Hydrochloric Acid → HCID 67362804, compound

HRID 245693Notes

Reaction equation

HRID 245693 reaction equation
[Br:1][C:2]1[N:3]=[C:4]([CH:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)[N:5]2[CH:10]=[CH:9][N:8]=[C:7]([CH3:11])[C:6]=12.C(N(CC)CC)C.C[Si]([N:29]=[C:30]=[O:31])(C)C.Cl.[OH-].[Na+]>ClCCl.O>[Br:1][C:2]1[N:3]=[C:4]([CH:12]2[CH2:17][CH2:16][N:15]([C:30]([NH2:29])=[O:31])[CH2:14][CH2:13]2)[N:5]2[CH:10]=[CH:9][N:8]=[C:7]([CH3:11])[C:6]=12

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 70696Trimethylsilyl isocyanateHCID 67363964HCID 67363964, compound

Product 1

HCID 67362804HCID 67362804, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

1-Bromo-8-methyl-3-(piperidin-4-yl)imidazo[1,5-a]pyrazine (0.169 mmol, 50 mg) was dissolved in dichloromethane (1 ml) and triethylamine (0.545 mmol, 76 μl) and trimethylsilyl isocyanate (0.186 mmol, 25.3 μl) were added at 0° C. After stirring at room temperature for one hour water and 2N hydrochloric acid was added and stirred for 15 minutes. The reaction mixture was basified with 2 N aqueous sodium hydroxide until pH=10 and extracted three times with dichloromethane. The combined organic extracts were dried (sodium sulfate) and concentrate in vacuo to afford 4-(1-bromo-8-methylimidazo[1,5-a]pyrazin-3-yl)piperidine-1-carboxamide (40 mg).

Workup

  1. additionwas added
  2. extractionextracted three times with dichloromethane
  3. dry with materialThe combined organic extracts were dried (sodium sulfate)
  4. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-b1ca26e562464c3aa40b6c00aaee3c97
Source dataset
uspto-grants-2014_02
Patent number
US08658794B2

Reaction notes

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