Hydrochloric Acid → 4-(3-Amino-6-cyclopropylpyrazin-2-yl)-2-fluorobenzoic acid

HRID 596074Notes

Reaction equation

HRID 596074 reaction equation
[NH2:1][C:2]1[C:3]([C:11]2[CH:20]=[CH:19][C:14]([C:15]([O:17]C)=[O:16])=[C:13]([F:21])[CH:12]=2)=[N:4][C:5]([CH:8]2[CH2:10][CH2:9]2)=[CH:6][N:7]=1.[Li+].[OH-].Cl>C1COCC1.CO>[NH2:1][C:2]1[C:3]([C:11]2[CH:20]=[CH:19][C:14]([C:15]([OH:17])=[O:16])=[C:13]([F:21])[CH:12]=2)=[N:4][C:5]([CH:8]2[CH2:9][CH2:10]2)=[CH:6][N:7]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 118045452Methyl 4-(3-amino-6-cyclopropylpyrazin-2-yl)-2-fluorobenzoate

Product 1

HCID 1180458224-(3-Amino-6-cyclopropylpyrazin-2-yl)-2-fluorobenzoic acidYield 97%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To methyl 4-(3-amino-6-cyclopropylpyrazin-2-yl)-2-fluorobenzoate (250 mg, 0.870 mmol) in THF (6 mL) and MeOH (3 mL) was added 1M LiOH (1.740 mL, 1.740 mmol). The reaction mixture was stirred at room temperature for 2 h. The pH of reaction mixtures was adjusted to ˜4 by aqueous. 2N HCl. The reaction mixture was partitioned between EtOAc and water. The organic layer was separated, washed with brine, dried over sodium sulfate, filtered and evaporated to yield 4-(3-amino-6-cyclopropylpyrazin-2-yl)-2-fluorobenzoic acid (230 mg, 97%) as a light yellow solid. LCMS (m/z): 274.2 (MH+), 0.621 min.

Workup

  1. customThe pH of reaction mixtures
  2. customThe reaction mixture was partitioned between EtOAc and water
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-cf523c83896c48c9b5c6a2c76fd07caa
Source dataset
uspto-grants-2016_01
Patent number
US09242996B2

Reaction notes

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