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 507406ノート

反応式

HRID 507406 の反応式
[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

参加物

4

反応物 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

生成物 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}-urea収率 35%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-5c78a8bb95b24c0fa2c1cbdca11c555c
出典データセット
uspto-grants-2010_08
特許番号
US07786155B2

反応ノート

読み込み中…