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 1969675Notes

Reaction equation

HRID 1969675 reaction equation
[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]

Participants

4

Reactant 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

Product 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 methanesulfonateYield 77%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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)+.

Workup

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

Sources & evidence

ORD record
ord-cb3db01c5b8f46738bbf74e13a4b5ddf
Source dataset
uspto-grants-2013_04
Patent number
US08426411B2

Reaction notes

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