Methyl vinyl sulfone → HCID 57670165, compound

HRID 1894493Notes

Reaction equation

HRID 1894493 reaction equation
[C:1]([C:5]1[N:10]=[CH:9][C:8]([C:11]2[N:12]([C:32]([N:34]3[CH2:39][CH2:38][CH:37]([OH:40])[CH2:36][CH2:35]3)=[O:33])[C@@:13]([C:25]3[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=3)([CH3:24])[C@@:14]([C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=3)([CH3:16])[N:15]=2)=[C:7]([O:41][CH2:42][CH3:43])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH:46]([S:48]([CH3:51])(=[O:50])=[O:49])=[CH2:47]>>[C:1]([C:5]1[N:10]=[CH:9][C:8]([C:11]2[N:12]([C:32]([N:34]3[CH2:39][CH2:38][CH:37]([O:40][CH2:47][CH2:46][S:48]([CH3:51])(=[O:50])=[O:49])[CH2:36][CH2:35]3)=[O:33])[C@@:13]([C:25]3[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=3)([CH3:24])[C@@:14]([C:17]3[CH:18]=[CH:19][C:20]([Cl:23])=[CH:21][CH:22]=3)([CH3:16])[N:15]=2)=[C:7]([O:41][CH2:42][CH3:43])[CH:6]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 3

HCID 19354Methyl vinyl sulfoneHCID 24758Sodium hydrideHCID 25262735HCID 25262735, compound

Product 1

HCID 57670165HCID 57670165, compoundYield 84.2%

Procedure

To a stirred solution of [(4S,5R)-2-(6-tert-butyl-4-ethoxy-pyridin-3-yl)-4,5-bis-(4-chloro-phenyl)-4,5-dimethyl-4,5-dihydro-imidazol-1-yl]-(4-hydroxy-piperidin-1-yl)-methanone (94.8 mg, 0.152 mmole, example 101) was added sodium hydride (9.3 mg, 0.232 mmole, 60%, Aldrich) followed by methyl vinyl sulfone (0.04 mL, 0.448 mmole, Aldrich). The mixture was allowed to stir at room temp for 2.5 h before quenched with aqueous ammonium chloride and extracted with dichloromethane. The organic extracts were washed with brine and concentrated to dryness. The crude product was purified by flash column chromatography (silica gel, eluting a gradient of 1-10% methanol in methylene chloride) to give the title compound (93.4 mg, 84% yield). HR-MS (ES, m/z) calculated for C37H47Cl2N4O5S [(M+H)+] 729.2639, observed 729.2641.

Workup

  1. custombefore quenched with aqueous ammonium chloride
  2. extractionextracted with dichloromethane
  3. washThe organic extracts were washed with brine
  4. concentrationconcentrated to dryness
  5. customThe crude product was purified by flash column chromatography (silica gel
  6. washeluting a gradient of 1-10% methanol in methylene chloride)

Sources & evidence

ORD record
ord-af44649862a549aaad27b628a547cf98
Source dataset
uspto-grants-2013_08
Patent number
US08513239B2

Reaction notes

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