Sodium Carbonate → HCID 13506776, compound

HRID 1583443Notes

Reaction equation

HRID 1583443 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:14]([C:15]2[C:20]([F:21])=[C:19]([F:22])[C:18]([F:23])=[C:17]([F:24])[C:16]=2[F:25])[C:13]2[C:12](=[O:26])[CH2:11][NH:10][CH2:9][C:8]=2[NH:7][C:6]=1[CH3:27])=[O:4].[O:28]([CH2:35][CH2:36][CH2:37]Br)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(O)CCC>[CH3:1][O:2][C:3]([C:5]1[CH:14]([C:15]2[C:16]([F:25])=[C:17]([F:24])[C:18]([F:23])=[C:19]([F:22])[C:20]=2[F:21])[C:13]2[C:12](=[O:26])[CH2:11][N:10]([CH2:37][CH2:36][CH2:35][O:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[CH2:9][C:8]=2[NH:7][C:6]=1[CH3:27])=[O:4]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 68522Benzene, (3-bromopropoxy)-HCID 130617581,4,5,6,7,8-Hexahydro-2-methyl-5-oxo-4-(2,3,4,5,6-pentafluorophenyl)-1,7-naphthyridine-3-carboxylic Acid Methyl Ester

Product 1

HCID 13506776HCID 13506776, compoundYield 20.8%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of 10 g of 1,4,5,6,7,8-hexahydro-2-methyl-5-oxo-4-(2,3,4,5,6-pentafluorophenyl)-1,7-naphthyridine-3-carboxylic acid methyl ester, 5.6 g of 3-phenoxypropylbromide, 10 g of sodium carbonate and 175 ml of n-butanol was stirred and refluxed for 18 hours. The mixture was filtered and the filtrate was evaporated to dryness. The residue was dissolved in ethyl acetate and extracted with water. After drying over magnesium sulfate, the ethyl acetate was removed in vacuo. The residue was dissolved in methanol and saturated with hydrogen chloride. The solvent was evaporated in vacuo. The residue was dissolved in ethyl acetate and left at room temperature for 18 hours. The solid was separated and recrystallized from ethanolether. A second recrystallization from methanol afforded 2.8 g of the title compound as the hydrochloride salt, m.p. 205° C. dec.

Workup

  1. temperaturerefluxed for 18 hours
  2. filtrationThe mixture was filtered
  3. customthe filtrate was evaporated to dryness
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. extractionextracted with water
  6. dry with materialAfter drying over magnesium sulfate
  7. customthe ethyl acetate was removed in vacuo
  8. dissolutionThe residue was dissolved in methanol and saturated with hydrogen chloride
  9. customThe solvent was evaporated in vacuo
  10. dissolutionThe residue was dissolved in ethyl acetate
  11. customThe solid was separated
  12. customrecrystallized from ethanolether
  13. customA second recrystallization from methanol

Sources & evidence

ORD record
ord-f9b0f1cb49f2478bb76f7a935d2ab181
Source dataset
uspto-grants-1985_11
Patent number
US04551534

Reaction notes

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