Morpholine → HCID 10162730, compound

HRID 1822837Notes

Reaction equation

HRID 1822837 reaction equation
[CH2:1]([C:3]1[CH:25]=[CH:24][CH:23]=[CH:22][C:4]=1[NH:5][C:6]1[C:15]2[C:10](=[CH:11][C:12]([OH:18])=[C:13]([O:16][CH3:17])[CH:14]=2)[N:9]=[CH:8][C:7]=1[C:19]([NH2:21])=[O:20])[CH3:2].Br[CH2:27][CH2:28][CH2:29][CH2:30]Cl.C([O-])([O-])=O.[Cs+].[Cs+].[NH:38]1[CH2:43][CH2:42][O:41][CH2:40][CH2:39]1>CS(C)=O.O>[CH2:1]([C:3]1[CH:25]=[CH:24][CH:23]=[CH:22][C:4]=1[NH:5][C:6]1[C:15]2[C:10](=[CH:11][C:12]([O:18][CH2:27][CH2:28][CH2:29][CH2:30][N:38]3[CH2:43][CH2:42][O:41][CH2:40][CH2:39]3)=[C:13]([O:16][CH3:17])[CH:14]=2)[N:9]=[CH:8][C:7]=1[C:19]([NH2:21])=[O:20])[CH3:2]

Participants

7

Reactant 4

HCID 8083MorpholineHCID 10796Cesium carbonateHCID 813641-Bromo-4-chlorobutaneHCID 135788285HCID 135788285, compound

Product 1

HCID 10162730HCID 10162730, compoundYield 22%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

4-(2-Ethylanilino)-7-hydroxy-6-methoxy-3-quinolinecarboxamide (0.064 g, 0.19 mmol) was dissolved in DMSO (4 ml), 1-bromo-4-chlorobutane (22 μl, 0.19 mmol) and Cs2CO3 (0.18 g, 0.55 mmol) were added and the mixture was stirred at ambient temperature for three days. The mixture was poured into water and extracted with methylenechloride. The residue was chromatographed on silica using ethylacetate/methanol (1:0–>1:1) as eluent. The resulting oil was dissolved in DME, morpholine (25 μl, 0.29 mmol) and a catalytic ammount of KI was added, mixture was heated at reflux for four days. After cooling the mixture was poured out on water and extracted with methylenechloride. The crude product was purified on preparative HPLC, affording 20 mg (22% yield) of the titled compound.

Workup

  1. extractionextracted with methylenechloride
  2. customThe residue was chromatographed on silica
  3. dissolutionThe resulting oil was dissolved in DME
  4. temperaturemixture was heated
  5. temperatureat reflux for four days
  6. temperatureAfter cooling the mixture
  7. additionwas poured out on water
  8. extractionextracted with methylenechloride
  9. customThe crude product was purified on preparative HPLC

Sources & evidence

ORD record
ord-beede8b8e78a40b480683ee5a66d1bd1
Source dataset
uspto-grants-2006_05
Patent number
US07037925B2

Reaction notes

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