Methanesulfonic Acid → 2-(3,5-Dichlorophenyl)-tetrahydro-imidazo[1,5-a]pyrazine-1,3-dione

HRID 49977

Reaction equation

HRID 49977 reaction equation
CS(O)(=O)=O.C(OC([N:13]1[CH2:18][CH2:17][N:16]2[C:19](=[O:31])[N:20]([C:23]3[CH:28]=[C:27]([Cl:29])[CH:26]=[C:25]([Cl:30])[CH:24]=3)[C:21](=[O:22])[CH:15]2[CH2:14]1)=O)(C)(C)C>C(Cl)Cl>[Cl:29][C:27]1[CH:28]=[C:23]([N:20]2[C:21](=[O:22])[CH:15]3[CH2:14][NH:13][CH2:18][CH2:17][N:16]3[C:19]2=[O:31])[CH:24]=[C:25]([Cl:30])[CH:26]=1

Participants

4

Reactant 2

HCID 6395Methanesulfonic AcidHCID 224792022-(3,5-Dichlorophenyl)-1,3-dioxo-hexahydro-imidazo[1,5-a]pyrazine-7-carboxylic Acid Tert-Butyl Ester

Product 1

HCID 213010012-(3,5-Dichlorophenyl)-tetrahydro-imidazo[1,5-a]pyrazine-1,3-dioneYield 86.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methanesulfonic acid (2.1 mL, 32.7 mmol) was added to an ice-cold solution of 2-(3,5-Dichlorophenyl)-1,3-dioxo-hexahydro-imidazo[1,5-a]pyrazine-7-carboxylic acid tert-butyl ester (2.62 g, 6.54 mmol, Prep. 18) in methylene chloride (50 mL). After 1 h at RT, TEA (5 mL, 36 mmol) was added. The reaction mixture was washed twice with water, dried over sodium sulfate and concentrated in vacuo to yield the above compound (1.7 g) as a white solid. Mp=134° C. (crystallized from diethyl ether).

Workup

  1. washThe reaction mixture was washed twice with water
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8a0b8336ae4c49f1b62ba2ba780e4fce
Source dataset
uspto-grants-2004_03
Patent number
US06710064B2

Linked notes

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