Hydrochloric Acid → HCID 86717936, compound

HRID 1844202Notes

Reaction equation

HRID 1844202 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]2[C:9]([O:10][CH2:11][C:12]3[C:17]([F:18])=[CH:16][CH:15]=[C:14]([F:19])[C:13]=3[F:20])=[CH:8][C:7]([CH3:21])=[CH:6][N:5]2[C:22]=1[C:23]([O:25]CC)=[O:24].[OH-].[Li+].Cl>C1COCC1.CO>[CH3:1][C:2]1[N:3]=[C:4]2[C:9]([O:10][CH2:11][C:12]3[C:17]([F:18])=[CH:16][CH:15]=[C:14]([F:19])[C:13]=3[F:20])=[CH:8][C:7]([CH3:21])=[CH:6][N:5]2[C:22]=1[C:23]([OH:25])=[O:24]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 86717935HCID 86717935, compound

Product 1

HCID 86717936HCID 86717936, compound

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

6.9 g (17.51 mmol) of ethyl 2,6-dimethyl-8-[(2,3,6-trifluorobenzyl)oxy]imidazo[1,2-a]pyridine-3-carboxylate from Example 145A were dissolved in 374 ml of THF/methanol (5/1), 87.5 ml (87.5 mmol) of 1 N aqueous lithium hydroxide solution were added and the mixture was stirred at 40° C. for 5 hours. After cooling, the mixture was acidified, with ice-cooling, with 6 N aqueous hydrochloric acid, and the organic solvent was then removed on a rotary evaporator. The solid formed was filtered off with suction, washed with water and then dried under high vacuum. This gave 6.7 g of the target compound (108% of theory).

Workup

  1. temperatureAfter cooling
  2. customthe organic solvent was then removed on a rotary evaporator
  3. customThe solid formed
  4. filtrationwas filtered off with suction
  5. washwashed with water
  6. customdried under high vacuum

Sources & evidence

ORD record
ord-90a0b89f169446e4a4e3ab96c4b27549
Source dataset
uspto-grants-2015_02
Patent number
US08946215B2

Reaction notes

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