Methanol → Methyl 5-amino-2-[3-({[3-(1-cyano-1-methylethyl)phenyl]carbonyl}amino)phenoxy]benzoate

HRID 1097519노트

반응식

HRID 1097519 반응식
[C:1]([C:3]([C:6]1[CH:7]=[C:8]([C:12]([NH:14][C:15]2[CH:16]=[C:17]([CH:32]=[CH:33][CH:34]=2)[O:18][C:19]2[CH:28]=[CH:27][C:26]([N+:29]([O-])=O)=[CH:25][C:20]=2[C:21]([O:23][CH3:24])=[O:22])=[O:13])[CH:9]=[CH:10][CH:11]=1)([CH3:5])[CH3:4])#[N:2].CO.O1CCCC1>CN1CCCC1=O.[C].[Pd]>[NH2:29][C:26]1[CH:27]=[CH:28][C:19]([O:18][C:17]2[CH:32]=[CH:33][CH:34]=[C:15]([NH:14][C:12]([C:8]3[CH:9]=[CH:10][CH:11]=[C:6]([C:3]([C:1]#[N:2])([CH3:4])[CH3:5])[CH:7]=3)=[O:13])[CH:16]=2)=[C:20]([CH:25]=1)[C:21]([O:23][CH3:24])=[O:22]

참가 물질

6

반응물 3

HCID 887MethanolHCID 8028TetrahydrofuranHCID 66810330Methyl 2-[3-({[3-(1-cyano-1-methylethyl)phenyl]carbonyl}amino)phenoxy]-5-nitrobenzoate

생성물 1

HCID 66810422Methyl 5-amino-2-[3-({[3-(1-cyano-1-methylethyl)phenyl]carbonyl}amino)phenoxy]benzoate수율 92%

시약·촉매·용매 2

HCID 178418390HCID 178418390, 화합물촉매HCID 13387N-methyl-2-pyrrolidone용매

실험 절차

To a solution of methyl 2-[3-({[3-(1-cyano-1-methylethyl)phenyl]carbonyl}amino)phenoxy]-5-nitrobenzoate (4.00 g, 8.70 mmol) in 1-methylpyrrolidin-2-one (20 mL)/methanol (40 mL)/tetrahydrofuran (10 mL) was added 10% palladium-carbon (400 mg), and the mixture was stirred at room temperature for 14 hr under a hydrogen atmosphere (1 atm). Insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was diluted with ethyl acetate (200 mL), washed successively with water (100 mL×2) and saturated brine (100 mL×2), and dried over anhydrous sodium sulfate. Insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by basic silica gel column chromatography (eluate: ethyl acetate), and the obtained solution was concentrated under reduced pressure to give the title compound (3.42 g, 92%) as a pale-yellow oil.

후처리

  1. filtrationInsoluble material was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. additionThe obtained residue was diluted with ethyl acetate (200 mL)
  4. washwashed successively with water (100 mL×2) and saturated brine (100 mL×2)
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationInsoluble material was filtered off
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customThe obtained residue was purified by basic silica gel column chromatography (eluate: ethyl acetate)
  9. concentrationthe obtained solution was concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-d1b21698b7224428a125f5ee88840fe8
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08143258B2

반응 노트

불러오는 중…