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

HRID 591820노트

반응식

HRID 591820 반응식
[CH3:1][C:2]1[CH:7]=[C:6]([CH:8]=O)[CH:5]=[C:4]([CH3:10])[N:3]=1.[NH2:11][C:12]1[CH:20]=[C:19]([F:21])[CH:18]=[C:17]([F:22])[C:13]=1[C:14]([NH2:16])=[O:15].S([O-])(O)=O.[Na+].C1(C)C=CC(S(O)(=O)=O)=CC=1>CN(C)C(=O)C.O>[CH3:1][C:2]1[CH:7]=[C:6]([C:8]2[NH:16][C:14](=[O:15])[C:13]3[C:12](=[CH:20][C:19]([F:21])=[CH:18][C:17]=3[F:22])[N:11]=2)[CH:5]=[C:4]([CH3:10])[N:3]=1

참가 물질

7

반응물 4

HCID 6101p-Toluenesulfonic acidHCID 27630042,6-Dimethylpyridine-4-carbaldehydeHCID 23665763Sodium BisulfiteHCID 594419592-Amino-4,6-difluorobenzamide

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 31374Dimethylacetamide용매

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온도
115 °C

실험 절차

To a solution of 2,6-dimethyl-pyridine-4-carbaldehyde (5.0 g, 36.5 mmol) and 2-amino-4,6-difluorobenzamide (6.28 g, 36.5 mmol) in N,N-dimethyl acetamide (80 mL) were added sodium hydrogen sulfite (7.95 g, 43.8 mmol) and p-toluenesulfonic acid (0.7 g, 3.65 mmol). The reaction mixture was stirred at 115° C. for 16 hours under nitrogen. The reaction mixture was cooled to room temperature, diluted with water, the precipitate was collected by filtration, washed with sat. NaHCO3 and brine, and dried in vacuo to give 2-(2,6-dimethylpyridin-4-yl)-5,7-difluoro-3H-quinazolin-4-one as a white solid. Yield: 2.82 g (26.8%).

후처리

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationthe precipitate was collected by filtration
  3. washwashed with sat. NaHCO3 and brine
  4. customdried in vacuo

출처 및 근거

ORD 기록
ord-a22a555e70a545f9950e21fd82366941
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09238640B2

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