Methanesulfonyl chloride → HCID 67346081, compound

HRID 1677420Notes

Reaction equation

HRID 1677420 reaction equation
[CH3:1][C:2]([CH3:35])([CH3:34])[C:3]([C:5]1[C:13]2[C:8](=[N:9][CH:10]=[C:11]([C:14]3[CH:19]=[CH:18][C:17]([N:20]4[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]4)=[CH:16][CH:15]=3)[N:12]=2)[N:7]([CH2:26][O:27][CH2:28][CH2:29][Si:30]([CH3:33])([CH3:32])[CH3:31])[CH:6]=1)=[O:4].C(N(C(C)C)CC)(C)C.[CH3:45][S:46](Cl)(=[O:48])=[O:47]>ClCCl>[CH3:45][S:46]([N:23]1[CH2:24][CH2:25][N:20]([C:17]2[CH:16]=[CH:15][C:14]([C:11]3[N:12]=[C:13]4[C:5]([C:3](=[O:4])[C:2]([CH3:35])([CH3:34])[CH3:1])=[CH:6][N:7]([CH2:26][O:27][CH2:28][CH2:29][Si:30]([CH3:31])([CH3:33])[CH3:32])[C:8]4=[N:9][CH:10]=3)=[CH:19][CH:18]=2)[CH2:21][CH2:22]1)(=[O:48])=[O:47]

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 67344543HCID 67344543, compound

Product 1

HCID 67346081HCID 67346081, compoundYield 87.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2,2-Dimethyl-1-[2-(4-piperazin-1-yl-phenyl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-propan-1-one (0.10 g, 0.203 mmol) in dichloromethane was added 0.042 mL of diisopropylethylamine (0.031 g, 0.244 mmol) and the reaction mixture was subsequently cooled to 0° C. Methane sulfonyl chloride (0.019 mL; 0.028 g, 0.244 mmol) was added via syringe and the reaction was slowly warmed to room temperature and stirred overnight. The reaction was quenched with water and extracted 3 times with dichloromethane. Combined organics were dried over MgSO4, filtered and conc in vacuo. Silica gel chromatography (15→65% EtOAc/hexanes over 30 minutes) afforded 0.1014 g (87% yield) of 1-[2-[4-(4-Methanesulfonyl-piperazin-1-yl)-phenyl]-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-2,2-dimethyl-propan-1-one as a yellow oil. MS (E/I): 572 (M+H).

Workup

  1. temperaturethe reaction was slowly warmed to room temperature
  2. customThe reaction was quenched with water
  3. extractionextracted 3 times with dichloromethane
  4. dry with materialCombined organics were dried over MgSO4
  5. filtrationfiltered and conc in vacuo

Sources & evidence

ORD record
ord-aa1875c8b987478c92aa96cfa739fac2
Source dataset
uspto-grants-2011_08
Patent number
US08008298B2

Reaction notes

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