Tetrahydrofuran → (2-(4-(6-methoxy-napthalen-2-yl)-5-pyridin-4-yl-1H-imidazol-2-yl)-2-methyl-propyl)-methanesulfonamide

HRID 457894노트

반응식

HRID 457894 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([C:13]1[N:14]=[C:15]([C:24]([CH3:28])([CH3:27])[CH2:25]N)[NH:16][C:17]=1[C:18]1[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=1)[CH:7]=[CH:6]2.O1CCCC1.CC[N:36](C(C)C)C(C)C.[CH3:43][S:44](Cl)(=[O:46])=[O:45]>O.ClCCl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([C:13]1[N:14]=[C:15]([C:24]([CH3:27])([CH3:28])[CH2:25][CH2:43][S:44]([NH2:36])(=[O:46])=[O:45])[NH:16][C:17]=1[C:18]1[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=1)[CH:7]=[CH:6]2

참가 물질

7

반응물 4

HCID 8028TetrahydrofuranHCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 18440775HCID 18440775, 화합물

생성물 1

HCID 18440778(2-(4-(6-methoxy-napthalen-2-yl)-5-pyridin-4-yl-1H-imidazol-2-yl)-2-methyl-propyl)-methanesulfonamide수율 44.4%

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

A solution of the product of Example 2 (15 mg, 0.04 mmol) in a 1:1 mixture of tetrahydrofuran and dichloromethane (2 mL) containing Hunig's base (9 μL, 0.05 mmol) was treated with methanesulfonyl chloride (4 μL, 0.05 mmol) and stirred at room temperature for 8 hours. The mixture was diluted with water and extracted with dichloromethane. The aqueous layer was separated and extracted with additional dichloromethane, the organic layers were combined, dried over anhydrous magnesium sulphate, filtered and concentrated at reduced pressure. The residue was chromatographed on a Gilson HPLC to give the title compound (8 mg, 44%) as a yellow solid; MS(ES) m/e. 451 [M+H]+.

후처리

  1. extractionextracted with dichloromethane
  2. customThe aqueous layer was separated
  3. extractionextracted with additional dichloromethane
  4. dry with materialdried over anhydrous magnesium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated at reduced pressure
  7. customThe residue was chromatographed on a Gilson HPLC

출처 및 근거

ORD 기록
ord-921614857a0048159b4cda6e65f36e6d
출처 데이터셋
uspto-grants-2007_03
특허 번호
US07189745B1

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