Iodoethane → Trifluoroacetic acid

HRID 2079559Notes

Reaction equation

HRID 2079559 reaction equation
Cl.[CH3:2][N:3]1[C:11]2[CH:10]=[C:9]([C:12]3[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH2:20][CH:21]4[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]4)=[C:14]([C:27]([F:30])([F:29])[F:28])[CH:13]=3)[N:8]=[C:7]([C:31]#[N:32])[C:6]=2[N:5]=[CH:4]1.[CH2:33](I)[CH3:34].[C:36](=[O:39])([O-])[O-:37].[K+].[K+]>C(#N)C>[CH2:33]([N:24]1[CH2:23][CH2:22][CH:21]([CH2:20][CH2:19][O:18][C:15]2[CH:16]=[CH:17][C:12]([C:9]3[N:8]=[C:7]([C:31]#[N:32])[C:6]4[N:5]=[CH:4][N:3]([CH3:2])[C:11]=4[CH:10]=3)=[CH:13][C:14]=2[C:27]([F:29])([F:30])[F:28])[CH2:26][CH2:25]1)[CH3:34].[C:36]([OH:37])([C:27]([F:30])([F:29])[F:28])=[O:39]

Participants

6

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 67100725HCID 67100725, compound

Product 2

HCID 6422Trifluoroacetic acidHCID 25204408HCID 25204408, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1-Methyl-6-{4-[2-(piperidin-4-yl)-ethoxy]-3-(trifluoromethyl)-phenyl)-1H-imidazo[4,5-c]pyridine-4-carbonitrile hydrochloride (20 mg)7 ethyl iodide (10 mg) and potassium carbonate (20 mg) in acetonitrile (1 ml) was stirred at room temperature for 20 hours. After removal of solid by filtration, filtrate was purified by HPLC to give 6-{4-[2-(1-ethylpiperidin-4-yl)ethoxy]-3-(trifluoromethyl)phenyl}-1-methyl-1H-imidazo[4,5-c]pyridine-4-carbonitrile as TFA salt.

Workup

  1. customAfter removal of solid
  2. filtrationby filtration, filtrate
  3. customwas purified by HPLC

Sources & evidence

ORD record
ord-64049940e6024cb8b62483ea86f45792
Source dataset
uspto-grants-2011_04
Patent number
US07932251B2

Reaction notes

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