Lithium hydroxide, monohydrate → 6-(3-Methyl-5-pyridin-2-yl-3H-[1,2,3]triazol-4-ylmethoxy)-pyridazine-3-carboxylic acid

HRID 402405Notes

Reaction equation

HRID 402405 reaction equation
O.[OH-].[Li+].C([O:6][C:7]([C:9]1[N:10]=[N:11][C:12]([O:15][CH2:16][C:17]2[N:18]([CH3:28])[N:19]=[N:20][C:21]=2[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=2)=[CH:13][CH:14]=1)=[O:8])C>O.C1COCC1.CO>[CH3:28][N:18]1[C:17]([CH2:16][O:15][C:12]2[N:11]=[N:10][C:9]([C:7]([OH:8])=[O:6])=[CH:14][CH:13]=2)=[C:21]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=2)[N:20]=[N:19]1

Participants

6

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 573350986-(3-Methyl-5-pyridin-2-yl-3H-[1,2,3]triazol-4-ylmethoxy)-pyridazine-3-carboxylic acid ethyl ester

Product 1

HCID 674986856-(3-Methyl-5-pyridin-2-yl-3H-[1,2,3]triazol-4-ylmethoxy)-pyridazine-3-carboxylic acidYield 67%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of lithium hydroxide monohydrate (130 mg, 3.06 mmol) in water (5 mL) was added dropwise to a suspension of 6-(3-methyl-5-pyridin-2-yl-3H-[1,2,3]triazol-4-ylmethoxy)-pyridazine-3-carboxylic acid ethyl ester (521 mg, 1.53 mmol) in THF (5 mL) and MeOH (0.5 mL). The reaction mixture was then stirred at room temperature for 2 h. The reaction mixture was then evaporated and the residue dissolved in water, acidified with HCl (1N), and the resulting precipitate filtered off to afford the title product (320 mg, 67%) as a white solid. MS: m/e=311.2 [M−H]−.

Workup

  1. customThe reaction mixture was then evaporated
  2. dissolutionthe residue dissolved in water
  3. filtrationthe resulting precipitate filtered off

Sources & evidence

ORD record
ord-b3832445e52349db86a92d97c6f1c61b
Source dataset
uspto-grants-2014_06
Patent number
US08742097B2

Reaction notes

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