Sodium Hydroxide → N-(4-(6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)bicyclo[2.2.2]octan-1-yl)cyclopropanesulfonamide

HRID 1854383ノート

反応式

HRID 1854383 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][N:22]=3)[C:14]=2[CH:13]=[CH:12]1)(C1C=CC(C)=CC=1)(=O)=O.[OH-].[Na+].O1CCOCC1>CN(C=O)C>[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=[N:22][N:21]=1

参加物

5

反応物 3

HCID 14798Sodium HydroxideHCID 312751,4-DioxaneHCID 58009845N-(4-(6-tosyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)bicyclo[2.2.2]octan-1-yl)cyclopropanesulfonamide

生成物 1

HCID 135936812N-(4-(6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)bicyclo[2.2.2]octan-1-yl)cyclopropanesulfonamide収率 56.9%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
60 °C

実験手順

A round bottom flask was charged with N-(4-(6-tosyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)bicyclo[2.2.2]octan-1-yl)cyclopropanesulfonamide (0.27 g, 0.50 mmol), aqueous NaOH (1N, 1.0 mL, 1.0 mmol), and 1,4-dioxane (8 mL). The reaction mixture was stirred at about 60° C. for about 2 h. NH4OAc (50 mM aqueous buffer, 2 mL) and DMF (7 mL) were added and insoluble material was removed via filtration. The filtrate was purified by RP-HPLC (Table 2, Method c). The appropriate fractions were combined, the organic solvent was concentrated under reduced pressure, the resulting solid was collected by filtration, washed with water (20 mL), and lyophilized to give N-(4-(6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)bicyclo[2.2.2]octan-1-yl)cyclopropanesulfonamide as a solid (0.11 g, 56%): LC/MS (Table 2, Method a) Rt=1.53 min; MS m/z 387 (M+H)+.

後処理

  1. custominsoluble material was removed via filtration
  2. customThe filtrate was purified by RP-HPLC (Table 2, Method c)
  3. concentrationthe organic solvent was concentrated under reduced pressure
  4. filtrationthe resulting solid was collected by filtration
  5. washwashed with water (20 mL)

出典と根拠

ORDレコード
ord-31256930c6df4530aca7c4cacac3cb97
出典データセット
uspto-grants-2015_02
特許番号
US08962629B2

反応ノート

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