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Triethylamine → 4-[4-(3-Chloro-2-fluoro-phenylamino)-7-methoxy-quinazolin-6-yloxy]-cyclohexanone

HRID 1619496
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HRID 1619496 반응식
P(Cl)(Cl)(Cl)=O.O1[C:10]2([CH2:15][CH2:14][CH:13]([O:16][C:17]3[CH:18]=[C:19]4[C:24](=[CH:25][C:26]=3[O:27][CH3:28])[N:23]=[CH:22][NH:21][C:20]4=O)[CH2:12][CH2:11]2)[O:9]CC1.C(N(CC)CC)C.[Cl:37][C:38]1[C:39]([F:45])=[C:40]([CH:42]=[CH:43][CH:44]=1)[NH2:41]>C(#N)C>[Cl:37][C:38]1[C:39]([F:45])=[C:40]([NH:41][C:20]2[C:19]3[C:24](=[CH:25][C:26]([O:27][CH3:28])=[C:17]([O:16][CH:13]4[CH2:12][CH2:11][C:10](=[O:9])[CH2:15][CH2:14]4)[CH:18]=3)[N:23]=[CH:22][N:21]=2)[CH:42]=[CH:43][CH:44]=1
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참가 물질

6

반응물 4

HCID 8471Triethylamine2회HCID 24813Phosphorus oxychlorideHCID 750143-Chloro-2-fluoroaniline2회HCID 1359917776-(1,4-dioxa-spiro[4.5]dec-8-yloxy)-7-methoxy-3H-quinazolin-4-one

생성물 1

HCID 581572644-[4-(3-Chloro-2-fluoro-phenylamino)-7-methoxy-quinazolin-6-yloxy]-cyclohexanone

시약·촉매·용매 1

HCID 6342
Acetonitrile
용매
3회

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온도
40 °C

실험 절차

3.25 ml phosphorus oxychloride are added dropwise to 6.50 g 6-(1,4-dioxa-spiro[4.5]dec-8-yloxy)-7-methoxy-3H-quinazolin-4-one in 65 ml acetonitrile under an argon atmosphere. Then the reaction mixture is heated to 40° C., combined dropwise with 5.00 ml triethylamine and refluxed for 2 h. After cooling to ambient temperature 1.40 ml triethylamine and 2.60 ml 3-chloro-2-fluoro-aniline, dissolved in 5 ml acetonitrile, are added and the reaction mixture is stirred overnight at 40° C. Then a further 0.70 ml of 3-chloro-2-fluoro-aniline dissolved in 2 ml acetonitrile are added dropwise and the reaction mixture is stirred for a further 10 h. After cooling to ambient temperature the precipitate formed is suction filtered, taken up in 1 N hydrochloric acid, combined with 6 N isopropanolic hydrochloric acid and stirred at ambient temperature until the ketal cleaving is complete. The precipitate formed is suction filtered and combined with methylene chloride and 1 N sodium hydroxide solution. The aqueous phase is separated off and extracted with methylene chloride, the combined extracts are evaporated down and the flask residue is brought to crystallisation with diisopropylether.

후처리

  1. temperaturerefluxed for 2 h
  2. additionare added
  3. additionare added dropwise
  4. stirringthe reaction mixture is stirred for a further 10 h
  5. temperatureAfter cooling to ambient temperature the precipitate
  6. customformed
  7. filtrationfiltered
  8. stirringstirred at ambient temperature until the ketal cleaving
  9. customThe precipitate formed
  10. filtrationfiltered
  11. customThe aqueous phase is separated off
  12. extractionextracted with methylene chloride
  13. customthe combined extracts are evaporated down
  14. customthe flask residue is brought to crystallisation with diisopropylether

출처 및 근거

ORD 기록
ord-7960bc97a79a4753bffce8151c22da2a
출처 데이터셋
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08772298B2

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