Lithium Hydroxide → 4-(3-Amino-6-(oxetan-3-yl)pyrazin-2-yl)-2-fluorobenzoic acid

HRID 596110Notes

Reaction equation

HRID 596110 reaction equation
[NH2:1][C:2]1[C:3]([C:12]2[CH:21]=[CH:20][C:15]([C:16]([O:18]C)=[O:17])=[C:14]([F:22])[CH:13]=2)=[N:4][C:5]([CH:8]2[CH2:11][O:10][CH2:9]2)=[CH:6][N:7]=1.[Li+].[OH-]>CO.C1COCC1>[NH2:1][C:2]1[C:3]([C:12]2[CH:21]=[CH:20][C:15]([C:16]([OH:18])=[O:17])=[C:14]([F:22])[CH:13]=2)=[N:4][C:5]([CH:8]2[CH2:11][O:10][CH2:9]2)=[CH:6][N:7]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 118045687Methyl 4-(3-amino-6-(oxetan-3-yl)pyrazin-2-yl)-2-fluorobenzoate

Product 1

HCID 1180454324-(3-Amino-6-(oxetan-3-yl)pyrazin-2-yl)-2-fluorobenzoic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To methyl 4-(3-amino-6-(oxetan-3-yl)pyrazin-2-yl)-2-fluorobenzoate (13 mg, 0.043 mmol) in MeOH (1 mL) and THF (2 mL) was added LiOH (0.128 mL, 0.128 mmol). The reaction mixture was stirred 2 h at room temperature. The reaction mixtures was adjusted to acidic (pH˜3) and solvent was evaporated on rotovap. The crude was azeotrope with toluene and proceed for next step. LCMS (m/z): 290.1 (MH+), 0.46 min.

Workup

  1. customThe reaction mixtures
  2. customwas evaporated on rotovap
  3. custom290.1 (MH+), 0.46 min.

Sources & evidence

ORD record
ord-4f5aa3aedde04e5a9b1a344750d81475
Source dataset
uspto-grants-2016_01
Patent number
US09242996B2

Reaction notes

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