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 sodium hydride at 60% 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 ten 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 0.197 g (4.93 mmol) of sodium hydride at 60% 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 then added and the solid is spin-filter-dried, 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
- waitis continued at this temperature for ten minutes
- stirringThe medium is stirred overnight at ambient temperature
- stirringStirring
- customthe solid is spin-filter-dried
- washrinsed with water
- customdried in an oven
Sources & evidence
- ORD record
- ord-723a7efd979b4f0f9027e56134b2c034
- Source dataset
- uspto-grants-2013_06
- Patent number
- US08470847B2
Reaction notes
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