Acetic Acid → 2-Amino-7-chloro-1-ethyl-N-methyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxamide
Reaction equation
[H-].[Na+].[CH3:3][NH:4][C:5](=[O:9])[CH2:6][C:7]#[N:8].NCC[C:13]1[N:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:14]=1[C:15](F)=[O:16].[C:23](O)(=O)[CH3:24].C[N:28](C)C=O>O>[NH2:8][C:7]1[N:28]([CH2:23][CH3:24])[C:13]2[C:14]([C:15](=[O:16])[C:6]=1[C:5]([NH:4][CH3:3])=[O:9])=[CH:18][CH:19]=[C:20]([Cl:22])[N:21]=2Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Procedure
0.394 g (9.95 mmol) of 60% sodium hydride in mineral oil is added in small amounts to a solution, cooled to 0-5° C., of 0.483 g (4.93 mmol) of N-methylcyanoacetamide in 7 ml of anhydrous dimethylformamide. Stirring is continued at this temperature for 10 minutes and then a solution of 1.0 g (4.93 mmol) of 2-(aminoethyl)-6-chloronicotinic acid fluoride in 5 ml of dimethylformamide is added. The medium is stirred overnight at ambient temperature and then a further 0.197 g (4.93 mmol) of 60% sodium hydride is added in small amounts. Stirring is continued at this temperature for 10 minutes and then 0.56 ml (9.78 mmol) of acetic acid is added. 60 ml of water are subsequently added and the solid is filtered off, rinsed with water and then dried in an oven. 1.30 g of the expected product are obtained. Melting point: 283-284° C. MH+=281. Yield=94%.
Workup
- stirringThe medium is stirred overnight at ambient temperature
- stirringStirring
- waitis continued at this temperature for 10 minutes
- filtrationthe solid is filtered off
- washrinsed with water
- customdried in an oven
Sources & evidence
- ORD record
- ord-31bdc1dc1eb943a0b6244df2b7a2e724
- Source dataset
- uspto-grants-2013_11
- Patent number
- US08586602B2
Reaction notes
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