Acetic Acid → HCID 86705364, compound

HRID 536491Notes

Reaction equation

HRID 536491 reaction equation
C[O-].[Na+].[F:4][C:5]1[CH:22]=[CH:21][CH:20]=[CH:19][C:6]=1[CH2:7][C:8]1[N:9]=[C:10]([C:17]#[N:18])[N:11]2[CH:16]=[CH:15][CH:14]=[N:13][C:12]=12.C(O)(=O)C.[Cl-].[NH4+:28]>CO>[F:4][C:5]1[CH:22]=[CH:21][CH:20]=[CH:19][C:6]=1[CH2:7][C:8]1[N:9]=[C:10]([C:17](=[NH:28])[NH2:18])[N:11]2[CH:16]=[CH:15][CH:14]=[N:13][C:12]=12

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 25517Ammonium ChlorideHCID 10942334Sodium MethoxideHCID 71285885HCID 71285885, compound

Product 1

HCID 86705364HCID 86705364, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Under argon atmosphere, 6.98 g (32.30 mmol) of sodium methylate (25% solution in methanol) was put in 50 ml methanol and 8.000 g (30.76 mmol) of 8-(2-fluorobenzyl)imidazo[1,5-a]pyrimidine-6-carbonitrile dissolved in 40 ml of absolute methanol was added. The reaction mixture was stirred for 1 h at RT. 7.205 g (119.98 mmol) of acetic acid and 1.975 g (36.92 mmol) of ammonium chloride were added and the mixture was stirred for 2 h at 50° C. The reaction mixture was concentrated by evaporation and the residue was distributed between 150 ml water and 100 ml ethyl acetate. The aqueous phase was made basic (pH=10) with 2N sodium hydroxide solution and the phases were stirred for 1 h at RT. Water was added and it was extracted three times with ethyl acetate. The combined organic phases were dried over sodium sulphate, concentrated by evaporation and the residue was dried under high vacuum. 7.53 g (purity 73%, 66% of theor.) of the target compound was obtained.

Workup

  1. additionwas added
  2. stirringthe mixture was stirred for 2 h at 50° C
  3. concentrationThe reaction mixture was concentrated by evaporation
  4. stirringthe phases were stirred for 1 h at RT
  5. additionWater was added
  6. extractionit was extracted three times with ethyl acetate
  7. dry with materialThe combined organic phases were dried over sodium sulphate
  8. concentrationconcentrated by evaporation
  9. customthe residue was dried under high vacuum
  10. custom7.53 g (purity 73%, 66% of theor.) of the target compound was obtained

Sources & evidence

ORD record
ord-f649ae9934c94b79bc633f4e2ee9df8b
Source dataset
uspto-grants-2014_10
Patent number
US08859569B2

Reaction notes

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