Sodium Hydroxide → N-[3,5-Bis(trifluoromethyl)benzyl]-5-(4-fluorophenyl)-1,2,7,8-tetrahydro-N,1,7-trimethyl-2,8-dioxo-6-pyrido [3,4-b]pyridinecarboxamide

HRID 1081320Notes

Reaction equation

HRID 1081320 reaction equation
[I-].[F:2][C:3]([F:40])([F:39])[C:4]1[CH:5]=[C:6]([CH:32]=[C:33]([C:35]([F:38])([F:37])[F:36])[CH:34]=1)[CH2:7][N:8]([CH3:31])[C:9]([C:11]1[N:21]([CH3:22])[C:20](=[O:23])[C:14]2=[N+:15]([CH3:19])[CH:16]=[CH:17][CH:18]=[C:13]2[C:12]=1[C:24]1[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=1)=[O:10].[OH-:41].[Na+]>[Fe-3](C#N)(C#N)(C#N)(C#N)(C#N)C#N.[K+].[K+].[K+].C1COCC1>[F:40][C:3]([F:2])([F:39])[C:4]1[CH:5]=[C:6]([CH:32]=[C:33]([C:35]([F:37])([F:38])[F:36])[CH:34]=1)[CH2:7][N:8]([CH3:31])[C:9]([C:11]1[N:21]([CH3:22])[C:20](=[O:23])[C:14]2[N:15]([CH3:19])[C:16](=[O:41])[CH:17]=[CH:18][C:13]=2[C:12]=1[C:24]1[CH:25]=[CH:26][C:27]([F:30])=[CH:28][CH:29]=1)=[O:10]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 233640506-[N-[3,5-Bis(trifluoromethyl)benzyl]-N-methylamino carbonyl]-5-(4-fluorophenyl)-7,8-dihydro-1,7-dimethyl-8-oxopyrido[3,4-b]pyridinium iodide

Product 1

HCID 22355428N-[3,5-Bis(trifluoromethyl)benzyl]-5-(4-fluorophenyl)-1,2,7,8-tetrahydro-N,1,7-trimethyl-2,8-dioxo-6-pyrido [3,4-b]pyridinecarboxamide

Reagents, catalysts & solvents 2

HCID 178511488HCID 178511488, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 6-[N-[3,5-bis(trifluoromethyl)benzyl]-N-methylaminocarbonyl]-5-(4-fluorophenyl)-7,8-dihydro-1,7-dimethyl-8-oxopyrido[3,4-b]pyridinium iodide (Example 29) (100 mg), THF (3 ml), potassium ferricyanide (500 mg) and 1N-NaOH was stirred for 15 hours. The solvent was distilled off. To the residue was added ethyl acetate, and the mixture was washed with water and dried, then the solvent was distilled off. The residue was subjected to a silica-gel column chromatography (ethyl acetate) for separation and purification to afford the above-titled compound as colorless crystals (35 mg), m.p.210°-212° C. (recrystallized from ethyl acetate-isopropyl ether).

Workup

  1. distillationThe solvent was distilled off
  2. additionTo the residue was added ethyl acetate
  3. washthe mixture was washed with water
  4. customdried
  5. distillationthe solvent was distilled off
  6. customThe residue was subjected to a silica-gel column chromatography (ethyl acetate) for separation and purification
  7. customto afford
  8. customthe above-titled compound as colorless crystals (35 mg), m.p.210°-212° C. (recrystallized from ethyl acetate-isopropyl ether)

Sources & evidence

ORD record
ord-dd00fcd111ea4338ba4de17e4e8d3172
Source dataset
uspto-grants-1996_12
Patent number
US05585385

Reaction notes

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