Lithium hydroxide, monohydrate → HCID 69067892, compound

HRID 731618Notes

Reaction equation

HRID 731618 reaction equation
C[O:2][C:3]([C:5]1[CH:10]=[CH:9][N:8]2[CH:11]=[C:12]([C:14]3[C:15]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)=[N:16][O:17][C:18]=3[CH3:19])[N:13]=[C:7]2[CH:6]=1)=[O:4].O.[OH-].[Li+]>C1COCC1.O.CO>[CH3:19][C:18]1[O:17][N:16]=[C:15]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:14]=1[C:12]1[N:13]=[C:7]2[CH:6]=[C:5]([C:3]([OH:4])=[O:2])[CH:10]=[CH:9][N:8]2[CH:11]=1

Participants

6

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 24738344HCID 24738344, compound

Product 1

HCID 69067892HCID 69067892, compoundYield 66.5%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(5-methyl-3-phenyl-isoxazol-4-yl)-imidazo[1,2-a]pyridine-7-carboxylic acid methyl ester (1.2 g, 3.6 mmol) in THF (9.9 mL), water (9.9 mL) and methanol (2.2 mL) was added lithium hydroxide monohydrate (302 mg, 7.2 mmol) and the resulting mixture stirred vigorously overnight. The mixture was then evaporated and acidified with hydrochloric acid (1 N) and then extracted with ethyl acetate. The combined organic layers were then washed with water and brine, dried over sodium sulphate and evaporated to leave a yellow solid. Purification by trituration with heptane afforded the title compound (764 mg, 66%) which was obtained as a yellow solid. MS: m/e=318.1 [M−H]−.

Workup

  1. customThe mixture was then evaporated
  2. extractionextracted with ethyl acetate
  3. washThe combined organic layers were then washed with water and brine
  4. dry with materialdried over sodium sulphate
  5. customevaporated
  6. customto leave a yellow solid
  7. customPurification by trituration with heptane

Sources & evidence

ORD record
ord-6ae776c445334763968da1299b6f35cb
Source dataset
uspto-grants-2009_09
Patent number
US07585874B2

Reaction notes

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