Water → HCID 178439972, compound

HRID 1468265Notes

Reaction equation

HRID 1468265 reaction equation
Br[C:2]1[CH:7]=[CH:6][N:5]2[C:8]([CH2:14][O:15][CH:16]3[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]3)=[C:9]([CH:11]([CH3:13])[CH3:12])[N:10]=[C:4]2[CH:3]=1.C[S-:23].[Na+].O>CC(N(C)C)=O>[CH:16]1([O:15][CH2:14][C:8]2[N:5]3[CH:6]=[CH:7][C:2]([SH:23])=[CH:3][C:4]3=[N:10][C:9]=2[CH:11]([CH3:13])[CH3:12])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1

Participants

5

Reactant 3

HCID 962WaterHCID 4378561Sodium methanethiolateHCID 86710033HCID 86710033, compound

Product 1

HCID 178439972HCID 178439972, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
160 °C

Procedure

7-Bromo-3-cyclohexyloxymethyl-2-isopropylimidazo[1,2-a]pyridine (50.0 mg, 0.142 mmol) obtained in step 3 of Example 28 was dissolved in DMA (1.0 mL), and the solution was stirred at 160° C. for 30 minutes after adding sodium thiomethoxide (80.0 mg, 1.14 mmol). After adding water to the reaction mixture, the reaction mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was then evaporated under reduced pressure. The residue was purified by silica gel chromatography (chloroform/methanol=95/5) to give 3-cyclohexyloxymethyl-2-isopropylimidazo[1,2-a]pyridine-7-thiol (35.3 mg, yield 82%).

Workup

  1. extractionthe reaction mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was then evaporated under reduced pressure
  5. customThe residue was purified by silica gel chromatography (chloroform/methanol=95/5)

Sources & evidence

ORD record
ord-0f25ebb1704146a9ba0299994eab0e88
Source dataset
uspto-grants-2015_04
Patent number
US09000186B2

Reaction notes

Loading…