Dimethylformamide → HCID 10269805, compound

HRID 2413947Notes

Reaction equation

HRID 2413947 reaction equation
[CH3:1][C:2]1[NH:3][C:4]([CH3:28])=[C:5]([C:23](OCC)=[O:24])[CH:6]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[C:19]([F:22])([F:21])[F:20])[C:7]=1C(OCC)=O.[H-].[Na+].[N:31]1C=NC=N[CH:32]=1.C[N:38]([CH3:41])[CH:39]=[O:40]>>[O:40]=[C:39]1[NH:38][CH:41]=[CH:1][C:2]2[NH:3][C:4]3[CH:28]=[CH:32][NH:31][C:23](=[O:24])[C:5]=3[CH:6]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[C:19]([F:22])([F:20])[F:21])[C:7]1=2

Participants

5

Reactant 4

HCID 6228Dimethylformamide3×HCID 92621,3,5-TriazineHCID 24758Sodium hydrideHCID 1680891,4-Dihydro-2,6-dimethyl-4-(2-(trifluoromethyl)phenyl)-3,5-pyridinedicarboxylic acid diethyl ester

Product 1

HCID 10269805HCID 10269805, compound

Procedure

A solution of 39.7 g (0.1 mole) diethyl 1,4-dihydro-2,6-dimethyl-4-(2-trifluoromethylphenyl)-pyridine-3,5-dicarboxylate in 250 ml dimethylformamide is added dropwise, under an atmosphere of nitrogen, to a suspension of 6.0 g (0.2 mole) sodium hydride (80% in oil) in 100 ml dry dimethylformamide. After cessation of the evolution of gas, the reaction mixture is further stirred for 10 minutes at ambient temperature and subsequently 16.2 g (0.2 mole) s-triazine in 50 ml dimethylformamide are added dropwise thereto. The reaction mixture is stirred for 16 hours at 105° C. and, after cooling, evaporated in a vacuum. The residue is taken up in 200 ml ethanol and the crystals which separate out after stirring in an ice bath for several hours are filtered off. The mother liquor contains, as by-product, the ethyl (±)-1,4,5,6-tetrahydro-2-methyl-5-oxo-4-(2-trifluoromethylphenyl)-1,6-naphthyridine-3-carboxylate already described in German Pat. No. 33 27 650. The crystals are placed into an extraction column and extracted with methanol for 24 hours. After cooling, from the methanol solution there crystallize 1,2,5,8,9,10-hexahydro-1,9-dioxo-10-(2-trifluoromethylphenyl)-pyrido[4,3-b][1,6]naphthyridine in the form of pale beige crystals; mp 350° C. (dec).

Workup

  1. stirringThe reaction mixture is stirred for 16 hours at 105° C.
  2. temperatureafter cooling
  3. customevaporated in a vacuum
  4. customthe crystals which separate out
  5. stirringafter stirring in an ice bath for several hours
  6. filtrationare filtered off
  7. extractionThe crystals are placed into an extraction column
  8. extractionextracted with methanol for 24 hours
  9. temperatureAfter cooling, from the methanol solution there crystallize 1,2,5,8,9,10-hexahydro-1,9-dioxo-10-(2-trifluoromethylphenyl)-pyrido[4,3-b][1,6]naphthyridine in the form of pale beige crystals

Sources & evidence

ORD record
ord-68d9fe2e5bb749abb164975deba23ef6
Source dataset
uspto-grants-1988_01
Patent number
US04720499

Reaction notes

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