Allyl bromide → (6-Allyloxy-7-methoxy-quinazolin-4-yl)-(3-chloro-4-fluoro-phenyl)-amine

HRID 1351209노트

반응식

HRID 1351209 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[C:19]3[C:14](=[CH:15][C:16]([O:21][CH3:22])=[C:17]([OH:20])[CH:18]=3)[N:13]=[CH:12][N:11]=2)[CH:5]=[CH:6][C:7]=1[F:8].C([O-])([O-])=O.[K+].[K+].[CH2:29](Br)[CH:30]=[CH2:31]>CC(C)=O>[CH2:31]([O:20][C:17]1[CH:18]=[C:19]2[C:14](=[CH:15][C:16]=1[O:21][CH3:22])[N:13]=[CH:12][N:11]=[C:10]2[NH:9][C:4]1[CH:5]=[CH:6][C:7]([F:8])=[C:2]([Cl:1])[CH:3]=1)[CH:30]=[CH2:29]

참가 물질

5

반응물 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 104712174-[(3-Chloro-4-fluorophenyl)amino]-7-methoxyquinazolin-6-ol

생성물 1

HCID 21098401(6-Allyloxy-7-methoxy-quinazolin-4-yl)-(3-chloro-4-fluoro-phenyl)-amine

시약·촉매·용매 1

HCID 180Acetone용매

반응 조건

온도
90 °C

실험 절차

To a solution of 4-(3-chloro-4-fluoro-phenylamino)-7-methoxy-quinazolin-6-ol (0.70 g, 2.18 mmol) (from Example 18, Step B, supra) in acetone (140 mL) was added K2CO3 (0.61 g, 10.9 mmol) and allyl bromide (0.94 mL, 10.9 mmol) (Aldrich). The reaction mixture was heated with stirring at 90° C. for 4 hours. The mixture was cooled to room temperature, filtered, and the filtrate was concentrated. The residue was purified by chromatography using EtOAc/CH2C2/Et3N (1:1:0.02) as eluent to give the desired (6-allyloxy-7-methoxy-quinazolin-4-yl)-(3-chloro-4-fluoro-phenyl)-amine as an off white solid. (Yield 0.64 g, 82%).

후처리

  1. temperatureThe reaction mixture was heated
  2. temperatureThe mixture was cooled to room temperature
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated
  5. customThe residue was purified by chromatography

출처 및 근거

ORD 기록
ord-c497aa9919e8410eae3113c6e13001a9
출처 데이터셋
uspto-grants-2007_05
특허 번호
US07217717B2

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