Cesium carbonate → HCID 117843135, 화합물

HRID 2209073노트

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HRID 2209073 반응식
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

참가 물질

6

반응물 3

HCID 10796Cesium carbonateHCID 78110BromocyclobutaneHCID 178488441HCID 178488441, 화합물

생성물 1

HCID 117843135HCID 117843135, 화합물

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

반응 조건

온도
80 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-44580f456a7842dfaff71eac34a6b44e
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09376441B2

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