Water → HCID 57814390, compound

HRID 2383253Notes

Reaction equation

HRID 2383253 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 tert-butyl 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 tert-butyl 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-73fe59b9579846afbe5f7da718a4ce14
Source dataset
uspto-grants-2012_09
Patent number
US08263615B2

Reaction notes

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