Sodium Hydroxide → HCID 24825977, compound

HRID 910925Notes

Reaction equation

HRID 910925 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([NH:7][C:8]2[CH:13]=[C:12]([O:14][C:15]3[CH:16]=[C:17]([CH:22]=[CH:23][CH:24]=3)[C:18]([O:20]C)=[O:19])[CH:11]=[CH:10][N:9]=2)[S:5][CH:6]=1.[OH-].[Na+]>CO>[CH3:1][C:2]1[N:3]=[C:4]([NH:7][C:8]2[CH:13]=[C:12]([O:14][C:15]3[CH:16]=[C:17]([CH:22]=[CH:23][CH:24]=3)[C:18]([OH:20])=[O:19])[CH:11]=[CH:10][N:9]=2)[S:5][CH:6]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 24827108HCID 24827108, compound

Product 1

HCID 24825977HCID 24825977, compoundYield 78.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

A 250 mL round bottom flask was charged with methyl 3-(2-(4-methylthiazol-2-ylamino)pyridin-4-yloxy)benzoate (2.0 g, 5.859 mmol) and methanol (100 mL) was added. To this solution was added 1M NaOH (30 mL). The reaction mixture was heated at 60° C. with stirring for 3 hours. The reaction mixture was cooled and concentrated. To the residue was added 1% HCl and 0.5 mL 6N HCl. The solution was filtered and the residue was collected to give 3-(2-(4-methylthiazol-2-ylamino)pyridin-4-yloxy)benzoic acid (1.499 g, 77.38% yield) as a tan solid. 1H NMR (CDCl3) δ 8.24 (d, 1H), 7.94 (dt, 1H), 7.79 (t, 1H), 7.52 (t, 1H), 7.33 (ddd, 1H), 6.86 (bs, 1H), 6.68 (dd, 1H), 6.39 (d, 1H), 2.45 (d, 3H); Mass spectrum (apci) m/z=328 (100) (M+H).

Workup

  1. additionwas added
  2. temperatureThe reaction mixture was cooled
  3. concentrationconcentrated
  4. additionTo the residue was added 1% HCl and 0.5 mL 6N HCl
  5. filtrationThe solution was filtered
  6. customthe residue was collected

Sources & evidence

ORD record
ord-3866568fd1214cce87bdc3780f8b94d0
Source dataset
uspto-grants-2011_09
Patent number
US08022222B2

Reaction notes

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