Cesium carbonate → 6-{4-[3-((R)-2-Methyl-pyrrolidin-1-yl)-propoxy]-phenyl}-4-pyridin-2-yl-2H-pyridazin-3-one

HRID 2042640노트

반응식

HRID 2042640 반응식
[CH3:1][C@@H:2]1[CH2:6][CH2:5][CH2:4][N:3]1[CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH2:18][CH:19]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=3)[C:20](=[O:23])[NH:21][N:22]=2)=[CH:13][CH:12]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CS(C)=O>[CH3:1][C@@H:2]1[CH2:6][CH2:5][CH2:4][N:3]1[CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:12]=[CH:13][C:14]([C:17]2[CH:18]=[C:19]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=3)[C:20](=[O:23])[NH:21][N:22]=2)=[CH:15][CH:16]=1

참가 물질

4

반응물 2

HCID 10796Cesium carbonateHCID 574028506-{4-[3-((R)-2-Methyl-pyrrolidin-1-yl)-propoxy]-phenyl}-4-pyridin-2-yl-4,5-dihydro-2H-pyridazin-3-one

생성물 1

HCID 249947446-{4-[3-((R)-2-Methyl-pyrrolidin-1-yl)-propoxy]-phenyl}-4-pyridin-2-yl-2H-pyridazin-3-one

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

실험 절차

In a 10 mL round bottom flask, 6-{4-[3-((R)-2-methyl-pyrrolidin-1-yl)-propoxy]-phenyl}-4-pyridin-2-yl-4,5-dihydro-2H-pyridazin-3-one (120 mg, 0.31 mmol), and cesium carbonate (197 mg, 0.62 mmol), in dimethylsulfoxide (3 mL) was heated to 135° C. 3 h. The reaction was cooled and the slurry was partitioned between methylene chloride and water extracted three times, and then dried over MgSO4. Purification with silica gel chromatography eluting with methylene chloride/methanol (95:5), followed by HCl salt formation produced 120 mg (33%). Mp 157-161° C. MS m/z 391 (M+H).

후처리

  1. custom3 h
  2. temperatureThe reaction was cooled
  3. customthe slurry was partitioned between methylene chloride and water
  4. extractionextracted three times
  5. dry with materialdried over MgSO4
  6. customPurification with silica gel chromatography
  7. washeluting with methylene chloride/methanol (95:5)
  8. customproduced 120 mg (33%)

출처 및 근거

ORD 기록
ord-dac09adb1ca644f89a05e6bee5c08048
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08586588B2

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