Cesium carbonate → HCID 10276608, compound

HRID 1822831Notes

Reaction equation

HRID 1822831 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([OH:14])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:15]([NH2:17])=[O:16].[CH2:18]([C:20]1[CH:26]=[CH:25][CH:24]=[CH:23][C:21]=1[NH2:22])[CH3:19].[O:27]1[CH2:32][CH2:31][N:30]([CH2:33][CH2:34][CH2:35]Cl)[CH2:29][CH2:28]1.C([O-])([O-])=O.[Cs+].[Cs+]>C(O)C.C(O)(=O)C>[CH2:18]([C:20]1[CH:26]=[CH:25][CH:24]=[CH:23][C:21]=1[NH:22][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH2:35][CH2:34][CH2:33][N:30]3[CH2:31][CH2:32][O:27][CH2:28][CH2:29]3)=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:15]([NH2:17])=[O:16])[CH3:19]

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 113572-EthylanilineHCID 958344-(3-Chloropropyl)morpholineHCID 135788287HCID 135788287, compound

Product 1

HCID 10276608HCID 10276608, compoundYield 17.6%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 4-Chloro-7-hydroxy-6-methoxy-3-quinolinecarboxamide (0.056 g, 0.22 mmol), 2-ethylaniline (32 μL, 0.26 mmol) and acetic acid (10 μL) in ethanol (5 ml) was heated at reflux for four hours. The solvents were removed by reduced pressure and the residue was chromatographed on silica using methanol as eluent. The product was dissolved in DMSO (5 ml), morpholinopropylchloride (0.018 g, 0.11 mmol) and Cs2CO3 (0.090 g, 0.28 mmol) were added and the mixture was heated at 100° C. for 20 hours. After cooling the mixture was poured on water and the water phases were extracted with methylenechloride. The residue was chromatographed on silica using methylenechloride/methanol (9/1–1/1) as eluent, affording 9 mg (9% yield) of the titled compound. 1H NMR (CDCl3): δ 11.05 (1H, s); 8.96 (1H, s); 7.35 (1H, s); 7.32 (1H, dd); 7.12 (2H, m); 6.91 (1H, dd); 6.74 (1H, s); 4.22 (2H, m); 3.68 (4H, m); 3.25 (3H, s); 2.80 (2H, m); 2.52 (2H, q); 2.44 (4H, m); 2.08 (2H, m); 1.30 (3H, t).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for four hours
  3. customThe solvents were removed by reduced pressure
  4. customthe residue was chromatographed on silica
  5. dissolutionThe product was dissolved in DMSO (5 ml)
  6. temperatureAfter cooling the mixture
  7. additionwas poured on water
  8. extractionthe water phases were extracted with methylenechloride
  9. customThe residue was chromatographed on silica

Sources & evidence

ORD record
ord-ccdb380de8a54f5aa9fa432e7436af67
Source dataset
uspto-grants-2006_05
Patent number
US07037925B2

Reaction notes

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