Hydrochloric Acid → 4-(3-amino-6-(1-ethyl-1H-pyrazol-4-yl)pyrazin-2-yl)-2-fluorobenzoic acid

HRID 596099Notes

Reaction equation

HRID 596099 reaction equation
[NH2:1][C:2]1[C:3]([C:15]2[CH:24]=[CH:23][C:18]([C:19]([O:21]C)=[O:20])=[C:17]([F:25])[CH:16]=2)=[N:4][C:5]([C:8]2[CH:9]=[N:10][N:11]([CH2:13][CH3:14])[CH:12]=2)=[CH:6][N:7]=1.[Li+].[OH-].Cl>CO.C1COCC1>[NH2:1][C:2]1[C:3]([C:15]2[CH:24]=[CH:23][C:18]([C:19]([OH:21])=[O:20])=[C:17]([F:25])[CH:16]=2)=[N:4][C:5]([C:8]2[CH:9]=[N:10][N:11]([CH2:13][CH3:14])[CH:12]=2)=[CH:6][N:7]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 118045915methyl 4-(3-amino-6-(1-ethyl-1H-pyrazol-4-yl)pyrazin-2-yl)-2-fluorobenzoate

Product 1

HCID 1180452614-(3-amino-6-(1-ethyl-1H-pyrazol-4-yl)pyrazin-2-yl)-2-fluorobenzoic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To methyl 4-(3-amino-6-(1-ethyl-1H-pyrazol-4-yl)pyrazin-2-yl)-2-fluorobenzoate (25 mg, 0.073 mmol) in MeOH (1 mL) and THF (2 mL) was added 1 M LiOH (0.220 mL, 0.2 20 mmol). The reaction mixture was stirred at room temperature for 4 h. The pH of reaction mixture was adjusted to ˜4 by 2 N HCl. The product was extracted with ethyl acetate twice. The combined organics extracts were washed with brine, dried over sodium sulfate, filtered, and evaporated. The residue was proceeded to next step without further purification. LCMS (m/z): 328.1 (MH+), 0.607 min.

Workup

  1. customThe pH of reaction mixture
  2. extractionThe product was extracted with ethyl acetate twice
  3. washThe combined organics extracts were washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was proceeded to next step without further purification
  8. custom328.1 (MH+), 0.607 min.

Sources & evidence

ORD record
ord-9e9c72e73e34427d95eed81f1fe29a3c
Source dataset
uspto-grants-2016_01
Patent number
US09242996B2

Reaction notes

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