Hydrochloric Acid → HCID 118045960, compound

HRID 596067Notes

Reaction equation

HRID 596067 reaction equation
[NH2:1][C:2]1[C:7]([C:8]2[CH:17]=[CH:16][C:11]([C:12]([O:14]C)=[O:13])=[C:10]([F:18])[CH:9]=2)=[CH:6][C:5]([C:19]2[C:20]([CH3:27])=[N:21][N:22]([CH:24]([F:26])[F:25])[CH:23]=2)=[CH:4][N:3]=1.[Li+].[OH-].Cl>C1COCC1.CO>[NH2:1][C:2]1[C:7]([C:8]2[CH:17]=[CH:16][C:11]([C:12]([OH:14])=[O:13])=[C:10]([F:18])[CH:9]=2)=[CH:6][C:5]([C:19]2[C:20]([CH3:27])=[N:21][N:22]([CH:24]([F:26])[F:25])[CH:23]=2)=[CH:4][N:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 118045319HCID 118045319, compound

Product 1

HCID 118045960HCID 118045960, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 4-(2-amino-5-(1-(difluoromethyl)-3-methyl-1H-pyrazol-4-yl)pyridin-3-yl)-2-fluorobenzoate (352 mg, 0.935 mmol) in THF (6236 μL) and MeOH (3118 μL) was added LiOH (1 M solution) (1684 μL, 1.684 mmol). The reaction mixture was stirred at room temperature. To the reaction mixture, 1 N HCl was added up to pH 5. The reaction mixture was extracted with EtOAc. The organic layer was dried over anhydrous sodium sulfate, filtered off, and concentrated in vacuo to provide crude 4-(2-amino-5-(1-(difluoromethyl)-3-methyl-1H-pyrazol-4-yl)pyridin-3-yl)-2-fluorobenzoic acid (88%). LCMS (m/z): 363.3 (MH+), 0.51 min.

Workup

  1. extractionThe reaction mixture was extracted with EtOAc
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered off
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f5cbe33c439647b0b18293ae81734275
Source dataset
uspto-grants-2016_01
Patent number
US09242996B2

Reaction notes

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