Hydrochloric Acid → HCID 86690498, compound

HRID 1026769Notes

Reaction equation

HRID 1026769 reaction equation
[CH:1]1([N:5]([CH2:14][C:15]2[CH:20]=[CH:19][N:18]=[C:17]([C:21]3[CH:26]=[CH:25][C:24]([F:27])=[C:23]([OH:28])[CH:22]=3)[CH:16]=2)[C:6]([C:8]2[N:9]=[CH:10][N:11]([CH3:13])[CH:12]=2)=[O:7])[CH2:4][CH2:3][CH2:2]1.[Cl:29][C:30]([F:35])([F:34])C([O-])=O.[Na+].C(=O)([O-])[O-].[Cs+].[Cs+].[ClH:43].[OH-].[Na+]>O.CN(C)C=O>[ClH:29].[ClH:43].[CH:1]1([N:5]([CH2:14][C:15]2[CH:20]=[CH:19][N:18]=[C:17]([C:21]3[CH:26]=[CH:25][C:24]([F:27])=[C:23]([O:28][CH:30]([F:35])[F:34])[CH:22]=3)[CH:16]=2)[C:6]([C:8]2[N:9]=[CH:10][N:11]([CH3:13])[CH:12]=2)=[O:7])[CH2:2][CH2:3][CH2:4]1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 10796Cesium carbonateHCID 14798Sodium HydroxideHCID 2734985Sodium chlorodifluoroacetateHCID 86690499HCID 86690499, compound

Product 1

HCID 86690498HCID 86690498, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of N-cyclobutyl-N-{[2-(4-fluoro-3-hydroxyphenyl)pyridin-4-yl]methyl}-1-methyl-1H-imidazole-4-carboxamide (200 mg), sodium chlorodifluoroacetate (190 mg), cesium carbonate (241 mg), dimethylformamide (1.5 mL) and water (0.15 mL) was stirred while heating at 100° C. for 5 hr. After the reaction mixture was cooled in ice, concentrated hydrochloric acid (0.2 mL) was added thereto, and the resulting mixture was stirred for 1 hr. After addition of an aqueous solution of 2M sodium hydroxide, the mixture was extracted with ethyl acetate. The organic phase was separated out, and the solvent was distilled off under reduced pressure. The resulting residue was purified by HPLC. The resulting residue was dissolved in acetonitrile, and 4N hydrochloric acid/ethyl acetate was added thereto, followed by concentration to afford the title compound (30 mg).

Workup

  1. temperatureAfter the reaction mixture was cooled in ice
  2. stirringthe resulting mixture was stirred for 1 hr
  3. extractionthe mixture was extracted with ethyl acetate
  4. customThe organic phase was separated out
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe resulting residue was purified by HPLC
  7. dissolutionThe resulting residue was dissolved in acetonitrile
  8. addition4N hydrochloric acid/ethyl acetate was added
  9. concentrationfollowed by concentration

Sources & evidence

ORD record
ord-415912be560940b7ae72087d773f6f25
Source dataset
uspto-grants-2014_05
Patent number
US08729271B2

Reaction notes

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