Water → HCID 178474841, compound

HRID 245759Notes

Reaction equation

HRID 245759 reaction equation
[Br:1][C:2]1[N:3]=[C:4]([C@H:12]2[CH2:17][CH2:16][C@H:15]([CH2:18][NH2:19])[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:27](Cl)(=[O:29])[CH3:28].O>ClCCl>[Br:1][C:2]1[N:3]=[C:4]([C@H:12]2[CH2:17][CH2:16][C@H:15]([CH2:18][NH:19][C:27](=[O:29])[CH3:28])[CH2:14][CH2:13]2)[N:5]2[CH:10]=[CH:9][N:8]=[C:7]([CH3:11])[C:6]=12

Participants

6

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 178432907HCID 178432907, compound

Product 1

HCID 178474841HCID 178474841, compoundYield 56.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To ((trans)-4-(1-bromo-8-methylimidazo[1,5-a]pyrazin-3-yl)cyclohexyl)methanamine (0.464 mmol, 150 mg) in dichloromethane (5 ml) at 0° C. were added triethylamine (0.466 mmol, 65 μl) and acetyl chloride (0.510 mmol, 36.4 μl). After stirring at room temperature for one hour water was added. The organic layer separated, dried (Na2SO4) and concentrated in vacuo to give N-(((trans)-4-(1-bromo-8-methylimidazo[1,5-a]pyrazin-3-yl)cyclohexyl)methyl)acetamide (96 mg)

Workup

  1. additionwas added
  2. customThe organic layer separated
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1fef8eca66bd487e8eb3dc00ccf10062
Source dataset
uspto-grants-2014_02
Patent number
US08658794B2

Reaction notes

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