Hydrochloric Acid → 2,6-Dimethyl-8-[4,4,4-trifluoro-3-(trifluoromethyl)butoxy]imidazo[1,2-a]pyridine-3-carboxylic acid

HRID 2275858Notes

Reaction equation

HRID 2275858 reaction equation
O.O.O.O.O.O.O.O.[OH-].[Ba+2].[OH-].[CH3:12][C:13]1[N:14]=[C:15]2[C:20]([O:21][CH2:22][CH2:23][CH:24]([C:29]([F:32])([F:31])[F:30])[C:25]([F:28])([F:27])[F:26])=[CH:19][C:18]([CH3:33])=[CH:17][N:16]2[C:34]=1[C:35]([O:37]CC)=[O:36].Cl>CO.O>[CH3:12][C:13]1[N:14]=[C:15]2[C:20]([O:21][CH2:22][CH2:23][CH:24]([C:25]([F:28])([F:26])[F:27])[C:29]([F:30])([F:31])[F:32])=[CH:19][C:18]([CH3:33])=[CH:17][N:16]2[C:34]=1[C:35]([OH:37])=[O:36]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 17749109Barium hydroxide, octahydrateHCID 86717933Ethyl 2,6-dimethyl-8-[4,4,4-trifluoro-3-(trifluoromethyl)butoxy]imidazo[1,2-a]pyridine-3-carboxylate

Product 1

HCID 867179342,6-Dimethyl-8-[4,4,4-trifluoro-3-(trifluoromethyl)butoxy]imidazo[1,2-a]pyridine-3-carboxylic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

3.28 g (10.4 mmol) of barium hydroxide octahydrate were added to 1.95 g (4.73 mmol) of ethyl 2,6-dimethyl-8-[4,4,4-trifluoro-3-(trifluoromethyl)butoxy]imidazo[1,2-a]pyridine-3-carboxylate Example 258A in 30 ml of methanol, and the mixture was stirred at RT for 3 days. The suspension was diluted with 30 ml of water and adjusted to pH 6 with 1 M hydrochloric acid. The solid was filtered off, washed with 50 ml of water and dried under reduced pressure at 70° C. for 2 h. This gave 1.64 g of the target compound (90% pure, 81% of theory).

Workup

  1. filtrationThe solid was filtered off
  2. washwashed with 50 ml of water
  3. customdried under reduced pressure at 70° C. for 2 h

Sources & evidence

ORD record
ord-637c011c8bb24e8bb77a98d201ed09d3
Source dataset
uspto-grants-2015_09
Patent number
US09126998B2

Reaction notes

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