Cesium carbonate → Ethyl2-[4-(4-chlorophenyl)-3-cyclopropyl-2-oxo-2,3-dihydro-1H-imidazol-1-yl]-propionate

HRID 660871노트

반응식

HRID 660871 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH:13]3[CH2:15][CH2:14]3)[C:11](=[O:16])[NH:10][CH:9]=2)=[CH:4][CH:3]=1.Br[CH:18]([CH3:24])[C:19]([O:21][CH2:22][CH3:23])=[O:20].C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:12]([CH:13]3[CH2:14][CH2:15]3)[C:11](=[O:16])[N:10]([CH:18]([CH3:24])[C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH:9]=2)=[CH:6][CH:7]=1

참가 물질

5

반응물 3

HCID 10796Cesium carbonateHCID 79040Ethyl 2-bromopropionateHCID 580118325-(4-chlorophenyl)-1-cyclopropyl-1,3-dihydro-2H-imidazol-2-one

생성물 1

HCID 58011824Ethyl2-[4-(4-chlorophenyl)-3-cyclopropyl-2-oxo-2,3-dihydro-1H-imidazol-1-yl]-propionate

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

500 mg (2.13 mmol) of 5-(4-chlorophenyl)-1-cyclopropyl-1,3-dihydro-2H-imidazol-2-one from Example 118A are dissolved in 5 ml acetonitrile and treated with 386 mg (2.13 mmol) of ethyl 2-bromopropionate and 1388 mg (4.26 mmol) of caesium carbonate. The mixture is stirred under reflux overnight. It is then concentrated, the residue is partitioned between dichloromethane and water, the organic phase is separated, and this is dried over sodium sulphate and again concentrated. The crude product is purified by flash chromatography on silica gel (eluent: first dichloromethane, then dichloromethane/methanol 200:1→100:1) and thus yields 338 mg (45% of theory) of the target compound.

후처리

  1. temperatureunder reflux overnight
  2. concentrationIt is then concentrated
  3. customthe residue is partitioned between dichloromethane and water
  4. customthe organic phase is separated
  5. dry with materialthis is dried over sodium sulphate
  6. concentrationagain concentrated
  7. customThe crude product is purified by flash chromatography on silica gel (eluent

출처 및 근거

ORD 기록
ord-303ae6f527f44bcbabf0f85dd680a8c5
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08084481B2

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