Methyl iodide → 6-[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

HRID 1081317Notes

Reaction equation

HRID 1081317 reaction equation
[F:1][C:2]([F:38])([F:37])[C:3]1[CH:4]=[C:5]([CH:30]=[C:31]([C:33]([F:36])([F:35])[F:34])[CH:32]=1)[CH2:6][N:7]([CH3:29])[C:8]([C:10]1[N:19]([CH3:20])[C:18](=[O:21])[C:13]2=[N:14][CH:15]=[CH:16][CH:17]=[C:12]2[C:11]=1[C:22]1[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=1)=[O:9].[I:39][CH3:40]>O1CCOCC1>[I-:39].[F:38][C:2]([F:1])([F:37])[C:3]1[CH:4]=[C:5]([CH:30]=[C:31]([C:33]([F:34])([F:36])[F:35])[CH:32]=1)[CH2:6][N:7]([CH3:29])[C:8]([C:10]1[N:19]([CH3:20])[C:18](=[O:21])[C:13]2=[N+:14]([CH3:40])[CH:15]=[CH:16][CH:17]=[C:12]2[C:11]=1[C:22]1[CH:23]=[CH:24][C:25]([F:28])=[CH:26][CH:27]=1)=[O:9]

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 98718915-(4-Fluoro-phenyl)-7-methyl-8-oxo-7,8-dihydro-[1,7]naphthyridine-6-carboxylic acid (3,5-bis-trifluoromethyl-benzyl)-methyl-amide

Product 1

HCID 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

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of N-[3,5-bis(trifluoromethyl)benzyl]-5-(4-fluorophenyl)-7,8-dihydro-N, 7-dimethyl-8-oxo-6pyrido[3,4-b]pyridinecarboxamide (Example 1) (175 mg), iodomethane (3 ml) and dioxane (3 ml) was heated for 16 hours under reflux. The solvent was distilled off to leave the above-titled compound as yellow crystals (200 mg), m.p.184°-185° C. (decomp.) (recrystallized from dioxane-ethyl acetate).

Workup

  1. temperaturewas heated for 16 hours
  2. temperatureunder reflux
  3. distillationThe solvent was distilled off
  4. customto leave
  5. customthe above-titled compound as yellow crystals (200 mg), m.p.184°-185° C. (decomp.) (recrystallized from dioxane-ethyl acetate)

Sources & evidence

ORD record
ord-9f4e30010ff44cb8b081c9a31566a902
Source dataset
uspto-grants-1996_12
Patent number
US05585385

Reaction notes

Loading…