Acetic Acid → HCID 89648407, compound

HRID 1774518Notes

Reaction equation

HRID 1774518 reaction equation
C[O-].[Na+].[CH3:4][N:5]([CH3:21])[C:6]1[N:10]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[F:18])[N:9]=[C:8]([C:19]#[N:20])[CH:7]=1.[Cl-:22].[NH4+:23].C(O)(=O)C>CO>[ClH:22].[CH3:4][N:5]([CH3:21])[C:6]1[N:10]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[F:18])[N:9]=[C:8]([C:19](=[NH:23])[NH2:20])[CH:7]=1

Participants

6

Reactant 4

HCID 176Acetic Acid2×HCID 25517Ammonium Chloride2×HCID 10942334Sodium MethoxideHCID 89662143HCID 89662143, compound

Product 1

HCID 89648407HCID 89648407, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

356 mg of sodium methanolate (6.60 mmol, 4.0 eq.) were dissolved in 10 mL of methanol. 403 mg of 5-(dimethylamino)-1-(2-fluorobenzyl)-1H-pyrazole-3-carbonitrile 1-11-1 (1.65 mmol, 1.0 eq.) were dissolved in 20 mL of methanol and added dropwise. The mixture was stirred for one hour at rt. 111.2 mg of ammonium chloride (2.08 mmol, 1.26 eq.) and 377 μL of 100% acetic acid (6.60 mmol, 4.0 eq.) were added and stirred under reflux for 24 hours. 111 mg of ammonium chloride (2.08 mmol, 1.26 eq.) and 377 μL of 100% acetic acid (6.60 mmol, 4.0 eq.) were added and stirred under reflux for 24 hours again. The mixture was concentrated under vacuo. The residue was suspended in acetonitrile and filtered off two times. The filter cakes were dissolved in DCM/methanol 1:1 and filtered over a silica column to provide 313 mg (1.19 mmol, 72.6%) of analytically pure target compound.

Workup

  1. additionadded dropwise
  2. stirringstirred
  3. temperatureunder reflux for 24 hours
  4. stirringstirred
  5. temperatureunder reflux for 24 hours again
  6. concentrationThe mixture was concentrated under vacuo
  7. filtrationfiltered off two times
  8. dissolutionThe filter cakes were dissolved in DCM/methanol 1:1
  9. filtrationfiltered over a silica column
  10. customto provide 313 mg (1.19 mmol, 72.6%) of analytically pure target compound

Sources & evidence

ORD record
ord-d109e9770b7f4124936700013c3d4a22
Source dataset
uspto-grants-2016_02
Patent number
US09260412B2

Reaction notes

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