Ethyl Acetate → N-(4-(6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazin-1-yl)bicyclo[2.2.2]octan-1-yl)cyclopropanesulfonamide

HRID 2204554노트

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HRID 2204554 반응식
S([N:11]1[C:15]2[N:16]=[CH:17][C:18]3[N:19]([C:20]([C:23]45[CH2:30][CH2:29][C:26]([NH:31][S:32]([CH:35]6[CH2:37][CH2:36]6)(=[O:34])=[O:33])([CH2:27][CH2:28]4)[CH2:25][CH2:24]5)=[N:21][CH:22]=3)[C:14]=2[CH:13]=[CH:12]1)(C1C=CC(C)=CC=1)(=O)=O.[OH-].[Na+].CCOC(C)=O.[NH4+].[Cl-]>O1CCOCC1>[C:20]1([C:23]23[CH2:24][CH2:25][C:26]([NH:31][S:32]([CH:35]4[CH2:37][CH2:36]4)(=[O:33])=[O:34])([CH2:27][CH2:28]2)[CH2:29][CH2:30]3)[N:19]2[C:14]3[CH:13]=[CH:12][NH:11][C:15]=3[N:16]=[CH:17][C:18]2=[CH:22][N:21]=1

참가 물질

6

반응물 4

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 58010073N-(4-(6-tosyl-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazin-1-yl)bicyclo[2.2.2]octan-1-yl)cyclopropanesulfonamide

생성물 1

HCID 58009938N-(4-(6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazin-1-yl)bicyclo[2.2.2]octan-1-yl)cyclopropanesulfonamide수율 67.7%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

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온도
90 °C

실험 절차

To a solution of N-(4-(6-tosyl-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazin-1-yl)bicyclo[2.2.2]octan-1-yl)cyclopropanesulfonamide (0.025 g, 0.046 mmol) in 1,4-dioxane (3 mL) was added aqueous NaOH (2 N, 0.35 mL, 0.70 mmol). The reaction mixture was heated to about 90° C. After about 6 h, the reaction mixture was cooled to ambient temperature and EtOAc (3 mL) and saturated aqueous NH4Cl (1.5 mL) was added. The layers were separated and the organic layer was washed with water (1.5 mL) followed by brine (1.5 mL), dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure to provide N-(4-(6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazin-1-yl)bicyclo[2.2.2]octan-1-yl)cyclopropanesulfonamide as a tan solid (0.012 g, 67%). LC/MS (Table 2, Method a) Rt=1.65 min; MS m/z: 386 (M+H)+.

후처리

  1. temperaturethe reaction mixture was cooled to ambient temperature
  2. customThe layers were separated
  3. washthe organic layer was washed with water (1.5 mL)
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-38f8bd829c274b7bbc5d8e0c64f5dc37
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09365579B2

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