Potassium Carbonate → HCID 69372123, compound

HRID 989306Notes

Reaction equation

HRID 989306 reaction equation
[C:1]([C:3]1[CH:4]=[N:5][C:6]2[CH2:7][C:8]3[C:9]([N:28]=[CH:29][N:30]=3)=[CH:10][C:11]=2[C:12]=1[N:13]([C:16]1[CH:21]=[C:20]([O:22][CH3:23])[C:19]([O:24][CH3:25])=[C:18]([O:26][CH3:27])[CH:17]=1)C=O)#[N:2].C(=O)([O-])[O-].[K+].[K+]>CO.O.CC(O)=O>[CH3:27][O:26][C:18]1[CH:17]=[C:16]([CH:21]=[C:20]([O:22][CH3:23])[C:19]=1[O:24][CH3:25])[NH:13][C:12]1[C:11]2[CH:10]=[C:9]3[N:28]=[CH:29][N:30]=[C:8]3[CH2:7][C:6]=2[N:5]=[CH:4][C:3]=1[C:1]#[N:2]

Participants

6

Reactant 2

HCID 11430Potassium CarbonateHCID 86584081HCID 86584081, compound

Product 1

HCID 69372123HCID 69372123, compoundYield 68.5%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A suspension of 138.6 mg (0.34 mmol) of 7-cyanoimidazo[4,5-g]quinolin-8-yl(3,4,5-trimethoxyphenyl)formamide and 229.1 mg (1.66 mmol) of potassium carbonate in 10 mL of methanol is refluxed for 2 hours. After cooling, the solution is diluted with water and neutralized to pH 7 with AcOH. The precipitate is collected by filtration and washed with water, diethyl ether and ethyl acetate. After drying in vacuo, this yields a crude product. Purification of the crude product by flash chromatography (elution with 95:5 methylene chloride/methanol) yields 87.3 mg (68.5%) of the final product as a yellow solid, mp>260° C.

Workup

  1. temperatureis refluxed for 2 hours
  2. temperatureAfter cooling
  3. filtrationThe precipitate is collected by filtration
  4. washwashed with water, diethyl ether and ethyl acetate
  5. customAfter drying in vacuo
  6. customthis yields a crude product
  7. customPurification of the crude product
  8. washby flash chromatography (elution with 95:5 methylene chloride/methanol)

Sources & evidence

ORD record
ord-6f18cf59d8a74fa3bcd0d3a61e66adc6
Source dataset
uspto-grants-2003_10
Patent number
US06638929B2

Reaction notes

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