Water → HCID 57814390, compound

HRID 1677668Notes

Reaction equation

HRID 1677668 reaction equation
[OH:1][C:2]1([C:11]2[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[CH:13][CH:12]=2)[CH2:7][CH2:6][CH2:5][N:4]2[CH:8]=[N:9][CH:10]=[C:3]12.[H-].[Na+].[CH3:21]I.O>O1CCCC1.CN(C)C=O>[CH3:21][O:1][C:2]1([C:11]2[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[CH:13][CH:12]=2)[CH2:7][CH2:6][CH2:5][N:4]2[CH:8]=[N:9][CH:10]=[C:3]12

Participants

7

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 57814377HCID 57814377, compound

Product 1

HCID 57814390HCID 57814390, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
20 °C

Procedure

A suspension of 0.63 mmol of 4-(8-hydroxyl-5,6,7,8-tetrahydroimidazo[1,5-a]pyridin-8-yl)-benzonitrile (Example 19) in 2 ml of tetrahydrofuran is added at 0° C. to a suspension of 0.76 mmol of sodium hydride (60% dispersion in paraffin) in 1 ml of tetrahydrofuran. The reaction mixture is subsequently stirred at 20° C. for 30 minutes and then cooled again to 0° C. A solution of 0.63 mmol of methyl iodide in 3 ml of N,N-dimethylformamide is added dropwise and the reaction mixture is subsequently stirred at room temperature for 16 hours. The reaction mixture is poured into water and extracted with tertbutyl methyl ether (3×). The combined organic phases are dried over sodium sulphate and evaporated. The residue is digested with diethyl ether and the solid is isolated by filtration and dried. The title compound is obtained as a white solid. Rf=0.14 (toluene/methanol 85:15), Rt=4.92 (Gradient I).

Workup

  1. temperaturecooled again to 0° C
  2. stirringthe reaction mixture is subsequently stirred at room temperature for 16 hours
  3. extractionextracted with tertbutyl methyl ether (3×)
  4. dry with materialThe combined organic phases are dried over sodium sulphate
  5. customevaporated
  6. customthe solid is isolated by filtration
  7. customdried

Sources & evidence

ORD record
ord-1c52a04e09a448b2a783dd303a09b846
Source dataset
uspto-grants-2011_08
Patent number
US08008334B2

Reaction notes

Loading…