Hydrochloric Acid → 4-(4-Chloro-2-fluoroanilino)-6-methoxy-7-(2-([1,2,4]-triazol-1-yl)ethoxy)quinoline hydrochloride

HRID 393643

반응식

HRID 393643 반응식
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH2:15][CH2:16][N:17]3[CH:21]=[N:20][CH:19]=[N:18]3)=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][CH:3]=1.[Cl:22][C:23]1[CH:29]=[CH:28][C:26]([NH2:27])=[C:25]([F:30])[CH:24]=1.Cl>CN(C=O)C.C(O)(C)C>[ClH:1].[Cl:22][C:23]1[CH:29]=[CH:28][C:26]([NH:27][C:2]2[C:11]3[C:6](=[CH:7][C:8]([O:14][CH2:15][CH2:16][N:17]4[CH:21]=[N:20][CH:19]=[N:18]4)=[C:9]([O:12][CH3:13])[CH:10]=3)[N:5]=[CH:4][CH:3]=2)=[C:25]([F:30])[CH:24]=1

참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 938984-Chloro-2-fluoroanilineHCID 226465544-Chloro-6-methoxy-7-(2-([1,2,4]-triazol-1-yl)ethoxy)quinoline

생성물 1

HCID 226466264-(4-Chloro-2-fluoroanilino)-6-methoxy-7-(2-([1,2,4]-triazol-1-yl)ethoxy)quinoline hydrochloride수율 20.2%

시약·촉매·용매 2

HCID 3776Isopropanol용매HCID 6228Dimethylformamide용매

반응 조건

온도
150 °C

실험 절차

A solution 2 4-chloro-6-methoxy-7-(2-([1,2,4]-triazol-1-yl)ethoxy)quinoline (203 mg, 0.66 mmol), (prepared as described for the starting material in Example 38), and 4-chloro-2-fluoroaniline (74 μl, 0.66 mmol) in DMF (10 ml) containing 5M hydrogen chloride in isopropanol (0.4 ml) was heated at 150° C. for 8 hours. The volatiles were removed by evaporation and the residue was partitioned between water and methylene chloride. The aqueous layer was adjusted to pH9 with I M sodium hydroxide. The organic layer was washed with brine, dried (MgSO4) and the volatiles were removed by evaporation. The residue was dissolved in methylene chloride/methanol and 2M ethereal hydrogen chloride (1 ml) was added. After removal of the volatiles by evaporation, the residue was triturated with ether, collected by filtration, washed with ether and dried under vacuum to give 4-(4-chloro-2-fluoroanilino)-6-methoxy-7-(2-([1,2,4]-triazol-1-yl)ethoxy)quinoline hydrochloride (60 mg, 17%).

후처리

  1. customThe volatiles were removed by evaporation
  2. customthe residue was partitioned between water and methylene chloride
  3. washThe organic layer was washed with brine
  4. dry with materialdried (MgSO4)
  5. customthe volatiles were removed by evaporation
  6. dissolutionThe residue was dissolved in methylene chloride/methanol
  7. addition2M ethereal hydrogen chloride (1 ml) was added
  8. customAfter removal of the volatiles
  9. customby evaporation
  10. customthe residue was triturated with ether
  11. filtrationcollected by filtration
  12. washwashed with ether
  13. customdried under vacuum

출처 및 근거

ORD 기록
ord-b0e4b2581daf4c2ab67a502ee4c7af75
출처 데이터셋
uspto-grants-2004_10
특허 번호
US06809097B1

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