Sodium Hydroxide → 4-Methyl-2-[(pyridine-4-carbonyl)amino]thiazole-5-carboxylic acid

HRID 45316

Reaction equation

HRID 45316 reaction equation
[C:1]([NH:9][C:10]1[S:11][C:12]([C:16]([O:18]CC)=[O:17])=[C:13]([CH3:15])[N:14]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.[OH-].[Na+]>CO.O>[C:1]([NH:9][C:10]1[S:11][C:12]([C:16]([OH:18])=[O:17])=[C:13]([CH3:15])[N:14]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 719362Ethyl 2-(isonicotinamido)-4-methylthiazole-5-carboxylate

Product 1

HCID 822263324-Methyl-2-[(pyridine-4-carbonyl)amino]thiazole-5-carboxylic acidYield 89%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A mixture of ethyl 2-(isonicotinamido)-4-methylthiazole-5-carboxylate (1.46 g, 5.0 mmol) and sodium hydroxide (0.40 g, 10.00 mmol) in methanol (100 mL) and water (25 mL) was stirred at ambient temperature overnight and then heated to reflux for 2 h. The mixture was concentrated and then neutralized with 5% hydrochloric acid solution to pH 5˜6. The precipitate obtained was collected by filtration and dried to give the title compound in 89% yield (1.17 g); 1H NMR (DMSO-d5, 300 MHz) δ 8.74 (d, J=6.0 Hz, 2H), 7.93 (d, J=6.0 Hz, 2H), 2.46 (s, 3H); MS (ES+) m/z 264.1 (M+1).

Workup

  1. temperatureheated
  2. temperatureto reflux for 2 h
  3. concentrationThe mixture was concentrated
  4. customThe precipitate obtained
  5. filtrationwas collected by filtration
  6. customdried

Sources & evidence

ORD record
ord-b00f813201694d0c85e3131770ab7d6b
Source dataset
uspto-grants-2013_09
Patent number
US08541457B2

Linked notes

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