Hydrochloric Acid → HCID 86717941, compound

HRID 2275869Notes

Reaction equation

HRID 2275869 reaction equation
[OH-].[Li+].[F:3][C:4]1[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[C:5]=1[CH2:6][O:7][C:8]1[C:9]2[N:10]([C:15]([C:19]([O:21]CC)=[O:20])=[C:16]([CH3:18])[N:17]=2)[CH:11]=[CH:12][C:13]=1[F:14].Cl>C1COCC1.C(O)C>[F:3][C:4]1[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[C:5]=1[CH2:6][O:7][C:8]1[C:9]2[N:10]([C:15]([C:19]([OH:21])=[O:20])=[C:16]([CH3:18])[N:17]=2)[CH:11]=[CH:12][C:13]=1[F:14]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium Hydroxide2×HCID 86717940HCID 86717940, compound

Product 1

HCID 86717941HCID 86717941, compound

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

1.14 ml (1.14 mmol) of 1 N lithium hydroxide solution were added to 365 mg (0.76 mmol; purity about 76%) of ethyl 8-[(2,6-difluorobenzyl)oxy]-7-fluoro-2-methylimidazo[1,2-a]pyridine-3-carboxylate Example 269A in 16.6 ml of THF/ethanol (5/1), and the mixture was stirred at RT overnight. Another 2.67 ml (2.67 mmol) of 1 N lithium hydroxide solution were added and the mixture was stirred at RT overnight. Under reduced pressure, the reaction mixture was freed from organic solvent, and the aqueous phase was acidified to pH 4 with 6 N hydrochloric acid whilst cooling with ice water. The solid formed was filtered off and dried under high vacuum. This gave 236 mg of the target compound (87% of theory, purity 94%).

Workup

  1. stirringthe mixture was stirred at RT overnight
  2. customThe solid formed
  3. filtrationwas filtered off
  4. customdried under high vacuum

Sources & evidence

ORD record
ord-a06cc45f8d7548078531d0241460522d
Source dataset
uspto-grants-2015_09
Patent number
US09126998B2

Reaction notes

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