Hydrochloric Acid → HCID 86719151, compound
Reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].C(O[C:18]([CH3:21])([CH3:20])C)(=O)CC(OC(C)(C)C)=O.[Br:22][C:23]1[N:24]=[C:25](Cl)[C:26]2[N:27](C(C)=[N:30][N:31]=2)[CH:28]=1.Cl>CN1C(=O)CCC1>[Br:22][C:23]1[N:24]=[C:18]([CH3:20])[C:21]2[N:27]([C:26]([CH3:25])=[N:31][N:30]=2)[CH:28]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 25 °C
Procedure
Caesiumcarbonate (7.25 g; 22.3 mmol) is suspended in 5 ml NMP. To this suspension di-tert-butyl malonate (4.80 g; 22.3 mmol) is added and the resulting mixture is stirred for 30 min at 25° C. Finally 6-bromo-8-chloro-3-methyl-[1,2,4]-triazolo[4,3-a]pyrazine J-1 (1.00 g; 4.04 mmol) is added and the reaction mixture is stirred for 18 h at 25° C. The reaction mixture is treated with aqueous 1 N HCl until the pH value is below 5 and then extracted with DCM. The organic layer is separated and dried over MgSO4 and is evaporated to dryness. The crude intermediate is purified using reverse phase chromatography (method prep. HPLC2). The intermediate is dissolved in 5 ml DCM and 5 ml TFA and stirred for 16 h at 40° C. The reaction mixture is evaporated and the crude product is purified using reverse phase chromatography (method prep. HPLC2).
Workup
- stirringthe reaction mixture is stirred for 18 h at 25° C
- extractionextracted with DCM
- customThe organic layer is separated
- dry with materialdried over MgSO4
- customis evaporated to dryness
- customThe crude intermediate is purified
- dissolutionThe intermediate is dissolved in 5 ml DCM
- stirring5 ml TFA and stirred for 16 h at 40° C
- customThe reaction mixture is evaporated
- customthe crude product is purified
Sources & evidence
- ORD record
- ord-11c3dfa7901241a087045c04e6fb0198
- Source dataset
- uspto-grants-2016_02
- Patent number
- US09266891B2
Reaction notes
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