Dichloromethane → Methyl 4-(8-((2,4-dimethoxybenzyl)amino)-3-(2-methoxy-2-oxoethyl)imidazo[1,5-a]pyrazin-1-yl)benzoate

HRID 62455Notes

Reaction equation

HRID 62455 reaction equation
[C:1]([CH2:3][C:4]1[N:8]2[CH:9]=[CH:10][N:11]=[C:12]([NH:13][CH2:14][C:15]3[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][C:16]=3[O:23][CH3:24])[C:7]2=[C:6]([C:25]2[CH:34]=[CH:33][C:28]([C:29]([O:31][CH3:32])=[O:30])=[CH:27][CH:26]=2)[N:5]=1)#N.[C:35]([O-])(O)=[O:36].[Na+].CC(=O)[O:42]CC.C(Cl)Cl>Cl.CO>[CH3:24][O:23][C:16]1[CH:17]=[C:18]([O:21][CH3:22])[CH:19]=[CH:20][C:15]=1[CH2:14][NH:13][C:12]1[C:7]2[N:8]([C:4]([CH2:3][C:1]([O:36][CH3:35])=[O:42])=[N:5][C:6]=2[C:25]2[CH:34]=[CH:33][C:28]([C:29]([O:31][CH3:32])=[O:30])=[CH:27][CH:26]=2)[CH:9]=[CH:10][N:11]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 90303953HCID 90303953, compound

Product 1

HCID 90304136Methyl 4-(8-((2,4-dimethoxybenzyl)amino)-3-(2-methoxy-2-oxoethyl)imidazo[1,5-a]pyrazin-1-yl)benzoateYield 86%

Reagents, catalysts & solvents 1

HCID 21893726Hydrochloride methanolSolvent

Procedure

To a solution of methyl 4-(3-(cyanomethyl)-8-((2,4-dimethoxybenzyl)amino)imidazo[1,5-a]pyrazin-1-yl)benzoate (12 g, 26.2 mmol) in HCl/MeOH (150 mL) was stirred at RT for 2 hrs. After the reaction was completed, the mixture was neutralized with aq NaHCO3 and extracted with EA and water. The organic layer was dried and concentrated. The residue was purified by column chromatography on silica gel eluted with PE:EA:DCM=2:1:1 to give methyl 4-(8-((2,4-dimethoxybenzyl)amino)-3-(2-methoxy-2-oxoethyl)imidazo[1,5-a]pyrazin-1-yl)benzoate (11 g, yield 86%).

Workup

  1. extractionextracted with EA and water
  2. customThe organic layer was dried
  3. concentrationconcentrated
  4. customThe residue was purified by column chromatography on silica gel
  5. washeluted with PE

Sources & evidence

ORD record
ord-d300065d0ffc40edb5a8104e4fa61120
Source dataset
uspto-grants-2016_09
Patent number
US09446130B2

Reaction notes

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