Methanesulfonyl chloride → 3-ethyl-4-(6-((2-(trimethylsilyl)ethoxy)methyl)-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclopentyl methanesulfonate

HRID 1969675ノート

反応式

HRID 1969675 の反応式
[S:1](Cl)([CH3:4])(=[O:3])=[O:2].[CH2:6]([CH:8]1[CH:12]([C:13]2[N:17]3[C:18]4[CH:24]=[CH:23][N:22]([CH2:25][O:26][CH2:27][CH2:28][Si:29]([CH3:32])([CH3:31])[CH3:30])[C:19]=4[N:20]=[CH:21][C:16]3=[N:15][N:14]=2)[CH2:11][C:10](=[O:33])[CH2:9]1)[CH3:7]>C(Cl)Cl>[CH3:4][S:1]([O:33][CH:10]1[CH2:11][CH:12]([C:13]2[N:17]3[C:18]4[CH:24]=[CH:23][N:22]([CH2:25][O:26][CH2:27][CH2:28][Si:29]([CH3:32])([CH3:31])[CH3:30])[C:19]=4[N:20]=[CH:21][C:16]3=[N:15][N:14]=2)[CH:8]([CH2:6][CH3:7])[CH2:9]1)(=[O:3])=[O:2]

参加物

4

反応物 2

HCID 31297Methanesulfonyl chlorideHCID 585572963-ethyl-4-(6-((2-(trimethylsilyl)ethoxy)methyl)-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclopentanone

生成物 1

HCID 585576103-ethyl-4-(6-((2-(trimethylsilyl)ethoxy)methyl)-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclopentyl methanesulfonate収率 77%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Mesyl chloride (0.067 mL, 0.866 mmol) was added dropwise to a solution of 3-ethyl-4-(6-((2-(trimethylsilyl)ethoxy)methyl)-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclopentanone (0.316 g, 0.787 mmol, Example #35 Step H) and TEA (0.219 mL, 1.57 mmol) in DCM (8 mL), and the reaction mixture was stirred at rt overnight. The solvent was removed under reduced pressure and the residue purified by silica gel column chromatography (0 to 60% EtOAc in DCM) to yield 3-ethyl-4-(6-((2-(trimethylsilyl)ethoxy)methyl)-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclopentyl methanesulfonate (0.29 g, 77%) as a white amorphous solid: LC/MS (Table 1, Method a) Rt=2.53 min; MS m/z 480 (M+H)+.

後処理

  1. customThe solvent was removed under reduced pressure
  2. customthe residue purified by silica gel column chromatography (0 to 60% EtOAc in DCM)

出典と根拠

ORDレコード
ord-cb3db01c5b8f46738bbf74e13a4b5ddf
出典データセット
uspto-grants-2013_04
特許番号
US08426411B2

反応ノート

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