Morpholine → HCID 59527408, compound

HRID 384497Notes

Reaction equation

HRID 384497 reaction equation
[CH3:1][C:2]1[C:11](=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:4][C:3]=1[CH2:13][O:14][C:15]1[CH:23]=[CH:22][C:18]([C:19]([OH:21])=O)=[C:17]([O:24][CH2:25][CH:26]2[CH2:31][CH2:30][O:29][CH2:28][CH2:27]2)[CH:16]=1.O.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.[NH:55]1[CH2:60][CH2:59][O:58][CH2:57][CH2:56]1>CN(C=O)C>[CH3:1][C:2]1[C:11](=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:4][C:3]=1[CH2:13][O:14][C:15]1[CH:23]=[CH:22][C:18]([C:19]([N:55]2[CH2:60][CH2:59][O:58][CH2:57][CH2:56]2)=[O:21])=[C:17]([O:24][CH2:25][CH:26]2[CH2:31][CH2:30][O:29][CH2:28][CH2:27]2)[CH:16]=1

Participants

6

Reactant 4

HCID 8083MorpholineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 59527532HCID 59527532, compound

Product 1

HCID 59527408HCID 59527408, compoundYield 93.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-[(3-Methyl-4-oxo-1,4-dihydroquinolin-2-yl)methoxy]-2-(tetrahydro-2H-pyran-4-ylmethoxy)benzoic acid (67 mg) and 1-hydroxybenzotriazole hydrate (25 mg) were dissolved in DMF (1.3 mL). To this solution were sequentially added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (33 mg) and morpholine (15 mg), and the mixture was stirred at room temperature for 12 hours. A saturated aqueous sodium hydrogen carbonate solution (5 mL) to the reaction mixture, followed by extraction with ethyl acetate (50 mL). The organic layer was washed sequentially with water and saturated brine, and then dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: chloroform/methanol=15/1) to obtain 3-methyl-2-{[4-(morpholin-4-ylcarbonyl)-3-(tetrahydro-2H-pyran-4-ylmethoxy)phenoxy]methyl}quinolin-4(1H)-one (73 mg).

Workup

  1. extractionA saturated aqueous sodium hydrogen carbonate solution (5 mL) to the reaction mixture, followed by extraction with ethyl acetate (50 mL)
  2. washThe organic layer was washed sequentially with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (eluent: chloroform/methanol=15/1)

Sources & evidence

ORD record
ord-1abf442505d14221860262fef361917b
Source dataset
uspto-grants-2013_02
Patent number
US08367702B2

Reaction notes

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