Methanol → HCID 90409966, compound

HRID 516591Notes

Reaction equation

HRID 516591 reaction equation
[NH2:1][C:2]1[C:7]([F:8])=[C:6]([C:9]2[CH:14]=[CH:13][C:12]([C:15]#[N:16])=[CH:11][C:10]=2[F:17])[N:5]=[C:4]([C:18]([O:20]C)=[O:19])[C:3]=1[Cl:22].O.[OH-].[Li+].CO.O>O1CCCC1>[NH2:1][C:2]1[C:7]([F:8])=[C:6]([C:9]2[CH:14]=[CH:13][C:12]([C:15]#[N:16])=[CH:11][C:10]=2[F:17])[N:5]=[C:4]([C:18]([OH:20])=[O:19])[C:3]=1[Cl:22]

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 90408574HCID 90408574, compound

Product 1

HCID 90409966HCID 90409966, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a 50-mL round bottom flask, equipped with a stir bar, methyl 4-amino-3-chloro-6-(4-cyano-2-fluorophenyl)-5-fluoropicolinate (351 mg, 1.084 mmol) and lithium hydroxide hydrate (100 mg, 2.383 mmol) were dissolved in tetrahydrofuran (2.0 mL), methanol (2.0 mL) and H2O (1.0 mL). The reaction was stirred at room temperature for 2 hours. The solvent was then removed by rotary evaporator. The resulting solid was treated with H2O, which was then adjusted to pH-3.0 with 1 N HCl, and extracted with ethyl acetate (3× 50 mL). The combined organic layers were dried over anhydrous magnesium sulfate, filtered and concentrated. The resulting residue was purified by reverse phase chromatography (150 g C18, 0-100% acetonitrile in H2O), as needed, to afford the title compound as a white solid (0.058 g, 20%).

Workup

  1. customIn a 50-mL round bottom flask, equipped with a stir bar
  2. customThe solvent was then removed by rotary evaporator
  3. additionThe resulting solid was treated with H2O, which
  4. extractionextracted with ethyl acetate (3× 50 mL)
  5. dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe resulting residue was purified by reverse phase chromatography (150 g C18, 0-100% acetonitrile in H2O)

Sources & evidence

ORD record
ord-d3e7ad8db5aa4170bbca5c1a3a673d83
Source dataset
uspto-grants-2015_08
Patent number
US09113629B2

Reaction notes

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