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 1969675노트

반응식

HRID 1969675 반응식
[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]

참가 물질

4

반응물 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

생성물 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 methanesulfonate수율 77%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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)+.

후처리

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

출처 및 근거

ORD 기록
ord-cb3db01c5b8f46738bbf74e13a4b5ddf
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08426411B2

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