Hydrochloric Acid → 8-Hydroxy-5-(6-methyl-1,1-dioxido-1,2,6-thiadiazinan-2-yl)-1,6-naphthyridine-7-carboxylic acid

HRID 2252824Notes

Reaction equation

HRID 2252824 reaction equation
[OH-].[Na+].[OH:3][C:4]1[C:5]([C:23]([O:25]C)=[O:24])=[N:6][C:7]([N:14]2[CH2:19][CH2:18][CH2:17][N:16]([CH3:20])[S:15]2(=[O:22])=[O:21])=[C:8]2[C:13]=1[N:12]=[CH:11][CH:10]=[CH:9]2.Cl>O1CCOCC1.O>[OH:3][C:4]1[C:5]([C:23]([OH:25])=[O:24])=[N:6][C:7]([N:14]2[CH2:19][CH2:18][CH2:17][N:16]([CH3:20])[S:15]2(=[O:22])=[O:21])=[C:8]2[C:13]=1[N:12]=[CH:11][CH:10]=[CH:9]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 59645249Methyl 8-hydroxy-5-(6-methyl-1,1-dioxido-1,2,6-thiadiazinan-2-yl)-1,6-naphthyridine-7-carboxylate

Product 1

HCID 596452528-Hydroxy-5-(6-methyl-1,1-dioxido-1,2,6-thiadiazinan-2-yl)-1,6-naphthyridine-7-carboxylic acid

Reagents, catalysts & solvents 1

HCID 218864351,4-Dioxane--water (1/1)Solvent

Conditions

Temperature
55 °C

Procedure

Sodium hydroxide (3.85 mL, 3.85 mmol, 1N solution) was added to a suspension of methyl 8-hydroxy-5-(6-methyl-1,1-dioxido-1,2,6-thiadiazinan-2-yl)-1,6-naphthyridine-7-carboxylate (452 mg, 1.28 mmol) in a 2:1 solution of dioxane/water (10 mL) and the resulting mixture was heated overnight at 55° C. overnight. The opaque solution was acidified to a pH=7 using 1N HCl solution. The reaction was cooled and the solids that had precipitated out of solution were collected by vacuum filtration to give the desired product as an off-white solid.

Workup

  1. temperatureThe reaction was cooled
  2. customthe solids that had precipitated out of solution
  3. filtrationwere collected by vacuum filtration

Sources & evidence

ORD record
ord-d5b4d710042649ae963a93acfea12b6d
Source dataset
uspto-grants-2008_01
Patent number
US07323460B2

Reaction notes

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