Cesium carbonate → 6-(1-acetyl-4-methylpyrrolidin-2-yl)-5-(4-(methanesulfonyl)phenoxy)-2-pyridin-2-yl-1H-benzimidazole

HRID 13428

반응식

HRID 13428 반응식
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1)(=[O:4])=[O:3].C(=O)([O-])[O-].[Cs+].[Cs+].[C:18]([N:21]1[CH2:25][CH:24]([CH3:26])[CH2:23][CH:22]1[C:27]1[C:32](F)=[CH:31][C:30]([NH:34][C:35]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][N:38]=2)=O)=[C:29]([N+:43]([O-])=O)[CH:28]=1)(=[O:20])[CH3:19].O.O.[Sn](Cl)(Cl)(Cl)Cl>C(OCC)(=O)C.CN1CCCC1=O>[C:18]([N:21]1[CH2:25][CH:24]([CH3:26])[CH2:23][CH:22]1[C:27]1[C:32]([O:11][C:8]2[CH:9]=[CH:10][C:5]([S:2]([CH3:1])(=[O:3])=[O:4])=[CH:6][CH:7]=2)=[CH:31][C:30]2[N:34]=[C:35]([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][N:38]=3)[NH:43][C:29]=2[CH:28]=1)(=[O:20])[CH3:19]

참가 물질

7

반응물 4

HCID 10796Cesium carbonateHCID 1233504-(Methylsulfonyl)phenolHCID 23145536N-(4-(1-acetyl-4-methylpyrrolidin-2-yl)-5-fluoro-2-nitrophenyl)pyridine-2-carboxamideHCID 85782573Tin tetrachloride dihydrate

생성물 1

HCID 231452966-(1-acetyl-4-methylpyrrolidin-2-yl)-5-(4-(methanesulfonyl)phenoxy)-2-pyridin-2-yl-1H-benzimidazole

시약·촉매·용매 2

HCID 8857Ethyl Acetate용매HCID 13387N-methyl-2-pyrrolidone용매

반응 조건

온도
90 °C

실험 절차

13.4 mg of 4-(methanesulfonyl)phenol and 44.9 mg of cesium carbonate were added in order to an N-methyl-pyrrolidinone (2 ml) solution of 15 mg of N-(4-(1-acetyl-4-methylpyrrolidin-2-yl)-5-fluoro-2-nitrophenyl)pyridine-2-carboxamide, and the reaction liquid was stirred at 90° C. for 1 hour. 43.8 mg of tin chloride dihydrate was added to the reaction liquid, then heated up to 100° C. and stirred for 2 hours. The reaction liquid was dissolved in ethyl acetate, washed with aqueous saturated sodium bicarbonate, and dried with anhydrous sodium sulfate. The solvent was evaporated away under reduced pressure, and the resulting residue was purified through partitioning thin-layer chromatography (Kieselgel™ 60F254, Art 5744 (by Merck), chloroform/methanol=9/1) to obtain the entitled compound as a white solid.

후처리

  1. customthe reaction liquid
  2. temperatureheated up to 100° C.
  3. stirringstirred for 2 hours
  4. customThe reaction liquid
  5. washwashed with aqueous saturated sodium bicarbonate
  6. dry with materialdried with anhydrous sodium sulfate
  7. customThe solvent was evaporated away under reduced pressure
  8. customthe resulting residue was purified
  9. customthrough partitioning thin-layer chromatography (Kieselgel™ 60F254, Art 5744 (by Merck), chloroform/methanol=9/1)

출처 및 근거

ORD 기록
ord-19d0527dd4c44853b78367b7e8838554
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07728025B2

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