Dimethylformamide → HCID 71664252, compound

HRID 1845885Notes

Reaction equation

HRID 1845885 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].CN(C)C=O.C(=O)([O-])[O-].[K+].[K+].[CH2:42](Br)[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1>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]([CH2:42][C:43]4[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=4)[CH2:26][CH2:25]3)[CH:23]=2)[CH:18]=1)[CH3:11]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 71621328HCID 71621328, compound

Product 1

HCID 71664252HCID 71664252, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

The product of the above mentioned Example 2 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) was added to N,N-dimethyl formamide (10 mL), and to which were added potassium carbonate (276 mg, 2 mmol) and benzyl bromide (342 mg, 2 mmol). The reaction mixture was warmed to 90° C. for 5 h. After the reaction mixture was cooled to room temperature, to which was added water. The reaction mixture was extracted with dichloromethane, the organic layer was washed with water for several times, dried over anhydrous sodium sulfate, and then 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 title compound as gray solid powder.

Workup

  1. temperatureAfter the reaction mixture was cooled to room temperature, to which
  2. extractionThe reaction mixture was extracted with dichloromethane
  3. washthe organic layer was washed with water for several times
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate was rotatedly concentrated to dryness
  7. customto yield a solid, which
  8. customwas purified via silica gel column chromatography (dichloromethane:methanol=10:1)

Sources & evidence

ORD record
ord-44d76726fb754edcb5d8607a2cea433e
Source dataset
uspto-grants-2015_02
Patent number
US08952002B2

Reaction notes

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