Trifluoroacetic acid → N-Desmethyl vandetanib

HRID 238084

반응식

HRID 238084 반응식
C(O)(C(F)(F)F)=O.[Br:8][C:9]1[CH:42]=[CH:41][C:12]([NH:13][C:14]2[C:23]3[C:18](=[CH:19][C:20]([O:26][CH2:27][CH:28]4[CH2:33][CH2:32][N:31](C(OC(C)(C)C)=O)[CH2:30][CH2:29]4)=[C:21]([O:24][CH3:25])[CH:22]=3)[N:17]=[CH:16][N:15]=2)=[C:11]([F:43])[CH:10]=1>C(Cl)Cl>[Br:8][C:9]1[CH:42]=[CH:41][C:12]([NH:13][C:14]2[C:23]3[C:18](=[CH:19][C:20]([O:26][CH2:27][CH:28]4[CH2:29][CH2:30][NH:31][CH2:32][CH2:33]4)=[C:21]([O:24][CH3:25])[CH:22]=3)[N:17]=[CH:16][N:15]=2)=[C:11]([F:43])[CH:10]=1

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 11049999tert-Butyl 4-(((4-((4-bromo-2-fluorophenyl)amino)-6-methoxyquinazolin-7-yl)oxy)methyl)piperidine-1-carboxylate

생성물 1

HCID 5329048N-Desmethyl vandetanib수율 70.5%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

TFA (3 ml) was added to a suspension of 4-(4-bromo-2-fluoroanilino)-7-(1-(tert-butoxycarbonyl)piperidin-4-ylmethoxy)-6-methoxyquinazoline (673 mg, 1.2 mmol) in methylene chloride (10 ml). After stirring for 1 hour at ambient temperature, the volatiles were removed under vacuum. The residue was triturated with a mixture of water/ether. The organic layer was separated. The aqueous layer was washed again with ether. The aqueous layer was adjusted to pH10 with 2N aqueous sodium hydroxide. The aqueous layer was extracted with methylene chloride. The organic layer was dried (MgSO4) and the solvent was removed under vacuum. The solid was triturated with a mixture ether/petroleum ether (1/1), filtered, washed with ether and dried under vacuum to give 4-(4-bromo-2-fluoroanilino)-6-methoxy-7-(piperidin-4-ylmethoxy)quinazoline (390 mg, 70.5%).

후처리

  1. customthe volatiles were removed under vacuum
  2. customThe residue was triturated with a mixture of water/ether
  3. customThe organic layer was separated
  4. washThe aqueous layer was washed again with ether
  5. extractionThe aqueous layer was extracted with methylene chloride
  6. dry with materialThe organic layer was dried (MgSO4)
  7. customthe solvent was removed under vacuum
  8. customThe solid was triturated with a mixture ether/petroleum ether (1/1)
  9. filtrationfiltered
  10. washwashed with ether
  11. customdried under vacuum

출처 및 근거

ORD 기록
ord-73229ba47fdf4eeabe17ba27001fd91b
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08642608B2

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