Water → HCID 67277953, compound

HRID 1696244Notes

Reaction equation

HRID 1696244 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].N12CCCN=C1CCCCC2.Br[CH2:33][CH2:34][O:35][CH3:36].O>CN(C)C=O>[CH3:36][O:35][CH2:34][CH2:33][N:10]1[C:11]2[C:12](=[C:13]3[CH:19]=[CH:18][NH:17][C:14]3=[N:15][CH:16]=2)[N:8]([C@H:3]2[CH2:4][CH2:5][CH2:6][CH2:7][C@H:2]2[CH3:1])[C:9]1=[O:20]

Participants

6

Reactant 4

HCID 962WaterHCID 809722-Bromoethyl methyl etherHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 15953425HCID 15953425, compound

Product 1

HCID 67277953HCID 67277953, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of rel-1-[(1S,2R)-2-Methylcyclohexyl]-3,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridin-2(1H)-one (20 mg) in N,N-dimethylformamide (0.5 mL) were added 1,8-diazabicyclo[5.4.0]undec-7-ene (33 μl) and 1-bromo-2-methoxyethane (21 μl). The mixture was stirred at ambient temperature for 2 hours, then 60° C. for 22 hours. To the mixture was added water. The mixture was extracted with chloroform and washed with water. The extract was dried over MgSO4, filtrated and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel with chloroform and methanol (100:0 to 90:10) to give pale yellow solid, which was triturated and washed with diisopropyl ether to give rel-3-(2-methoxyethyl)-1-[(1S,2R)-2-methylcyclohexyl]-3,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridin-2(1H)-one (4 mg) as a white powder.

Workup

  1. wait60° C. for 22 hours
  2. extractionThe mixture was extracted with chloroform
  3. washwashed with water
  4. dry with materialThe extract was dried over MgSO4
  5. filtrationfiltrated
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by column chromatography on silica gel with chloroform and methanol (100:0 to 90:10)
  8. customto give pale yellow solid, which
  9. customwas triturated
  10. washwashed with diisopropyl ether

Sources & evidence

ORD record
ord-0d939d49bb7849fd80e12ee622142725
Source dataset
uspto-grants-2012_04
Patent number
US08163767B2

Reaction notes

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