Potassium Carbonate → HCID 178517382, compound
Reaction equation
CO[C:3]([C:5]1[C:10]([NH:11][C:12](=[O:22])[CH2:13][C:14]2[C:19]([Cl:20])=[CH:18][C:17]([Cl:21])=[CH:16][N:15]=2)=[N:9][CH:8]=[CH:7][N:6]=1)=[O:4].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:20][C:19]1[C:14]([C:13]2[C:12]([OH:22])=[N:11][C:10]3=[N:9][CH:8]=[CH:7][N:6]=[C:5]3[C:3]=2[OH:4])=[N:15][CH:16]=[C:17]([Cl:21])[CH:18]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
A mixture of 3-[2-(3,5-dichloro-pyrid-2-yl)-acetylamino]-pyrazine-2-carboxylic acid methyl ester (Example 1.1) (5.78 g) and potassium carbonate (2.4 g) in dry N,N-dimethylformamide (100 ml) was heated to 100° C. for 2 hours. The reaction mixture was cooled to ambient temperature and concentrated. The residue was triturated with diethyl ether and the organic phase decanted. The solid was dissolved in water and pH value adjusted to pH 5 by addition of aqueous hydrochloric acid (2M). The aqueous phase was concentrated. The residue was dissolved in methanol, the insoluble salts were removed by filtration and the filtrate was concentrated to give Compound No. A1 of Table A (4.9 g).
Workup
- temperatureThe reaction mixture was cooled to ambient temperature
- concentrationconcentrated
- customThe residue was triturated with diethyl ether
- customthe organic phase decanted
- dissolutionThe solid was dissolved in water
- additionpH value adjusted to pH 5 by addition of aqueous hydrochloric acid (2M)
- concentrationThe aqueous phase was concentrated
- dissolutionThe residue was dissolved in methanol
- customthe insoluble salts were removed by filtration
- concentrationthe filtrate was concentrated
- customto give Compound No
Sources & evidence
- ORD record
- ord-080433199fc346f981d199349f9c5cd8
- Source dataset
- uspto-grants-2014_02
- Patent number
- US08653078B2
Reaction notes
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