Potassium Carbonate → HCID 69372083, compound

HRID 989309Notes

Reaction equation

HRID 989309 reaction equation
[C:1]([C:3]1[CH:4]=[N:5][C:6]2[CH:7]=[C:8]3[NH:31][CH:30]=[N:29][C:9]3=[CH:10][C:11]=2[C:12]=1[N:13]([C:16]1[CH:21]=[CH:20][C:19]([O:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[CH:18][CH:17]=1)C=O)#[N:2].C(=O)([O-])[O-].[K+].[K+]>CO>[O:22]([C:19]1[CH:20]=[CH:21][C:16]([NH:13][C:12]2[C:11]3[CH:10]=[C:9]4[N:29]=[CH:30][N:31]=[C:8]4[CH2:7][C:6]=3[N:5]=[CH:4][C:3]=2[C:1]#[N:2])=[CH:17][CH:18]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 178510286HCID 178510286, compound

Product 1

HCID 69372083HCID 69372083, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A suspension of 211.8 mg (0.52 mmol) of 7-cyano-3H-imidazo[4,5-g]quinolin-8-yl(4-phenoxyphenyl)formamide and 288.9 mg (2.09 mmol) of potassium carbonate in 15 mL of methanol is refluxed for 2.5 hours. The solution is concentrated and the residue is diluted with water followed by neutralization to pH 7-8 with acetic acid. The precipitate is collected by filtration and washed with water and dried in vacuo, giving a deep yellow solid. The solid is purified by flash chromatography (elution with a gradient of 98:2 to 90:10 methylene chloride/methanol) yields 137.4 mg (70.0%) of the final product as a yellow solid, mp>270° C.

Workup

  1. temperatureis refluxed for 2.5 hours
  2. concentrationThe solution is concentrated
  3. additionthe residue is diluted with water
  4. filtrationThe precipitate is collected by filtration
  5. washwashed with water
  6. customdried in vacuo
  7. customgiving a deep yellow solid
  8. customThe solid is purified by flash chromatography (
  9. washelution with a gradient of 98:2 to 90:10 methylene chloride/methanol)

Sources & evidence

ORD record
ord-2d85b73bf2ea46cd8cc094634531843d
Source dataset
uspto-grants-2003_10
Patent number
US06638929B2

Reaction notes

Loading…