Methyl iodide → 1-methyl-3-(3-trifluoromethyl-7,8-dihydro-5H-[1,6]naphthyridine-6-carbonyl)-3H-imidazol-1-ium iodide

HRID 406461Notes

Reaction equation

HRID 406461 reaction equation
[N:1]1([C:6]([N:8]2[CH2:17][CH2:16][C:15]3[N:14]=[CH:13][C:12]([C:18]([F:21])([F:20])[F:19])=[CH:11][C:10]=3[CH2:9]2)=[O:7])[CH:5]=[CH:4][N:3]=[CH:2]1.[CH3:22][I:23]>CC#N>[I-:23].[CH3:22][N+:3]1[CH:4]=[CH:5][N:1]([C:6]([N:8]2[CH2:17][CH2:16][C:15]3[N:14]=[CH:13][C:12]([C:18]([F:20])([F:21])[F:19])=[CH:11][C:10]=3[CH2:9]2)=[O:7])[CH:2]=1

Participants

4

Reactant 2

HCID 6328Methyl iodide2×HCID 59764813imidazol-1-yl-(3-trifluoromethyl-7,8-dihydro-5H-[1,6]naphthyridin-6-yl)-methanone

Product 1

HCID 866217201-methyl-3-(3-trifluoromethyl-7,8-dihydro-5H-[1,6]naphthyridine-6-carbonyl)-3H-imidazol-1-ium iodideYield 100%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a suspension of imidazol-1-yl-(3-trifluoromethyl-7,8-dihydro-5H-[1,6]naphthyridin-6-yl)-methanone (preparation #1) (1.28 g, 4.32 mmol) in MeCN (10 mL) was added methyl iodide (1.1 mL, 17 mmol) and the reaction mixture was stirred at ambient temperature for about 2 h. Additional methyl iodide (0.5 mL, 8 mol) was added and stirring resumed for about 16 h. The reaction mixture was concentrated in vacuo to afford 1-methyl-3-(3-trifluoromethyl-7,8-dihydro-5H-[1,6]naphthyridine-6-carbonyl)-3H-imidazol-1-ium iodide (1.89 g, 100%) as an orange solid which was used in subsequent reactions without further purification. RP-HPLC (Table 1, Method d) Rt 1.77 min; m/z: (M+H)+ 311.

Workup

  1. stirringstirring
  2. waitresumed for about 16 h
  3. concentrationThe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-4f73ae7ba8ef46f9b38d3627d9dd6313
Source dataset
uspto-grants-2014_06
Patent number
US08754107B2

Reaction notes

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