Hydrochloric Acid → HCID 86717890, compound

HRID 2275779Notes

Reaction equation

HRID 2275779 reaction equation
[F:1][C:2]1[CH:23]=[CH:22][CH:21]=[C:20]([F:24])[C:3]=1[CH2:4][O:5][C:6]1[C:7]2[N:8]([C:12]([C:15]([O:17]CC)=[O:16])=[CH:13][N:14]=2)[CH:9]=[CH:10][CH:11]=1.[OH-].[Li+].Cl>CO.C1COCC1>[F:1][C:2]1[CH:23]=[CH:22][CH:21]=[C:20]([F:24])[C:3]=1[CH2:4][O:5][C:6]1[C:7]2[N:8]([C:12]([C:15]([OH:17])=[O:16])=[CH:13][N:14]=2)[CH:9]=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 86717889HCID 86717889, compound

Product 1

HCID 86717890HCID 86717890, compound

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

1 of ethyl 8-[(2,6-difluorobenzyl)oxy]imidazo[1,2-a]pyridine-3-carboxylate (Example 27A, 3 mmol, 1 equivalent) were initially charged in 60 ml of methanol/THF (5:1), 15 ml of a 1 N aqueous lithium hydroxide solution (15 mmol, 5 equivalents) were added and the mixture was warmed to 40° C. and stirred at this temperature for 4 h. The mixture was then cooled and, with ice cooling, adjusted to pH 4 using 6 N aqueous hydrochloric acid. The organic solvents were removed on a rotary evaporator, water was added to the precipitated product and the product was filtered, washed with water and dried under high vacuum. This gave 797 mg (87% of theory) of the title compound.

Workup

  1. temperatureThe mixture was then cooled and, with ice cooling, adjusted to pH 4
  2. customThe organic solvents were removed on a rotary evaporator, water
  3. additionwas added to the precipitated product
  4. filtrationthe product was filtered
  5. washwashed with water
  6. customdried under high vacuum

Sources & evidence

ORD record
ord-b04a18e569f74e0aa757497c49fe58dc
Source dataset
uspto-grants-2015_09
Patent number
US09126998B2

Reaction notes

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