Hydrochloric Acid → 4-(3-Amino-6-(1-(methoxycarbonyl)piperidin-3-yl)pyrazin-2-yl)-2-fluorobenzoic acid

HRID 596094Notes

Reaction equation

HRID 596094 reaction equation
[NH2:1][C:2]1[N:3]=[CH:4][C:5]([CH:19]2[CH2:24][CH2:23][CH2:22][N:21]([C:25]([O:27][CH3:28])=[O:26])[CH2:20]2)=[N:6][C:7]=1[C:8]1[CH:13]=[CH:12][C:11]([C:14]([O:16]C)=[O:15])=[C:10]([F:18])[CH:9]=1.[Li+].[OH-].Cl>C1COCC1.CO>[NH2:1][C:2]1[C:7]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([OH:16])=[O:15])=[C:10]([F:18])[CH:9]=2)=[N:6][C:5]([CH:19]2[CH2:24][CH2:23][CH2:22][N:21]([C:25]([O:27][CH3:28])=[O:26])[CH2:20]2)=[CH:4][N:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 118046722Methyl 3-(5-amino-6-(3-fluoro-4-(methoxycarbonyl)phenyl)pyrazin-2-yl)piperidine-1-carboxylate

Product 1

HCID 1180453834-(3-Amino-6-(1-(methoxycarbonyl)piperidin-3-yl)pyrazin-2-yl)-2-fluorobenzoic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To methyl 3-(5-amino-6-(3-fluoro-4-(methoxycarbonyl)phenyl)pyrazin-2-yl)piperidine-1-carboxylate (50 mg, 0.129 mmol) in THF (4 mL) and MeOH (2 mL) was added 1 M LiOH (0.500 mL, 0.500 mmol). The reaction mixture was stirred at room temperature for 4 h. The reaction mixture pH was adjusted to ˜3 with 2 N HCl, and product was extracted with ethyl acetate. The EtOAc layer was separated, washed with brine, dried over sodium sulfate, filtered and evaporated. The residue was proceeded to next step without purification (40 mg, 83%). LCMS (m/z): 375.2 (MH+), 0.637 min.

Workup

  1. extractionwas extracted with ethyl acetate
  2. customThe EtOAc layer was separated
  3. washwashed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was proceeded to next step without purification (40 mg, 83%)
  8. custom375.2 (MH+), 0.637 min.

Sources & evidence

ORD record
ord-27b7d66ef04f4183b2f84cdfe353f00e
Source dataset
uspto-grants-2016_01
Patent number
US09242996B2

Reaction notes

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