Cyanogen Bromide → HCID 86663118, compound

HRID 530316Notes

Reaction equation

HRID 530316 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:11]=[CH:12][N:13]([C:15]([N:17]([CH3:24])[CH:18]3[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]3)=[O:16])[CH:14]=2)=[CH:6][CH:5]=1.CC(C)([O-])C.[K+].[N:31]#[C:32]Br>CN(C=O)C>[C:32]([N:21]1[CH2:22][CH2:23][CH:18]([N:17]([CH3:24])[C:15]([N:13]2[CH:14]=[C:10]([C:7]3[CH:8]=[CH:9][C:4]([O:3][CH3:2])=[CH:5][CH:6]=3)[N:11]=[CH:12]2)=[O:16])[CH2:19][CH2:20]1)#[N:31]

Participants

5

Reactant 3

HCID 10476Cyanogen BromideHCID 23665647Potassium tert-butoxideHCID 66688313HCID 66688313, compound

Product 1

HCID 86663118HCID 86663118, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-(4-methoxyphenyl)-N-methyl-N-(piperidin-4-yl)-1H-imidazole-1-carboxamide hydrochloride (287 mg, 0.818 mmol) in DMF (5 mL) was added potassium tert-butoxide (184 mg, 1.636 mmol) and the mixture was allowed to stir at room temperature for 30 minutes, whereupon it was cooled in an ice/water bath and cyanogen bromide (0.818 mL, 2.454 mmol, 3 N dichloromethane solution) was added dropwise over 10-15 minutes. The reaction mixture was allowed to slowly warm up to room temperature over 1 h, and was then partitioned between water and dichloromethane/isopropanol (7:3). The layers were separated and the organic phase was further washed with water and brine, then dried (Na2SO4), filtered and the solvent was removed under reduced pressure. The residue was dissolved in the minimum volume of chloroform and insoluble material was removed by filtration. The filtrate was concentrated to give an off-white solid, (345 mg, 67%).

Workup

  1. temperaturewas cooled in an ice/water bath
  2. temperatureto slowly warm up to room temperature over 1 h
  3. customwas then partitioned between water and dichloromethane/isopropanol (7:3)
  4. customThe layers were separated
  5. washthe organic phase was further washed with water and brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. customthe solvent was removed under reduced pressure
  9. dissolutionThe residue was dissolved in the minimum volume of chloroform and insoluble material
  10. customwas removed by filtration
  11. concentrationThe filtrate was concentrated
  12. customto give an off-white solid, (345 mg, 67%)

Sources & evidence

ORD record
ord-5b44726cb3934bfa8cd94768f2626cfd
Source dataset
uspto-grants-2016_05
Patent number
US09353082B2

Reaction notes

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