Acetic Acid → HCID 136253988, compound

HRID 1043961Notes

Reaction equation

HRID 1043961 reaction equation
[OH-].[Na+].F[C:4]1[CH:9]=[C:8]([C:10]2[C:15]([CH3:16])=[CH:14][N:13]=[C:12]([O:17][CH3:18])[C:11]=2[CH3:19])[C:7]([F:20])=[CH:6][C:5]=1[C:21]1[N:25]([C@H:26]2[CH2:30][CH2:29][O:28][CH2:27]2)[N:24]=[CH:23][C:22]=1[C:31]([NH2:33])=[O:32].O.C(O)(=O)C>CS(C)=O>[F:20][C:7]1[C:8]([C:10]2[C:15]([CH3:16])=[CH:14][N:13]=[C:12]([O:17][CH3:18])[C:11]=2[CH3:19])=[CH:9][C:4]2[NH:33][C:31](=[O:32])[C:22]3[CH:23]=[N:24][N:25]([C@H:26]4[CH2:30][CH2:29][O:28][CH2:27]4)[C:21]=3[C:5]=2[CH:6]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 86686395HCID 86686395, compound

Product 1

HCID 136253988HCID 136253988, compoundYield 87.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
75 °C

Procedure

Sodium hydroxide (powder, 82 mg) was added to a solution of 5-(2,5-difluoro-4-(2-methoxy-3,5-dimethylpyridin-4-yl)phenyl)-1-[(S)-tetrahydrofuran-3-yl]-1H-pyrazole-4-carboxamide (186 mg) in DMSO (1.5 mL), and the mixture was stirred at 75° C. for 1.5 hours. The reaction mixture was cooled to room temperature, and water (5.5 mL) was then added with stirring. Acetic acid (0.12 mL) was further added, followed by stirring for 30 minutes. The generated solid was filtered, washed with water (5 mL) and then dried under reduced pressure at 60° C. for one hour to give the title compound (155 mg).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. stirringwith stirring
  3. stirringby stirring for 30 minutes
  4. filtrationThe generated solid was filtered
  5. washwashed with water (5 mL)
  6. customdried under reduced pressure at 60° C. for one hour

Sources & evidence

ORD record
ord-c9edcbbe26434871b2c3feca2965d7f6
Source dataset
uspto-grants-2013_10
Patent number
US08563565B2

Reaction notes

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