Cesium carbonate → HCID 178477281、化合物

HRID 724332ノート

反応式

HRID 724332 の反応式
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]

参加物

5

反応物 3

HCID 10796Cesium carbonateHCID 129052213-(Ethylsulfanyl)phenolHCID 178496463HCID 178496463、化合物

生成物 1

HCID 178477281HCID 178477281、化合物収率 38.6%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
55 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-d7b665c7e3dd44eb932dd1632f0011af
出典データセット
uspto-grants-2006_11
特許番号
US07141586B2

反応ノート

読み込み中…