Sodium hydride → HCID 178478957, compound

HRID 552847Notes

Reaction equation

HRID 552847 reaction equation
[H-].[Na+].[CH:3]1([CH2:6][OH:7])[CH2:5][CH2:4]1.F[C:9]1[CH:14]=[CH:13][C:12]([C:15]2[O:19][N:18]=[C:17]([C:20]3[CH:28]=[CH:27][C:23]4[NH:24][CH:25]=[N:26][C:22]=4[CH:21]=3)[N:16]=2)=[CH:11][C:10]=1[C:29]([F:32])([F:31])[F:30].[ClH:33].O1CCOCC1>CN(C=O)C.C(Cl)(Cl)Cl.CO.O>[ClH:33].[CH:3]1([CH2:6][O:7][C:9]2[CH:14]=[CH:13][C:12]([C:15]3[O:19][N:18]=[C:17]([C:20]4[CH:28]=[CH:27][C:23]5[NH:24][CH:25]=[N:26][C:22]=5[CH:21]=4)[N:16]=3)=[CH:11][C:10]=2[C:29]([F:31])([F:32])[F:30])[CH2:5][CH2:4]1

Participants

8

Reactant 4

HCID 24758Sodium hydrideHCID 75644CyclopropanemethanolHCID 204431481,4-Dioxane hydrochlorideHCID 178505548HCID 178505548, compound

Product 1

HCID 178478957HCID 178478957, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 21584188Chloroform methanolSolvent

Procedure

To a suspension of 60% NaH (68.0 mg) in DMF was added cyclopropylmethanol (99 mg) at 0° C., followed by stirring at the same temperature for 15 min, and then 5-{5-[4-fluoro-3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl}-1H-benzimidazole (120 mg) was added thereto. The reaction mixture was stirred at room temperature for 2 hours, and then added with water. It was extracted with EtOAc, and the organic layer was concentrated. The residue was purified by silica gel column chromatography (CH3OH/chloroform=0 to 5%) to obtain an oily substance. A solution of the oily substance in chloroform-CH3OH was added with a 4M HCl/dioxane solution (0.5 ml), and concentrated to obtain 5-{5-[4-(cyclopropylmethoxy)-3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl}-1H-benzimidazole hydrochloride (20 mg) as a white solid.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 2 hours
  2. extractionIt was extracted with EtOAc
  3. concentrationthe organic layer was concentrated
  4. customThe residue was purified by silica gel column chromatography (CH3OH/chloroform=0 to 5%)
  5. customto obtain an oily substance
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-30b03708d4d64c71a2c6fa34fc6c756b
Source dataset
uspto-grants-2011_05
Patent number
US07951825B2

Reaction notes

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