Sodium hydride → 3-[2-(Pyridin-2-ylamino)thiazol-5-ylmethylsulfanyl]benzoic acid

HRID 6869

Reaction equation

HRID 6869 reaction equation
[SH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].[H-].[Na+].Cl.Cl[CH2:15][C:16]1[S:20][C:19]([NH:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=2)=[N:18][CH:17]=1.S([O-])(O)(=O)=O.[K+]>>[N:23]1[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=1[NH:21][C:19]1[S:20][C:16]([CH2:15][S:1][C:2]2[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=2)[C:5]([OH:7])=[O:6])=[CH:17][N:18]=1

Participants

5

Reactant 4

HCID 24758Sodium hydrideHCID 95737Benzoic acid, 3-mercapto-HCID 516920Potassium bisulfateHCID 86591883(5-Chloromethylthiazol-2-yl)pyridin-2-ylamine hydrochloride

Product 1

HCID 220190553-[2-(Pyridin-2-ylamino)thiazol-5-ylmethylsulfanyl]benzoic acid

Procedure

A mixture of 3-mercaptobenzoic acid (308 mg, 2 mmol) and sodium hydride (60% in oil, 160 mg, 4 mmol) was stirred at RT under argon for 10 min and then cooled to 0° C. and (5-chloromethyl-thiazol-2-yl)pyridin-2-yl-amine hydrochloride salt (262 mg, 1 mmol) was added. The resulting reaction mixture was stirred at 0° C. for 1 h and acidified with 1N potassium hydrogen sulfate solution to pH=4. The mixture was filtered and the collected solid was washed with water and dried in vacuo to provide compound 11A, 3-[2-(pyridin-2-ylamino)thiazol-5-ylmethylsulfanyl]benzoic acid, which was used directly for the next step.

Workup

  1. temperaturecooled to 0° C.
  2. customThe resulting reaction mixture
  3. stirringwas stirred at 0° C. for 1 h
  4. filtrationThe mixture was filtered
  5. washthe collected solid was washed with water
  6. customdried in vacuo

Sources & evidence

ORD record
ord-291beb463c0d4332921ff3a2d84bcb76
Source dataset
uspto-grants-2006_08
Patent number
US07084160B2

Linked notes

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