Hydrochloric Acid → 8-(1-((3,5-difluorophenyl)(methyl)amino)ethyl)-2-morpholino-4-oxo-4H-chromene-6-carboxylic acid

HRID 572783Notes

Reaction equation

HRID 572783 reaction equation
[OH-].[Na+].[F:3][C:4]1[CH:5]=[C:6]([N:11]([CH3:35])[CH:12]([C:14]2[CH:15]=[C:16]([C:31]([O:33]C)=[O:32])[CH:17]=[C:18]3[C:23]=2[O:22][C:21]([N:24]2[CH2:29][CH2:28][O:27][CH2:26][CH2:25]2)=[CH:20][C:19]3=[O:30])[CH3:13])[CH:7]=[C:8]([F:10])[CH:9]=1.CO.Cl>C1COCC1.O>[F:3][C:4]1[CH:5]=[C:6]([N:11]([CH3:35])[CH:12]([C:14]2[CH:15]=[C:16]([C:31]([OH:33])=[O:32])[CH:17]=[C:18]3[C:23]=2[O:22][C:21]([N:24]2[CH2:29][CH2:28][O:27][CH2:26][CH2:25]2)=[CH:20][C:19]3=[O:30])[CH3:13])[CH:7]=[C:8]([F:10])[CH:9]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 58235022methyl 8-(1-((3,5-difluorophenyl)(methyl)amino)ethyl)-2-morpholino-4-oxo-4H-chromene-6-carboxylate

Product 1

HCID 582349758-(1-((3,5-difluorophenyl)(methyl)amino)ethyl)-2-morpholino-4-oxo-4H-chromene-6-carboxylic acidYield 86%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

2N NaOH (6.54 mL, 13.1 mmol), was added dropwise to a stirred suspension of methyl 8-(1-((3,5-difluorophenyl)(methyl)amino)ethyl)-2-morpholino-4-oxo-4H-chromene-6-carboxylate (3 g, 6.54 mmol), in THF (30 mL)/MeOH (30 mL). The resulting solution was stirred at RT overnight. The reaction mixture was diluted with water, the pH was ajusted to 3 with a 2M aq. sol. HCl. The solvents were removed and the white precipitate was collected by filtration, washed with water and dried then washed with ethyl acetate and ether to afford 8-(1-((3,5-difluorophenyl)(methyl)amino)ethyl)-2-morpholino-4-oxo-4H-chromene-6-carboxylic acid (2.5 g, 86%) which was used without further purification. Mass Spectrum: M+H+ 445.

Workup

  1. customThe solvents were removed
  2. filtrationthe white precipitate was collected by filtration
  3. washwashed with water
  4. customdried
  5. washthen washed with ethyl acetate and ether

Sources & evidence

ORD record
ord-01051a8d8575455c923f6c0802f50b4c
Source dataset
uspto-grants-2015_05
Patent number
US09029374B2

Reaction notes

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