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 2204554ノート

反応式

HRID 2204554 の反応式
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

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

反応条件

温度
90 °C

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-38f8bd829c274b7bbc5d8e0c64f5dc37
出典データセット
uspto-grants-2016_06
特許番号
US09365579B2

反応ノート

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