Water → HCID 15953477, compound

HRID 1696264Notes

Reaction equation

HRID 1696264 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][NH:17][C:14]3=[N:15][CH:16]=[C:11]2[NH:10][C:9]1=[O:20].[Br:21]N1C(=O)CCC1=O.C(Cl)(Cl)Cl.O>CN(C)C=O>[Br:21][C:19]1[C:13]2[C:14](=[N:15][CH:16]=[C:11]3[NH:10][C:9](=[O:20])[N:8]([C@H:3]4[CH2:4][CH2:5][CH2:6][CH2:7][C@H:2]4[CH3:1])[C:12]3=2)[NH:17][CH:18]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6212ChloroformHCID 67184N-bromobutanimideHCID 15953425HCID 15953425, compound

Product 1

HCID 15953477HCID 15953477, compoundYield 9.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-[(1S,2R)-2-methylcyclohexyl]-3,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridin-2(1H)-one (100 mg) in N,N-dimethylformamide (1 mL) was added N-bromosuccinimide (66 mg). The mixture was stirred at ambient temperature for 2 hours. To the mixture were added chloroform and water. The mixture was extracted with chloroform. The extract was washed saturated aqueous sodium hydrogencarbonate and brine, dried over MgSO4 and filtrated. The filtrate was concentrated under reduced pressure. The residue was dissolved in a small-amount of methanol and to the solution was added EtOAc. The precipitate was filtrated and washed with EtOAc to give 8-bromo-1-[(1S,2R)-2-methylcyclohexyl]-3,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridin-2(1H)-one (12 mg) as a white powder.

Workup

  1. extractionThe mixture was extracted with chloroform
  2. washThe extract was washed saturated aqueous sodium hydrogencarbonate and brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltrated
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. dissolutionThe residue was dissolved in a small-amount of methanol
  7. additionto the solution was added EtOAc
  8. filtrationThe precipitate was filtrated
  9. washwashed with EtOAc

Sources & evidence

ORD record
ord-d1e35410a374469e8915bca52b2258bf
Source dataset
uspto-grants-2012_04
Patent number
US08163767B2

Reaction notes

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