Cyclohexane ethylacetate → Acetamide, N-[4-[2-(4,5-dihydro-2-methyl-5-oxo-4-phenyl-4-propyl-1H-imidazol-1-yl)acetyl]-3-fluorophenyl]-

HRID 507408ノート

反応式

HRID 507408 の反応式
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12](=[O:14])[CH3:13])=[CH:7][C:6]=1[F:15])=[O:4].[CH3:16][C:17]1[NH:21][C:20](=[O:22])[C:19]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)([CH2:23][CH2:24][CH3:25])[N:18]=1.C(=O)([O-])[O-].[K+].CC(C)=O.[K+].C1CCCCC1.C(OCC)(=O)C>C(OCC)(=O)C>[F:15][C:6]1[CH:7]=[C:8]([NH:11][C:12](=[O:14])[CH3:13])[CH:9]=[CH:10][C:5]=1[C:3](=[O:4])[CH2:2][N:21]1[C:20](=[O:22])[C:19]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)([CH2:23][CH2:24][CH3:25])[N:18]=[C:17]1[CH3:16]

参加物

6

反応物 4

HCID 21867204Cyclohexane ethylacetateHCID 68463384(+/-)-2-Methyl-5-phenyl-5-propyl-3,5-dihydro-imidazol-4-oneHCID 86346474N-[4-(2-BROMOACETYL)-3-FLUOROPHENYL]acetamideHCID 86600397Acetone potassium carbonate

生成物 1

HCID 68465160Acetamide, N-[4-[2-(4,5-dihydro-2-methyl-5-oxo-4-phenyl-4-propyl-1H-imidazol-1-yl)acetyl]-3-fluorophenyl]-収率 93.4%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

反応条件

温度
70 °C

実験手順

To a mixture of N-[4-(2-bromo-acetyl)-3-fluoro-phenyl]-acetamide (1.1 g, 2.8 mmol) and (+/−)-2-methyl-5-phenyl-5-propyl-3,5-dihydro-imidazol-4-one (541 mg, 2.5 mmol) in 5 mL acetone potassium carbonate (698 mg, 5 mmol) is added and the reaction mixture is heated at 70° C. for 10 min in the microwave oven (Biotage Initiator). The mixture is cooled to room temperature, filtered and the filtrate evaporated to yield the crude product which is subjected to flash chromatography. ISCO Companion CombiFlash, 40 g silica gel, cyclohexane/ethyl acetate-gradient, ethyl acetate 0-100% to give (+/−)-N-{3-fluoro-4-[2-(2-methyl-5-oxo-4-phenyl-4-propyl-4,5-dihydro-imidazol-1-yl)-acetyl]-phenyl}-acetamide (956 mg, 71%). LC/MS at 254 nm; [M+H] 410; Rt 2.850 min

後処理

  1. additionis added
  2. temperatureThe mixture is cooled to room temperature
  3. filtrationfiltered
  4. customthe filtrate evaporated
  5. customto yield the crude product which

出典と根拠

ORDレコード
ord-f8417bb097cb46c390a001e21369ec6b
出典データセット
uspto-grants-2010_08
特許番号
US07786155B2

反応ノート

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