Hydrochloric Acid → 4-[2-(11-Ethyl-6,11-dihydro-5-methyl-6-oxo-5h-dipyrido[3,2-b:2',3'-e][1,4]diazepin-8-yl)ethoxy]-3-methylbenzoic acid

HRID 393292Notes

Reaction equation

HRID 393292 reaction equation
[CH2:1]([N:3]1[C:9]2[N:10]=[CH:11][C:12]([CH2:14][CH2:15][O:16][C:17]3[CH:26]=[CH:25][C:20]([C:21]([O:23]C)=[O:22])=[CH:19][C:18]=3[CH3:27])=[CH:13][C:8]=2[C:7](=[O:28])[N:6]([CH3:29])[C:5]2[CH:30]=[CH:31][CH:32]=[N:33][C:4]1=2)[CH3:2].[OH-].[Na+].Cl>CO.C1COCC1>[CH2:1]([N:3]1[C:9]2[N:10]=[CH:11][C:12]([CH2:14][CH2:15][O:16][C:17]3[CH:26]=[CH:25][C:20]([C:21]([OH:23])=[O:22])=[CH:19][C:18]=3[CH3:27])=[CH:13][C:8]=2[C:7](=[O:28])[N:6]([CH3:29])[C:5]2[CH:30]=[CH:31][CH:32]=[N:33][C:4]1=2)[CH3:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 22648881Methyl 4-[2-(11-ethyl-6,11-dihydro-5-methyl-6-oxo-5h-dipyrido[3,2-b:2',3'-e][1,4]diazepin-8-yl)ethoxy]-3-methylbenzoate

Product 1

HCID 30120204-[2-(11-Ethyl-6,11-dihydro-5-methyl-6-oxo-5h-dipyrido[3,2-b:2',3'-e][1,4]diazepin-8-yl)ethoxy]-3-methylbenzoic acidYield 84.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl 4-[2-(11-ethyl-6,11-dihydro-5-methyl-6-oxo-5H-dipyrido[3,2-b:2′,3′-e][1,4]diazepin-8-yl)ethoxy]-3-methylbenzoate (471 mg, 1.05 mmol) and aqueous 1 N NaOH solution (5.0 mL, 5.0 mmol) in MeOH (10 mL) and THF (5 mL) was heated to 50° C. for 5 h. Aqueous 1 N HCl solution (6 mL) was added to the cooled reaction mixture. The resulting suspension was filtered and the solid was washed with water and dried to give the title compound (382 mg, 83% yield) as a white solid.

Workup

  1. filtrationThe resulting suspension was filtered
  2. washthe solid was washed with water
  3. customdried

Sources & evidence

ORD record
ord-ebe4299a2d784b89bf6d4bd1867c5a43
Source dataset
uspto-grants-2004_10
Patent number
US06806265B2

Reaction notes

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