2-Amino-6-fluorobenzamide → 2-(4-bromo-1H-pyrazol-5-yl)-5-fluoroquinazolin-4(3H)-one

HRID 1469212Notes

Reaction equation

HRID 1469212 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([F:11])[C:3]=1[C:4]([NH2:6])=[O:5].[Br:12][C:13]1[CH:14]=[N:15][NH:16][C:17]=1[CH:18]=O>CC(N(C)C)=O>[Br:12][C:13]1[CH:14]=[N:15][NH:16][C:17]=1[C:18]1[NH:6][C:4](=[O:5])[C:3]2[C:2](=[CH:10][CH:9]=[CH:8][C:7]=2[F:11])[N:1]=1

Participants

4

Reactant 2

HCID 27789392-Amino-6-fluorobenzamideHCID 27821544-bromo-1H-pyrazole-5-carbaldehyde

Product 1

HCID 1363645272-(4-bromo-1H-pyrazol-5-yl)-5-fluoroquinazolin-4(3H)-oneYield 19.4%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

2-Amino-6-fluorobenzamide (77 mg, 0.50 mmol) was dissolved under argon in dimethylacetamide (5 ml), 4-bromo-1H-pyrazole-5-carbaldehyde (88 mg, 0.50 mmol) and Na2S2O5 (143 mg, 0.75 mmol) were added, and the mixture was stirred under reflux conditions for 5 h. After cooling to room temperature, the reaction mixture was concentrated and taken up with a mixture of acetonitrile and N,N-dimethylformamide. Filtration with suction and thorough drying of the remaining solid gave 2-(4-bromo-1H-pyrazol-5-yl)-5-fluoroquinazolin-4(3H)-one (30 mg, 19% of theory) as a colorless solid. 1H NMR (400 MHz, d6-DMSO δ, ppm) 13.91 (br. s, 1H, NH), 12.03 (br. s, 1H, NH), 8.22 (s, 1H), 7.80 (dd, 1H), 7.51 (d, 1H), 7.27 (dd, 1H).

Workup

  1. concentrationthe reaction mixture was concentrated
  2. additiontaken up with a mixture of acetonitrile and N,N-dimethylformamide
  3. filtrationFiltration with suction
  4. customthorough drying of the remaining solid

Sources & evidence

ORD record
ord-ac44160d43294733b1cc0122ce3bd178
Source dataset
uspto-grants-2015_04
Patent number
US09006265B2

Reaction notes

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