Water → 3-(3-[(1S)-2-Methoxy-1-methylethoxy]-5-{5-[(5S)-5-methyl-4,5-dihydro-1,3-oxazol-2-yl]-1H-pyrrol-2-yl}phenoxy)-6-(methylsulfonyl)pyridazine

HRID 909651

반응식

HRID 909651 반응식
Cl[C:2]1[N:3]=[N:4][C:5]([S:8]([CH3:11])(=[O:10])=[O:9])=[CH:6][CH:7]=1.[CH3:12][O:13][CH2:14][C@H:15]([CH3:35])[O:16][C:17]1[CH:18]=[C:19]([OH:34])[CH:20]=[C:21]([C:23]2[NH:24][C:25]([C:28]3[O:29][C@@H:30]([CH3:33])[CH2:31][N:32]=3)=[CH:26][CH:27]=2)[CH:22]=1.C(=O)([O-])[O-].[Cs+].[Cs+].O>C(#N)C>[CH3:12][O:13][CH2:14][C@H:15]([CH3:35])[O:16][C:17]1[CH:18]=[C:19]([CH:20]=[C:21]([C:23]2[NH:24][C:25]([C:28]3[O:29][C@@H:30]([CH3:33])[CH2:31][N:32]=3)=[CH:26][CH:27]=2)[CH:22]=1)[O:34][C:2]1[N:3]=[N:4][C:5]([S:8]([CH3:11])(=[O:10])=[O:9])=[CH:6][CH:7]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 10796Cesium carbonateHCID 2524763-Chloro-6-(methylsulfonyl)pyridazineHCID 666811783-[(1S)-2-Methoxy-1-methylethoxy]-5-{5-[(5S)-5-methyl-4,5-dihydro-1,3-oxazol-2-yl]-1H-pyrrol-2-yl}phenol

생성물 1

HCID 666826373-(3-[(1S)-2-Methoxy-1-methylethoxy]-5-{5-[(5S)-5-methyl-4,5-dihydro-1,3-oxazol-2-yl]-1H-pyrrol-2-yl}phenoxy)-6-(methylsulfonyl)pyridazine수율 99.3%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

3-Chloro-6-(methylsulfonyl)pyridazine (41 mg, 0.27 mmol) synthesized in Example (118c) and 3-[(1S)-2-methoxy-1-methylethoxy]-5-{5-[(5S)-5-methyl-4,5-dihydro-1,3-oxazol-2-yl]-1H-pyrrol-2-yl}phenol (80 mg, 0.24 mmol) synthesized in Example (116d) were dissolved in acetonitrile (2 mL), and cesium carbonate (158 mg, 0.48 mmol) was added, followed by stirring for 1 hour under nitrogen atmosphere. To the reaction solution, water (10 mL) was added, and extraction was carried out with ethyl acetate (10 mL). The organic layer was washed with saturated brine, and subsequently dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified using silica gel column chromatography (elution solvent: methanol/methylene chloride=0%-4%) to afford the desired compound (116 mg, yield 98%) as a white solid.

후처리

  1. extractionextraction
  2. washThe organic layer was washed with saturated brine
  3. dry with materialsubsequently dried over anhydrous magnesium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe resulting residue was purified
  6. washsilica gel column chromatography (elution solvent: methanol/methylene chloride=0%-4%)

출처 및 근거

ORD 기록
ord-680e5fa77fcd4244be1fc70e409cac8f
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08017610B2

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