Sodium Hydroxide → HCID 2866632, compound

HRID 1357668Notes

Reaction equation

HRID 1357668 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[N:8]=[C:9]([NH:12][C:13]3[CH:14]=[C:15]([CH:20]=[CH:21][CH:22]=3)[C:16]([O:18]C)=[O:17])[S:10][CH:11]=2)=[CH:3][CH:2]=1.[OH-].[Na+]>CO.C1COCC1>[N:1]1[CH:2]=[CH:3][C:4]([C:7]2[N:8]=[C:9]([NH:12][C:13]3[CH:14]=[C:15]([CH:20]=[CH:21][CH:22]=3)[C:16]([OH:18])=[O:17])[S:10][CH:11]=2)=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 18186658Methyl 3-[[4-(4-pyridinyl)-2-thiazolyl]amino]benzoate

Product 1

HCID 2866632HCID 2866632, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

A solution of methyl 3-(4-pyrid-4-ylthiazol-2-ylamino)benzoate (500 mg, 1.27 mmol) in a 3/2 mixture of methanol/THF (100 mL) was treated with an aqueous solution of sodium hydroxide ((240 mg, 6 mmol, 20 mL). The reaction mixture was stirred at 40° C. for approximately 12 hours and then concentrated. The residue was diluted with water (20 mL) and the diluted solution was acidified to pH 5 with dilute hydrochloric acid. A resulting solid was collected by filtration and washed with water to provide 3-(4-pyrid-4-ylthiazol-2-ylamino)benzoic acid (328 mg, 87% yield). HNMR (dmso-d6): 10.80 (1H, s), 8.63 (2H, m), 7.90 (7H, m). LC/MS: M+1: 297.86.

Workup

  1. concentrationconcentrated
  2. additionThe residue was diluted with water (20 mL)
  3. filtrationA resulting solid was collected by filtration
  4. washwashed with water

Sources & evidence

ORD record
ord-7873f45f8d124b689f83605fd56e2c9e
Source dataset
uspto-grants-2003_07
Patent number
US06593327B2

Reaction notes

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