Water → N-{4-[(2-Aminopyridin-4-yl)oxy]-3-fluorophenyl}-N'-(4-fluorophenyl)cyclopropane-1,1-dicarboxamide

HRID 2265680노트

반응식

HRID 2265680 반응식
[F:1][C:2]1[CH:17]=[C:16]([NH:18][C:19]([C:21]2([C:24](=[O:33])[NH:25][C:26]3[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=3)[CH2:23][CH2:22]2)=[O:20])[CH:15]=[CH:14][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7](C(N)=O)[CH:6]=1.O.FC(F)(F)C(OI(C1C=CC=CC=1)OC(=O)C(F)(F)F)=O.[N:56]1C=CC=CC=1>CN(C)C=O>[NH2:56][C:7]1[CH:6]=[C:5]([O:4][C:3]2[CH:14]=[CH:15][C:16]([NH:18][C:19]([C:21]3([C:24]([NH:25][C:26]4[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=4)=[O:33])[CH2:23][CH2:22]3)=[O:20])=[CH:17][C:2]=2[F:1])[CH:10]=[CH:9][N:8]=1

참가 물질

6

반응물 4

HCID 962Water2회HCID 1049Pyridine2회HCID 102317Bis(trifluoroacetoxy)iodobenzene2회HCID 595969854-(2-Fluoro-4-{[1-(4-fluorophenylcarbamoyl)cyclopropanecarbonyl]amino}phenoxy)pyridine-2-carboxamide

생성물 1

HCID 59596906N-{4-[(2-Aminopyridin-4-yl)oxy]-3-fluorophenyl}-N'-(4-fluorophenyl)cyclopropane-1,1-dicarboxamide수율 64%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

4-(2-Fluoro-4-{[1-(4-fluorophenylcarbamoyl)cyclopropanecarbonyl]amino}phenoxy)pyridine-2-carboxamide (4.81 g) was dissolved in N,N-dimethylformamide (50 ml) under a nitrogen atmosphere, and water (0.5 ml), [bis(trifluoroacetoxy)iodo]benzene (5.17 g) and pyridine (2.57 ml) were added in this order at room temperature, followed by stirring overnight. Water (0.5 ml), [bis(trifluoroacetoxy)iodo]benzene (5.17 g) and pyridine (2.57 ml) were added in this order at room temperature, followed by further stirring for 1 hr. The reaction mixture was partitioned between ethyl acetate (200 ml) and water (100 ml). The organic layer was separated, washed with brine, and dried over anhydrous sodium sulfate. The solvent was concentrated under reduced pressure and the residue was purified by silica gel column chromatography (Fuji Silysia NH, eluent; ethyl acetate). Fractions containing the target compound were concentrated under reduced pressure and the residue was dried under reduced pressure to provide the titled compound as pale brown foam (2.878 g, 64%).

후처리

  1. stirringby further stirring for 1 hr
  2. customThe reaction mixture was partitioned between ethyl acetate (200 ml) and water (100 ml)
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationThe solvent was concentrated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (Fuji Silysia NH, eluent; ethyl acetate)
  8. additionFractions containing the target compound
  9. concentrationwere concentrated under reduced pressure
  10. customthe residue was dried under reduced pressure

출처 및 근거

ORD 기록
ord-4ca7671ee11f462daf5ce47cc41ebd3b
출처 데이터셋
uspto-grants-2010_12
특허 번호
US07855290B2

반응 노트

불러오는 중…