Hydrochloric Acid → 6-[3-(5-Fluoro-pyridin-2-yl)-5-methyl-isoxazol-4-ylmethoxy]-pyridazine-3-carboxylic acid

HRID 548900Notes

Reaction equation

HRID 548900 reaction equation
C([O:3][C:4]([C:6]1[N:7]=[N:8][C:9]([O:12][CH2:13][C:14]2[C:15]([C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][N:21]=3)=[N:16][O:17][C:18]=2[CH3:19])=[CH:10][CH:11]=1)=[O:5])C.O.[OH-].[Li+].Cl>C1COCC1.O.CO>[F:26][C:23]1[CH:24]=[CH:25][C:20]([C:15]2[C:14]([CH2:13][O:12][C:9]3[N:8]=[N:7][C:6]([C:4]([OH:5])=[O:3])=[CH:11][CH:10]=3)=[C:18]([CH3:19])[O:17][N:16]=2)=[N:21][CH:22]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 426306286-[3-(5-Fluoro-pyridin-2-yl)-5-methyl-isoxazol-4-ylmethoxy]-pyridazine-3-carboxylic acid ethyl ester

Product 1

HCID 671576016-[3-(5-Fluoro-pyridin-2-yl)-5-methyl-isoxazol-4-ylmethoxy]-pyridazine-3-carboxylic acidYield 94%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-[3-(5-fluoro-pyridin-2-yl)-5-methyl-isoxazol-4-ylmethoxy]-pyridazine-3-carboxylic acid ethyl ester (379 mg, 1.1 mmol) in THF (2.6 mL), water (2.6 mL) and methanol (0.5 mL) was added lithium hydroxide monohydrate (88.8 mg, 2.1 mmol) and the resulting mixture stirred at room temperature overnight and then acidified with HCl (4 N) and extracted with ethyl acetate. The combined organic layers were then washed with water and brine, dried over sodium sulfate and evaporated to afford the title product (329 mg, 94%) which was obtained as white solid. MS: m/e=329.1 [M−H]−.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined organic layers were then washed with water and brine
  3. dry with materialdried over sodium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-e95cef4f7e5144ae9294ca1d03a5aa51
Source dataset
uspto-grants-2011_05
Patent number
US07943619B2

Reaction notes

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