p-Toluenesulfonic acid monohydrate → 2-(2,6-dimethylpyridin-4-yl)-5,7-difluoro-3H-quinazolin-4-one

HRID 591829Notes

Reaction equation

HRID 591829 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[C:7]([F:12])[C:3]=1[C:4]([NH2:6])=[O:5].[CH3:13][C:14]1[CH:19]=[C:18]([CH:20]=O)[CH:17]=[C:16]([CH3:22])[N:15]=1.S([O-])(O)=O.[Na+].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CN(C)C(=O)C>[CH3:13][C:14]1[CH:19]=[C:18]([C:20]2[NH:6][C:4](=[O:5])[C:3]3[C:2](=[CH:10][C:9]([F:11])=[CH:8][C:7]=3[F:12])[N:1]=2)[CH:17]=[C:16]([CH3:22])[N:15]=1

Participants

6

Reactant 4

HCID 521998p-Toluenesulfonic acid monohydrateHCID 27630042,6-Dimethylpyridine-4-carbaldehydeHCID 23665763Sodium BisulfiteHCID 594419592-Amino-4,6-difluorobenzamide

Product 1

HCID 1363480062-(2,6-dimethylpyridin-4-yl)-5,7-difluoro-3H-quinazolin-4-one

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
130 °C

Procedure

To a stirred solution of 2-amino-4,6-difluoro-benzamide (4.00 g, 0.0237 mol) and 2,6-dimethyl-pyridine-4-carbaldehyde (3.20 g, 0.0237 mol) in N,N-dimethyl acetamide (15 mL), sodium hydrogen sulfite (58.5 wt %, 5.05 g, 0.0284 mol), and p-toluene sulfonic acid monohydrate (0.90 g, 4.74 mmol) were added and the reaction mixture was stirred at 130° C. for 16 hours. The solvent was evaporated in vacuo, water was added, and the precipitated solid was filtered to give 2-(2,6-dimethyl-pyridin-4-yl)-5,7-difluoro-3H-quinazolin-4-one as a yellow solid, which was used in the next step without further purification. Yield: 3.70 g (54.3%).

Workup

  1. customThe solvent was evaporated in vacuo, water
  2. additionwas added
  3. filtrationthe precipitated solid was filtered

Sources & evidence

ORD record
ord-76b85ab9ba064ca493e7c7f46da8ae69
Source dataset
uspto-grants-2016_01
Patent number
US09238640B2

Reaction notes

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