Hydrochloric Acid → 8-(1-(3-chloro-2-fluorophenylamino) ethyl)-2-morpholino-4-oxo-4H-chromene-6-carboxylic acid

HRID 572730Notes

Reaction equation

HRID 572730 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[C:5]([F:34])=[C:6]([NH:10][CH:11]([C:13]2[CH:14]=[C:15]([C:30]([O:32]C)=[O:31])[CH:16]=[C:17]3[C:22]=2[O:21][C:20]([N:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)=[CH:19][C:18]3=[O:29])[CH3:12])[CH:7]=[CH:8][CH:9]=1.C1COCC1.Cl>CO>[Cl:3][C:4]1[C:5]([F:34])=[C:6]([NH:10][CH:11]([C:13]2[CH:14]=[C:15]([C:30]([OH:32])=[O:31])[CH:16]=[C:17]3[C:22]=2[O:21][C:20]([N:23]2[CH2:24][CH2:25][O:26][CH2:27][CH2:28]2)=[CH:19][C:18]3=[O:29])[CH3:12])[CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 58234989methyl 8-(1-(3-chloro-2-fluorophenylamino)ethyl)-2-morpholino-4-oxo-4H-chromene-6-carboxylate

Product 1

HCID 582350028-(1-(3-chloro-2-fluorophenylamino) ethyl)-2-morpholino-4-oxo-4H-chromene-6-carboxylic acidYield 89%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium hydroxide (0.217 mL, 0.43 mmol) was added to a stirred solution of methyl 8-(1-(3-chloro-2-fluorophenylamino)ethyl)-2-morpholino-4-oxo-4H-chromene-6-carboxylate (200 mg, 0.43 mmol) dissolved in MeOH (2 mL). The resulting solution was stirred at room temperature for 16 hrs. THF was added and the resulting solution was stirred at 50° C. for 8 hrs. The pH was adjusted to 3 with HCl 2N, the solvent was removed under vacuum and the residue diluted with H2O. The solid was collected by filtration, washed with water and dried to give 8-(1-(3-chloro-2-fluorophenylamino)ethyl)-2-morpholino-4-oxo-4H-chromene-6-carboxylic acid (171 mg, 88%) as a white solid. Mass Spectrum: M+H+ 447.

Workup

  1. stirringthe resulting solution was stirred at 50° C. for 8 hrs
  2. customthe solvent was removed under vacuum
  3. additionthe residue diluted with H2O
  4. filtrationThe solid was collected by filtration
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-a7d2775277194a59b52dc722084e00f4
Source dataset
uspto-grants-2015_05
Patent number
US09029374B2

Reaction notes

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