1,1-Dimethylethyl 4-({[(2-fluoro-6-iodo-4-methylphenyl)amino]-carbonyl}amino)-1-piperidinecarboxylate → 1,1-Dimethylethyl 4-(4-fluoro-6-methyl-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)-1-piperidinecarboxylate

HRID 2061466노트

반응식

HRID 2061466 반응식
[F:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4](I)[C:3]=1[NH:10][C:11]([NH:13][CH:14]1[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]1)=[O:12]>[Cl-].[Cl-].C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].[Pd+2].O1CCOCC1>[F:1][C:2]1[C:3]2[NH:10][C:11](=[O:12])[N:13]([CH:14]3[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]3)[C:4]=2[CH:5]=[C:6]([CH3:8])[CH:7]=1

참가 물질

4

반응물 1

HCID 596832811,1-Dimethylethyl 4-({[(2-fluoro-6-iodo-4-methylphenyl)amino]-carbonyl}amino)-1-piperidinecarboxylate

생성물 1

HCID 596832531,1-Dimethylethyl 4-(4-fluoro-6-methyl-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)-1-piperidinecarboxylate

시약·촉매·용매 2

HCID 178478645Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 312751,4-Dioxane용매

반응 조건

온도
80 °C

실험 절차

Under an argon atmosphere, a mixture of 1,4-dioxane (3 ml), palladium 1,1′-bis(diphenylphosphino)ferrocene dichloride (10% mol, 0.0623 mmol, ˜x50 mg), NatBuO (2 eq., 1.26 mmol, 121 mg), were sonicated for 10 minutes at room temperature and 1,1-dimethylethyl 4-({[(2-fluoro-6-iodo-4-methylphenyl)amino]carbonyl}amino)-1-piperidine-carboxylate (D3) (1 eq., 0.623 mmol, 300 mg) was added at room temperature and the mixture was refluxed at 80° C. for one overnight. The reaction mixture was cooled to room temperature, poured onto NH4Cl (saturated solution) and the aqueous solution obtained was extracted with ethyl acetate repeatedly; the organics were combined, dried over Na2SO4, filtered and the solvent was evaporated to afford the crude compound (250 mg) that was purified by MDAP to yield the title compound, 30 mg, 11%.

후처리

  1. customwere sonicated for 10 minutes at room temperature
  2. temperatureThe reaction mixture was cooled to room temperature
  3. additionpoured onto NH4Cl (saturated solution)
  4. customthe aqueous solution obtained
  5. extractionwas extracted with ethyl acetate repeatedly
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. customthe solvent was evaporated
  9. customto afford the crude compound (250 mg) that
  10. customwas purified by MDAP

출처 및 근거

ORD 기록
ord-824456d63d3e48e6a910313350702a1c
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08283364B2

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