Hydrochloric Acid → 2-(Ethylsulfanyl)-6-morpholin-4-yl-4-(trifluoromethyl)-pyridine-3-carboxylic acid

HRID 1753864Notes

Reaction equation

HRID 1753864 reaction equation
[CH2:1]([S:3][C:4]1[C:9]([C:10]([O:12]C)=[O:11])=[C:8]([C:14]([F:17])([F:16])[F:15])[CH:7]=[C:6]([N:18]2[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)[N:5]=1)[CH3:2].CO.C1COCC1.[Li+].[OH-].Cl>CCOC(C)=O>[CH2:1]([S:3][C:4]1[C:9]([C:10]([OH:12])=[O:11])=[C:8]([C:14]([F:17])([F:16])[F:15])[CH:7]=[C:6]([N:18]2[CH2:19][CH2:20][O:21][CH2:22][CH2:23]2)[N:5]=1)[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 21899815MeOH tetrahydrofuranHCID 67287001HCID 67287001, compound

Product 1

HCID 672876242-(Ethylsulfanyl)-6-morpholin-4-yl-4-(trifluoromethyl)-pyridine-3-carboxylic acidYield 42%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 440 mg (1.3 mmol) methyl 2-(ethylsulfanyl)-6-morpholin-4-yl-4-(trifluoromethyl)-pyridine-3-carboxylate in a MeOH/THF mixture (6 ml, 1:1 v/v) was treated with a 2M aq. LiOH sol. (3 ml) and was then stirred at 60° C. for 5 d. After cooling to RT the RM was acidified with a 2M aq. HCl sol. to pH 2. Upon dilution with EtOAc the precipitate formed was filtered off to give 176 mg (0.5 mmol, 42%) 2-(ethylsulfanyl)-6-morpholin-4-yl-4-(trifluoromethyl)-pyridine-3-carboxylic acid, which was used in the next step without further purification.

Workup

  1. temperatureAfter cooling to RT the RM
  2. filtrationwas filtered off

Sources & evidence

ORD record
ord-b4f0aec315b343e69a71760e645442d2
Source dataset
uspto-grants-2015_10
Patent number
US09168259B2

Reaction notes

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