Hydrochloric Acid → 5-(3-Acetyl phenyl)-2-amino-5-[4-(difluoromethoxy)phenyl]-3-methyl-3,5-dihydro-4H-imidazol-4-one

HRID 30587

반응식

HRID 30587 반응식
[NH2:1][C:2]1[N:6]([CH3:7])[C:5](=[O:8])[C:4]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21](Br)[CH:20]=2)([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH:16]([F:18])[F:17])=[CH:11][CH:10]=2)[N:3]=1.C1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C([O-])([O-])=O.[K+].[K+].[CH2:61]([O:65]C=C)[CH2:62]CC.Cl>CN(C=O)C.O.O.CC([O-])=O.CC([O-])=O.[Pd+2]>[C:61]([C:21]1[CH:20]=[C:19]([C:4]2([C:9]3[CH:10]=[CH:11][C:12]([O:15][CH:16]([F:18])[F:17])=[CH:13][CH:14]=3)[N:3]=[C:2]([NH2:1])[N:6]([CH3:7])[C:5]2=[O:8])[CH:24]=[CH:23][CH:22]=1)(=[O:65])[CH3:62]

참가 물질

9

반응물 5

HCID 313Hydrochloric AcidHCID 8108Butyl vinyl etherHCID 11430Potassium Carbonate2회HCID 812191,3-Bis(diphenylphosphino)propaneHCID 597903072-amino-4-(3-bromophenyl)-4-(4-(difluoromethoxy)phenyl)-1-methyl-1H-imidazol-5(4H)-one

생성물 1

HCID 161129625-(3-Acetyl phenyl)-2-amino-5-[4-(difluoromethoxy)phenyl]-3-methyl-3,5-dihydro-4H-imidazol-4-one수율 88%

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 962Water용매HCID 21962138N,N-Dimethylformamide--water (1/1)용매

반응 조건

온도
120 °C

실험 절차

A mixture of 2-amino-5-(3-bromophenyl)-5-[4-(difluoromethoxy)phenyl]-3-methyl-3,5-dihydro-4H-imidazol-4-one (1.50 g, 3.66mmol), 1,3-bis(diphenylphosphino)propane (DPPP) (0.377 g, 0.915 mmol), K2CO3 (0.606 g, 4.39 mmol), Pd(OAc)2 (82 mg, 0.37 mmol) and n-butylvinylether (1.47 g, 14.6 mmol) in DMF/water (8 ml/0.8 ml) is heated in a microwave oven for 1 h at 120° C., cooled to room temperature, treated cautiously with 15 ml of 5% HCl, stirred at room temperature for 1 h, diluted with water, basified with aqueous K2CO3 and extracted with ethyl acetate. The extracts are combined, dried over MgSO4 and concentrated in vacuo to give a residue. The residue is purified by SCX cartridge to give the title compound, 1.20 g (88% yield), identified by NMR and mass spectral analyses. 1H NMR (300 MHz,CDCl3) ppm 8.11 (t, 1 H), 7.87 (dt, 1 H), 7.72-7.80 (m, 1 H), 7.52 (d, 2 H), 7.44 (t, 1 H), 7.08 (d, 2 H), 6.49 (t, 1 H), 3.15 (s, 3 H), 2.59 (s, 3 H). MS [M+H]+ 374.1.

후처리

  1. temperaturecooled to room temperature
  2. extractionextracted with ethyl acetate
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customto give a residue
  6. customThe residue is purified by SCX cartridge

출처 및 근거

ORD 기록
ord-ebbc9e182a1f435cbacd08012234dc03
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07423158B2

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