Ethylamine → Ethyl 6-bromo-1-ethyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate

HRID 1047147Notes

Reaction equation

HRID 1047147 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:9](/[C:11](=[CH:17]/[NH:18][CH2:19][CH3:20])/[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[O:10])[C:5](Cl)=[N:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].C(N)C>C(#N)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:5](=[N:6][CH:7]=1)[N:18]([CH2:19][CH3:20])[CH:17]=[C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:9]2=[O:10]

Participants

5

Reactant 3

HCID 6341EthylamineHCID 11430Potassium CarbonateHCID 178464349HCID 178464349, compound2×

Product 1

HCID 68748009Ethyl 6-bromo-1-ethyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylateYield 79.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

The above crude compound ethyl (2Z)-2-[(5-bromo-2-chloropyridin-3-yl)carbonyl]-3-(ethylamino)prop-2-enoate (Intermediate 14, 700 mg) was suspended in acetonitrile (30 mL) and potassium carbonate (0.9 g, 6.53 mmol) and ethylamine (1 eq) were added. The mixture was heated to 80° C. for 16 h then cooled to room temperature and filtered to remove potassium carbonate. Water was added to the filtrate and the precipitated product was filtered and dried to afford 500 mg, 50% of ethyl 6-bromo-1-ethyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate.

Workup

  1. temperaturethen cooled to room temperature
  2. filtrationfiltered
  3. customto remove potassium carbonate
  4. additionWater was added to the filtrate
  5. filtrationthe precipitated product was filtered
  6. customdried

Sources & evidence

ORD record
ord-fd81e20e3d464e00a97fa31cf04c36d2
Source dataset
uspto-grants-2013_10
Patent number
US08569484B2

Reaction notes

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