2-(Bromomethyl)tetrahydro-2H-pyran → HCID 11677080, compound

HRID 229857Notes

Reaction equation

HRID 229857 reaction equation
[N:1]1([NH:7][C:8]([C:10]2[N:11]=[C:12]([C:16]3[CH:21]=[CH:20][C:19]([O:22][C:23]([F:26])([F:25])[F:24])=[CH:18][CH:17]=3)[NH:13][C:14]=2[CH3:15])=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CC([O-])(C)C.[K+].Br[CH2:34][CH:35]1[CH2:40][CH2:39][CH2:38][CH2:37][O:36]1>C(#N)C.C(OC(=O)C)C.O>[N:1]1([NH:7][C:8]([C:10]2[N:11]=[C:12]([C:16]3[CH:21]=[CH:20][C:19]([O:22][C:23]([F:25])([F:26])[F:24])=[CH:18][CH:17]=3)[N:13]([CH2:34][CH:35]3[CH2:40][CH2:39][CH2:38][CH2:37][O:36]3)[C:14]=2[CH3:15])=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 1419172-(Bromomethyl)tetrahydro-2H-pyranHCID 23665647Potassium tert-butoxideHCID 69020706HCID 69020706, compound

Product 1

HCID 11677080HCID 11677080, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 22728543Water ethylacetateSolvent

Procedure

To a suspension of 100 mg of 5-methyl-2-(4-trifluoromethoxy-phenyl)-1H-imidazole-4-carboxylic acid piperidin-1-ylamide in 3 ml of acetonitrile was added 33 mg of potassium tert-butylate and the reaction mixture was stirred at room temperature for 2 minutes. After such time, 0.034 ml of 2-(bromomethyl)-tetrahydro-2H-pyran (as R3—(CH2)m—Br) was added and the reaction mixture was stirred at 100° C. for 26 hours under argon atmosphere. The reaction mixture was then diluted with ethylacetate/water, the aqueous phase removed, and the organic phase was washed with 2×H2O followed by brine, dried (MgSO4), and after filtration concentrated in vacuo and purified by column chromatography (50 g SiO2, CH2Cl2/MeOH: 24/1) to give 44 mg of the title compound as a pale yellow solid, MS (ISP) 467.2 (M+H)+.

Workup

  1. stirringthe reaction mixture was stirred at 100° C. for 26 hours under argon atmosphere
  2. customthe aqueous phase removed
  3. washthe organic phase was washed with 2×H2O
  4. dry with materialdried (MgSO4)
  5. filtrationafter filtration
  6. concentrationconcentrated in vacuo
  7. custompurified by column chromatography (50 g SiO2, CH2Cl2/MeOH: 24/1)

Sources & evidence

ORD record
ord-fdd547d440ef47ff898de7cd25c69d9c
Source dataset
uspto-grants-2009_07
Patent number
US07563910B2

Reaction notes

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