Methyl iodide → HCID 89708462, compound

HRID 1845889Notes

Reaction equation

HRID 1845889 reaction equation
[Cl:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[C:4]([Cl:9])[C:3]=1[CH:10]([O:12][C:13]1[C:14]([NH2:30])=[N:15][CH:16]=[C:17]([C:19]2[N:20]=[N:21][N:22]([CH:24]3[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]3)[CH:23]=2)[CH:18]=1)[CH3:11].[C:31](=O)([O-])[O-].[K+].[K+].IC>CN(C)C=O>[Cl:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[C:4]([Cl:9])[C:3]=1[CH:10]([O:12][C:13]1[C:14]([NH2:30])=[N:15][CH:16]=[C:17]([C:19]2[N:20]=[N:21][N:22]([CH:24]3[CH2:29][CH2:28][N:27]([CH3:31])[CH2:26][CH2:25]3)[CH:23]=2)[CH:18]=1)[CH3:11]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 71621328HCID 71621328, compound

Product 1

HCID 89708462HCID 89708462, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)-5-(1-(piperidin-4-yl)-1H-1,2,3-triazol-4-yl)-2-aminopyridine (451 mg, 1 mmol) in the above mentioned Example 2 was added to N,N-dimethyl formamide (10 mL), potassium carbonate (276 mg, 2 mmol) and iodomethane (425.7 mg, 3 mmol) were added, and the reaction was performed overnight at room temperature. The resultant mixture was washed with water for several times, dried over anhydrous sodium sulfate, filtered, the filtrate was rotatedly concentrated to dryness to yield a solid, which was purified via silica gel column chromatography (dichloromethane/methanol=10:1) to yield the target product as white solid powder.

Workup

  1. additionwere added
  2. washThe resultant mixture was washed with water for several times
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate was rotatedly concentrated to dryness
  6. customto yield a solid, which
  7. customwas purified via silica gel column chromatography (dichloromethane/methanol=10:1)

Sources & evidence

ORD record
ord-0f92b4c7f4c7487f9c11330ac1c382a5
Source dataset
uspto-grants-2015_02
Patent number
US08952002B2

Reaction notes

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