Imidazole → HCID 21956471, compound

HRID 2213749Notes

Reaction equation

HRID 2213749 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[NH:12][CH2:13][CH2:14][N:15]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1)[N:8](COCC[Si](C)(C)C)[CH:7]=[C:6]([C:29]#[N:30])[C:5]2=[O:31].N1C=CN=[CH:33]1>C(O)=O>[N:15]1([CH2:14][CH2:13][N:12]2[C:11]3[C:2](=[CH:3][C:4]4[C:5](=[O:31])[C:6]([C:29]#[N:30])=[CH:7][NH:8][C:9]=4[CH:10]=3)[N:1]=[CH:33]2)[CH2:16][CH2:17][O:18][CH2:19][CH2:20]1

Participants

4

Reactant 2

HCID 795ImidazoleHCID 219563976-Amino-7-{[2-(4-morpholinyl)ethyl]amino}-4-oxo 1-{[2-(trimethylsilyl)ethoxy]methyl}-1,4-dihydro-3-quinolinecarbonitrile

Product 1

HCID 21956471HCID 21956471, compoundYield 49.4%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A mixture of 422 mg (0.95 mmol) of 6-amino-7-{[2-(4-morpholinyl)ethyl]amino}-4-oxo-1-{[2-(trimethylsilyl)ethoxy]methyl}-1,4-dihydro-3-quinolinecarbonitrile, 258.7 mg (3.80 mmol) of imidazole in 6 mL of 96% formic acid is refluxed for 6.5 hours. After cooling, the mixture is concentrated under reduced pressure and the residue is diluted with water. Undissolved solid is filtered off and washed with water. The combined filtrate and water washes are brought to pH 8 with 28% ammonium hydroxide aqueous solution. The precipitate is collected by filtration and washed with water. After drying in vacuo, this yields 190.0 mg of the crude product as a yellow solid. The crude product is purified by flash chromatography (elution with methylene chloride, then a gradient of 99:1 to 88:12 methylene chloride/methanol) to give 151.6 mg (49.3%) of the pure product as an off-white solid, mp>270° C.

Workup

  1. temperatureis refluxed for 6.5 hours
  2. temperatureAfter cooling
  3. concentrationthe mixture is concentrated under reduced pressure
  4. additionthe residue is diluted with water
  5. filtrationis filtered off
  6. washwashed with water
  7. filtrationThe precipitate is collected by filtration
  8. washwashed with water
  9. customAfter drying in vacuo
  10. customThe crude product is purified by flash chromatography (
  11. washelution with methylene chloride

Sources & evidence

ORD record
ord-02d7ed8a2bde4e2384cbbb53a026121d
Source dataset
uspto-grants-2006_09
Patent number
US07105531B2

Reaction notes

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