3,5-Dimethylisoxazole-4-isocyanate → (+/-)-1-(3,5-Dimethyl-isoxazol-4-yl)-3-{3-fluoro-4-[2-(2-methyl-5-oxo-4-phenyl-4-propyl-4,5-dihydro-imidazol-1-yl)-acetyl]-phenyl}-urea

HRID 507406노트

반응식

HRID 507406 반응식
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:26])[CH2:9][N:10]2[C:14](=[O:15])[C:13]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)([CH2:16][CH2:17][CH3:18])[N:12]=[C:11]2[CH3:25])=[C:4]([F:27])[CH:3]=1.[N:28]([C:31]1[C:32]([CH3:37])=[N:33][O:34][C:35]=1[CH3:36])=[C:29]=[O:30]>ClCCl>[CH3:37][C:32]1[C:31]([NH:28][C:29]([NH:1][C:2]2[CH:7]=[CH:6][C:5]([C:8](=[O:26])[CH2:9][N:10]3[C:14](=[O:15])[C:13]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)([CH2:16][CH2:17][CH3:18])[N:12]=[C:11]3[CH3:25])=[C:4]([F:27])[CH:3]=2)=[O:30])=[C:35]([CH3:36])[O:34][N:33]=1

참가 물질

4

반응물 2

HCID 27362663,5-Dimethylisoxazole-4-isocyanateHCID 68463579(+/-)-3-[2-(4-Amino-2-fluoro-phenyl)-2-oxo-ethyl]-2-methyl-5-phenyl-5-propyl-3,5-dihydro-imidazol-4-one

생성물 1

HCID 25255470(+/-)-1-(3,5-Dimethyl-isoxazol-4-yl)-3-{3-fluoro-4-[2-(2-methyl-5-oxo-4-phenyl-4-propyl-4,5-dihydro-imidazol-1-yl)-acetyl]-phenyl}-urea수율 35%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A mixture of (+/−)-3-[2-(4-amino-2-fluoro-phenyl)-2-oxo-ethyl]-2-methyl-5-phenyl-5-propyl-3,5-dihydro-imidazol-4-one (116 mg, 0.25 mmol) and 4-isocyanato3,5-dimethyl-isoxazole (34.5 mg, 0.25 mmol) in 3 mL dichloromethane is stirred at room temperature for 18 hours. Subsequently the solvent is evaporated and the residue is dissolved in acetonitrile, the solution filtrated and subjected to preparative HPLC purification (Method 3) to yield (+/−)-1-(3,5-dimethyl-isoxazol-4-yl)-3-{3-fluoro-4-[2-(2-methyl-5-oxo-4-phenyl-4-propyl-4,5-dihydro-imidazol-1-yl)-acetyl]-phenyl}-urea (44 mg, 35%), LC/MS at 254 nm; [M+H] 506; Rt 2.754 min.

후처리

  1. customSubsequently the solvent is evaporated
  2. dissolutionthe residue is dissolved in acetonitrile
  3. filtrationthe solution filtrated
  4. customsubjected to preparative HPLC purification (Method 3)

출처 및 근거

ORD 기록
ord-5c78a8bb95b24c0fa2c1cbdca11c555c
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07786155B2

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