concentrated in vacuo. Flash-chromatography with n-heptane/ethyl acetate as eluent gave the title compound (0.41 g, 90%) as white solid. MS m/e: 417 ([[M+H]]+)

후처리

  1. stirringStirring for 30 minutes
  2. customThe cooling bath was removed 5 minutes
  3. additionaddition
  4. stirringthe reaction mixture was stirred for 1 h
  5. washThe reaction mixture was washed with one portion of aqueous saturated ammonium chloride solution
  6. extractionThe aqueous layer was extracted with three portions of tert-butyl methyl ether
  7. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  8. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-c20aa9f3b85e4bc6ab8c8e2757311e01
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08461151B2

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