Tetrahydrofuran → HCID 66749149, compound

HRID 537039Notes

Reaction equation

HRID 537039 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[C:9]([C:11]2[O:12][C:13]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[Cl:26])=[C:14]([C:16]([O:18]C)=[O:17])[N:15]=2)[C:8]([CH3:27])=[CH:7][N:6]=1)(=[O:3])[CH3:2].C1COCC1.[OH-].[Na+]>CO>[C:1]([NH:4][C:5]1[CH:10]=[C:9]([C:11]2[O:12][C:13]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[Cl:26])=[C:14]([C:16]([OH:18])=[O:17])[N:15]=2)[C:8]([CH3:27])=[CH:7][N:6]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 66749418HCID 66749418, compound

Product 1

HCID 66749149HCID 66749149, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a round bottom flask was added methyl 2-[2-(acetylamino)-5-methylpyridin-4-yl]-5-(2-chlorophenyl)-1,3-oxazole-4-carboxylate (2.30 g, 6.0 mmol), THF (20 mL), MeOH (30 mL), and 1M aqueous NaOH (25 mL). The reaction mixture was allowed to stir at rt overnight. The mixture was concentrated and 1M aqueous HCl was added until the solution became acidic. The mixture was filtered and the solid was dried to give 2-[2-(acetylamino)-5-methylpyridin-4-yl]-5-(2-chlorophenyl)-1,3-oxazole-4-carboxylic acid (Compound I-6) (1.4 g, 64%). LCMS (FA): m/z=372.2 (M+H).

Workup

  1. concentrationThe mixture was concentrated
  2. addition1M aqueous HCl was added until the solution
  3. filtrationThe mixture was filtered
  4. customthe solid was dried

Sources & evidence

ORD record
ord-0492850dcbda4079b0056f63c781acd9
Source dataset
uspto-grants-2014_10
Patent number
US08859768B2

Reaction notes

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