Acetic Acid → HCID 67364904, compound

HRID 245700Notes

Reaction equation

HRID 245700 reaction equation
[CH3:1][C:2]1[C:3]2[N:4]([C:8]([CH:11]3[CH2:16][CH2:15][N:14]([CH:17]4[CH2:22][CH2:21][O:20][CH2:19][CH2:18]4)[CH2:13][CH2:12]3)=[N:9][CH:10]=2)[CH:5]=[CH:6][N:7]=1.C(O)(=O)C.[Br:27]Br.O>ClCCl>[Br:27][C:10]1[N:9]=[C:8]([CH:11]2[CH2:12][CH2:13][N:14]([CH:17]3[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)[CH2:15][CH2:16]2)[N:4]2[CH:5]=[CH:6][N:7]=[C:2]([CH3:1])[C:3]=12

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 24408BromineHCID 67363917HCID 67363917, compound

Product 1

HCID 67364904HCID 67364904, compoundYield 76.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

8-Methyl-3-(1-(tetrahydro-2H-pyran-4-yl)piperidin-4-yl)imidazo[1,5-a]pyrazine (0.303 mmol, 91 mg) was dissolved in dichloromethane (2 ml) and acetic acid (30.3 mmol, 1.734 ml). With stirring, bromine (0.303 mmol, 0.016 ml) in dichloromethane (0.2 mL) was added. After stirring at room temperature for one hour water was added and the mixture concentrated in vacuo. To the residue was added saturated aqueous sodium hydrogencarbonate and the mixture extracted twice with dichloromethane/methanol. The combined organic layers were concentrated in vacuo to yield 1-bromo-8-methyl-3-(1-(tetrahydro-2H-pyran-4-yl)piperidin-4-yl)imidazo[1,5-a]pyrazine (88 mg).

Workup

  1. additionwas added
  2. concentrationthe mixture concentrated in vacuo
  3. additionTo the residue was added saturated aqueous sodium hydrogencarbonate
  4. extractionthe mixture extracted twice with dichloromethane/methanol
  5. concentrationThe combined organic layers were concentrated in vacuo

Sources & evidence

ORD record
ord-016a2e331d984ae4b7036b35e84df6ed
Source dataset
uspto-grants-2014_02
Patent number
US08658794B2

Reaction notes

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