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 507408노트

반응식

HRID 507408 반응식
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]

참가 물질

6

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

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온도
70 °C

실험 절차

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

후처리

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

출처 및 근거

ORD 기록
ord-f8417bb097cb46c390a001e21369ec6b
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07786155B2

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