Water → HCID 178502113, compound

HRID 245761Notes

Reaction equation

HRID 245761 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:30])[O:28][CH3:29].O>ClCCl>[CH3:29][O:28][C:27](=[O:30])[NH:19][CH2:18][C@H:15]1[CH2:16][CH2:17][C@H:12]([C:4]2[N:5]3[CH:10]=[CH:9][N:8]=[C:7]([CH3:11])[C:6]3=[C:2]([Br:1])[N:3]=2)[CH2:13][CH2:14]1

Participants

6

Reactant 4

HCID 962WaterHCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 178432907HCID 178432907, compound

Product 1

HCID 178502113HCID 178502113, compoundYield 54.8%

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 (0.464 mmol, 64.7 μl) and methyl carbonochloridate (0.505 mmol, 39 μl). After stirring at room temperature for one hour water was added. The organic layer separated, dried (Na2SO4) and concentrated in vacuo to give methyl((trans)-4-(1-bromo-8-methylimidazo[1,5-a]pyrazin-3-yl)cyclohexyl)methylcarbamate (97 mg).

Workup

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

Sources & evidence

ORD record
ord-5361bae56cb24c0cb4083e6fbfc498ac
Source dataset
uspto-grants-2014_02
Patent number
US08658794B2

Reaction notes

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