Lithium Hydroxide → HCID 59370290, compound

HRID 705100Notes

Reaction equation

HRID 705100 reaction equation
C([O:3][C:4](=[O:26])[C:5]1[CH:10]=[C:9]([C:11]2[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][N:12]=2)[CH:8]=[C:7]([C:18]2[S:22][N:21]=[N:20][C:19]=2[CH:23]([CH3:25])[CH3:24])[CH:6]=1)C.[Li+].[OH-]>C1COCC1>[CH:23]([C:19]1[N:20]=[N:21][S:22][C:18]=1[C:7]1[CH:6]=[C:5]([CH:10]=[C:9]([C:11]2[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][N:12]=2)[CH:8]=1)[C:4]([OH:26])=[O:3])([CH3:25])[CH3:24]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 59370283HCID 59370283, compound

Product 1

HCID 59370290HCID 59370290, compoundYield 86.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 3-(4-isopropyl-[1,2,3]thiadiazol-5-yl)-5-(5-methyl-pyridin-2-yl)-benzoic acid ethyl ester (250 mg, 0.68 mmol) in 10 mL THF was cooled to 0° C., and LiOH (0.5 mL of 2N aqueous solution) was added. The reaction mixture was allowed to warm to room temperature and was stirred for 16 hours. The reaction mixture was concentrated under reduced pressure and the residue was acidified with 3N aqueous HCl to a pH of 6. The mixture was extracted with ethyl actetate, and the combined organic fractions were washed with brine, dried over MgSO4, filtered and concentrated under reduced pressure to give 200 mg of 3-(4-isopropyl-[1,2,3]thiadiazol-5-yl)-5-(5-methyl-pyridin-2-yl)-benzoic acid, MS (M+H)=340.

Workup

  1. temperatureto warm to room temperature
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. extractionThe mixture was extracted with ethyl actetate
  4. washthe combined organic fractions were washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-416afa539ff14f7692ce061903d02695
Source dataset
uspto-grants-2015_11
Patent number
US09173861B2

Reaction notes

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