Morpholine → HCID 22063716, compound

HRID 1828556Notes

Reaction equation

HRID 1828556 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:15])=[C:11]([F:14])[CH:12]=3)[C:7](=[O:16])[C:6]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[C:5]2S(C)(=O)=O)[CH2:3][CH2:2]1.[NH:26]1[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1.C(N(CC)C(C)C)(C)C.CCOCC.[Mg+2].[Br-].[Br-]>O1CCCC1.C(OCC)(=O)C>[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:15])=[C:11]([F:14])[CH:12]=3)[C:7](=[O:16])[C:6]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[C:5]2[N:26]2[CH2:31][CH2:30][O:29][CH2:28][CH2:27]2)[CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 8083MorpholineHCID 81531DiisopropylethylamineHCID 9903262Magnesium bromide diethyl etherateHCID 22063687HCID 22063687, compound2×

Product 1

HCID 22063716HCID 22063716, compoundYield 62.5%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

The ethyl 1-cyclopropyl-6,7-difluoro-2-(methylsulfonyl)-4-oxo-1,4-dihydro-3-quinolinecarboxylate (140 mg, 0.377 mmol) obtained in (A) was dissolved in tetrahydrofuran (5 ml), added with morpholine (0.0395 ml, 0.452 mmol), N,N-diisopropylethylamine (0.131 ml, 0.754 mmol) and magnesium bromide diethyl etherate (389 mg, 1.51 mmol), and then the mixture was refluxed by heating for 2 hours. The reaction mixture was diluted with ethyl acetate and washed with water. The organic layer was dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was purified by preparative TLC (chloroform:methanol=100:5) to obtain the title compound (89.2 mg, 62%).

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureby heating for 2 hours
  3. washwashed with water
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe resulting residue was purified by preparative TLC (chloroform:methanol=100:5)

Sources & evidence

ORD record
ord-9838f0817b344d07bdf0c599f746e927
Source dataset
uspto-grants-2006_06
Patent number
US07056917B2

Reaction notes

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