Methanesulfonic Acid → 8a-Pyridin-2-ylmethyl-2-(2,2,2-trifluoro-ethyl)-tetrahydro-imidazo[1,5-a]pyrazine-1,3-dione

HRID 991950Notes

Reaction equation

HRID 991950 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]2[C:14](=[O:23])[N:15]([CH2:18][C:19]([F:22])([F:21])[F:20])[C:16](=[O:17])[C:10]2([CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=2)[CH2:9]1)=O)(C)(C)C.CS(O)(=O)=O.C(N(CC)CC)C>C(Cl)Cl>[N:26]1[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=1[CH2:24][C:10]12[C:16](=[O:17])[N:15]([CH2:18][C:19]([F:21])([F:22])[F:20])[C:14](=[O:23])[N:11]1[CH2:12][CH2:13][NH:8][CH2:9]2

Participants

5

Reactant 3

HCID 6395Methanesulfonic AcidHCID 8471TriethylamineHCID 113163151,3-Dioxo-8a-pridin-2-ylmethyl-2-(2,2,2-trifluoro-ethyl)-hexahydroimidazo [1,5-a]pyrazine-7-carboxylic acid tert-butyl ester

Product 1

HCID 113364048a-Pyridin-2-ylmethyl-2-(2,2,2-trifluoro-ethyl)-tetrahydro-imidazo[1,5-a]pyrazine-1,3-dioneYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1,3-dioxo-8a-pyridin-2-ylmethyl-2-(2,2,2-trifluoro-ethyl)-hexahydro-imidazo[1,5-a]pyrazine-7-carboxylic acid tert-butyl ester (prepared as described in Step 5, 1.89 g, 4.4 mmol) in CH2Cl2 (20 mL) was added MeSO3H (2.14 g, 22 mmol). The reaction mixture was stirred at room temperature for one hour. Triethylamine (2.45 g, 24.2 mmol) was added to the solution. The organic layer was washed with 100 mL of H2O, brine, dried over MgSO4, and concentrated to give a 1.4 g of the title compound as a yellow oil (97%). The oil solidified upon granulation in hexane or upon cooling.

Workup

  1. washThe organic layer was washed with 100 mL of H2O, brine
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-6d0c8b8abd1e41ddaab1f552462a2df7
Source dataset
uspto-grants-2002_10
Patent number
US06465651B2

Reaction notes

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