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

HRID 457894ノート

反応式

HRID 457894 の反応式
[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

参加物

7

反応物 4

HCID 8028TetrahydrofuranHCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 18440775HCID 18440775、化合物

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

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]+.

後処理

  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

出典と根拠

ORDレコード
ord-921614857a0048159b4cda6e65f36e6d
出典データセット
uspto-grants-2007_03
特許番号
US07189745B1

反応ノート

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