Cesium carbonate → HCID 117843135、化合物

HRID 2209073ノート

反応式

HRID 2209073 の反応式
Br[CH:2]1[CH2:5][CH2:4][CH2:3]1.[CH3:6][O:7][C:8]1[CH:9]=[C:10]([C:16]2[N:21]=[C:20]([O:22][C@@H:23]([C@H:25]3[CH2:29][NH:28][C:27](=[O:30])[CH2:26]3)[CH3:24])[C:19]3[NH:31][CH:32]=[N:33][C:18]=3[CH:17]=2)[CH:11]=[CH:12][C:13]=1[O:14][CH3:15].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.C(OCC)(=O)C>[CH:2]1([N:31]2[C:19]3[C:20]([O:22][C@@H:23]([C@H:25]4[CH2:29][NH:28][C:27](=[O:30])[CH2:26]4)[CH3:24])=[N:21][C:16]([C:10]4[CH:11]=[CH:12][C:13]([O:14][CH3:15])=[C:8]([O:7][CH3:6])[CH:9]=4)=[CH:17][C:18]=3[N:33]=[CH:32]2)[CH2:5][CH2:4][CH2:3]1

参加物

6

反応物 3

HCID 10796Cesium carbonateHCID 78110BromocyclobutaneHCID 178488441HCID 178488441、化合物

生成物 1

HCID 117843135HCID 117843135、化合物

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
80 °C

実験手順

Bromocyclobutane (18 mg, 0.137 mmol) was added to a mixture of (R)-4-((R)-1-(6-(3,4-dimethoxyphenyl)-3H-imidazo[4,5-c]pyridin-4-yloxy)ethyl)pyrrolidin-2-one 3.09 (50 mg, 0.131 mmol) and cesium carbonate (127 mg, 0.392 mmol) in 5 mL of DMF at room temperature. Reaction mixture was heated at 80° C. in a microwave reactor for one hour. Reaction mixture was taken up in ethyl acetate and washed with saturated NaHCO3 (aq) and brine. The separated organic layers were dried (MgSO4), filtered, and concentrated under reduced pressure. Residues were purified via reverse phase chromatography to yield (R)-4-((R)-1-(3-cyclobutyl-6-(3,4-dimethoxyphenyl)-3H-imidazo[4,5-c]pyridin-4-yloxy)ethyl)pyrrolidin-2-one 3.27.

後処理

  1. customReaction mixture
  2. customReaction mixture
  3. washwashed with saturated NaHCO3 (aq) and brine
  4. dry with materialThe separated organic layers were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customResidues were purified via reverse phase chromatography

出典と根拠

ORDレコード
ord-44580f456a7842dfaff71eac34a6b44e
出典データセット
uspto-grants-2016_06
特許番号
US09376441B2

反応ノート

読み込み中…