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

HRID 457894Notes

Reaction equation

HRID 457894 reaction equation
[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

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

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]+.

Workup

  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

Sources & evidence

ORD record
ord-921614857a0048159b4cda6e65f36e6d
Source dataset
uspto-grants-2007_03
Patent number
US07189745B1

Reaction notes

Loading…