Water → HCID 67278103, compound

HRID 1696212Notes

Reaction equation

HRID 1696212 reaction equation
[CH3:1][C@@H:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C@@H:3]1[N:8]1[C:12]2=[C:13]3[CH:19]=[CH:18][N:17]([CH2:20][O:21][CH2:22][CH2:23][Si:24]([CH3:27])([CH3:26])[CH3:25])[C:14]3=[N:15][CH:16]=[C:11]2[NH:10][C:9]1=[O:28].[H-].[Na+].Br[CH2:32][C:33]1[CH:40]=[CH:39][C:36]([C:37]#[N:38])=[CH:35][CH:34]=1.O>CN(C)C=O.CCOC(C)=O>[CH3:1][C@@H:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C@@H:3]1[N:8]1[C:12]2=[C:13]3[CH:19]=[CH:18][N:17]([CH2:20][O:21][CH2:22][CH2:23][Si:24]([CH3:27])([CH3:26])[CH3:25])[C:14]3=[N:15][CH:16]=[C:11]2[N:10]([CH2:32][C:33]2[CH:40]=[CH:39][C:36]([C:37]#[N:38])=[CH:35][CH:34]=2)[C:9]1=[O:28]

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 869964-(Bromomethyl)benzonitrileHCID 67278437HCID 67278437, compound

Product 1

HCID 67278103HCID 67278103, compoundYield 90.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-[(1S,2R)-2-methylcyclohexyl]-6-{[2-(trimethylsilyl)ethoxy]methyl}-3,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridin-2(1H)-one (100 mg) in N,N-dimethylformamide (1 mL) was added 60% sodium hydride (13 mg) at 4° C. The mixture was stirred at the same temperature for 0.5 hour. To the mixture was added 4-(bromomethyl)benzonitrile (73 mg) and the solution was stirred at ambient temperature for 1 hour. To the solution was added water and EtOAc. The mixture was extracted with EtOAc and washed with brine. The extract was dried over MgSO4, filtrated and evaporated. The residue was purified by column chromatography on silica gel with EtOAc and n-hexane (1:3 to 1:1) to give 4-({1-[(1S,2R)-2-methylcyclohexyl]-2-oxo-6-{[2-(trimethylsilyl)ethoxy]methyl}-1,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridin-3(2H)-yl}methyl)benzonitrile (117 mg) as a white amorphous.

Workup

  1. stirringthe solution was stirred at ambient temperature for 1 hour
  2. extractionThe mixture was extracted with EtOAc
  3. washwashed with brine
  4. dry with materialThe extract was dried over MgSO4
  5. filtrationfiltrated
  6. customevaporated
  7. customThe residue was purified by column chromatography on silica gel with EtOAc and n-hexane (1:3 to 1:1)

Sources & evidence

ORD record
ord-d42d3901551c4f788736c08ff01468ba
Source dataset
uspto-grants-2012_04
Patent number
US08163767B2

Reaction notes

Loading…