Cesium carbonate → HCID 178477281, 화합물

HRID 724332노트

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HRID 724332 반응식
Cl[C:2]1[N:22]=[CH:21][C:20]([F:23])=[CH:19][C:3]=1[C:4]([NH:6][C@H:7]1[CH2:12][CH2:11][C@@H:10]([NH:13][C:14](=[O:18])[CH2:15][O:16][CH3:17])[CH2:9][CH2:8]1)=[O:5].[CH2:24]([S:26][C:27]1[CH:28]=[C:29]([OH:33])[CH:30]=[CH:31][CH:32]=1)[CH3:25].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[CH2:24]([S:26][C:27]1[CH:28]=[C:29]([CH:30]=[CH:31][CH:32]=1)[O:33][C:2]1[N:22]=[CH:21][C:20]([F:23])=[CH:19][C:3]=1[C:4]([NH:6][C@H:7]1[CH2:12][CH2:11][C@@H:10]([NH:13][C:14](=[O:18])[CH2:15][O:16][CH3:17])[CH2:9][CH2:8]1)=[O:5])[CH3:25]

참가 물질

5

반응물 3

HCID 10796Cesium carbonateHCID 129052213-(Ethylsulfanyl)phenolHCID 178496463HCID 178496463, 화합물

생성물 1

HCID 178477281HCID 178477281, 화합물수율 38.6%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
55 °C

실험 절차

2-Chloro-5-fluoro-N-[cis-4-(2-methoxy-acetylamino)-cyclohexyl]-nicotinamide (110 mg, 0.32 mmol), 3-ethylsulfanyl-phenol (54 mg, 0.35 mmol) and caesium carbonate (156 mg, 0.48 mmol) were suspended in dimethylformamide (2 ml) and the reaction was heated to 55° C. and stirred at this temperature under nitrogen for 18 h. The reaction was quenched with sat. ammonium chloride solution (1 ml) and water (1 ml) and the organic phase was collected by passing the mixture through a chemelute cartridge, washing with ethyl acetate (20 ml). The solvent was removed under reduced pressure and the residue was triturated with diethylether (5 ml) to give 2-(3-ethylsulfanyl-phenoxy)-5-fluoro-N-[cis-4-(2-methoxy-acetylamino)-cyclohexyl]-nicotinamide (57 mg) as an off-white solid.

후처리

  1. customThe reaction was quenched with sat. ammonium chloride solution (1 ml) and water (1 ml)
  2. customthe organic phase was collected
  3. washwashing with ethyl acetate (20 ml)
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was triturated with diethylether (5 ml)

출처 및 근거

ORD 기록
ord-d7b665c7e3dd44eb932dd1632f0011af
출처 데이터셋
uspto-grants-2006_11
특허 번호
US07141586B2

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