Hydrochloric Acid → HCID 86717890, compound

HRID 1624085Notes

Reaction equation

HRID 1624085 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.O1CCCC1>[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 g of ethyl 8-[(2,6-difluorobenzyl)oxy]imidazo[1,2-a]pyridine-3-carboxylate (Example 30A, 3 mmol, 1 equivalent) was initially charged in 60 ml of methanol/tetrahydrofuran (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 hydrochloric acid. The organic solvents were removed on a rotary evaporator, water was added to the precipitated product and the product was filtered off. The filter cake was 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 off
  5. washThe filter cake was washed with water
  6. customdried under high vacuum

Sources & evidence

ORD record
ord-7514701f7c0f4b618d3736d089d43414
Source dataset
uspto-grants-2014_07
Patent number
US08778964B2

Reaction notes

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