p-Toluenesulfonic acid → HCID 136379403, compound

HRID 591835Notes

Reaction equation

HRID 591835 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]=[CH:16][N:15]=1.OS([O-])=O.[Na+].CC1C=CC(S(O)(=O)=O)=CC=1>CN(C)C(=O)C>[F:12][C:7]1[CH:8]=[C:9]([F:11])[CH:10]=[C:2]2[C:3]=1[C:4](=[O:5])[NH:6][C:20]([C:18]1[CH:17]=[CH:16][N:15]=[C:14]([CH3:13])[CH:19]=1)=[N:1]2

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 27630002-METHYLISONICOTINALDEHYDEHCID 23665763Sodium BisulfiteHCID 594419592-Amino-4,6-difluorobenzamide

Product 1

HCID 136379403HCID 136379403, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
115 °C

Procedure

To a solution of 2-amino-4,6-difluoro-benzamide (0.71 g, 4.10 mmol) and 2-methyl-pyridine-4-carbaldehyde (0.50 g, 4.10 mmol) in N,N-dimethylacetamide (10 mL) were added NaHSO3 (58.5 wt %, 1.00 g, 5.70 mmol) and p-TSA (0.16 g, 0.08 mmol). The reaction mixture was heated at 115° C. for 30 hours, then cooled to room temperature. The solvent was removed under reduced pressure. The crude compound was purified by column chromatography (silica gel 230-400 mesh; 5% methanol in dichloromethane) to afford 5,7-difluoro-2-(2-methyl-pyridin-4-yl)-3H-quinazolin-4-one as a light yellow solid. Yield: 0.30 g (26%).

Workup

  1. temperaturecooled to room temperature
  2. customThe solvent was removed under reduced pressure
  3. customThe crude compound was purified by column chromatography (silica gel 230-400 mesh; 5% methanol in dichloromethane)

Sources & evidence

ORD record
ord-d06e9a2b421048db9839cfe616854c9b
Source dataset
uspto-grants-2016_01
Patent number
US09238640B2

Reaction notes

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