1-(2-Pyridyl)-2-thiourea → 4-{2-[(Pyridin-2-yl)amino]-1,3-thiazol-4-yl}benzoic acid

HRID 606607Notes

Reaction equation

HRID 606607 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][C:8]([NH2:10])=[S:9].Br[CH2:12][C:13]([C:15]1[CH:23]=[CH:22][C:18]([C:19]([OH:21])=[O:20])=[CH:17][CH:16]=1)=O>C1COCC1>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][C:8]1[S:9][CH:12]=[C:13]([C:15]2[CH:23]=[CH:22][C:18]([C:19]([OH:21])=[O:20])=[CH:17][CH:16]=2)[N:10]=1

Participants

4

Reactant 2

HCID 14904911-(2-Pyridyl)-2-thioureaHCID 27568364-(2-bromoacetyl)benzoic Acid

Product 1

HCID 598073464-{2-[(Pyridin-2-yl)amino]-1,3-thiazol-4-yl}benzoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Pyridin-2-yl-thiourea (2.06 mmol) and 4-(2-Bromo-acetyl)-benzoic acid (2.06 mmol) were mixed in THF (12 mL). After stirring at room temperature for 5 minutes the mixture was heated to 80° C. for 2 hours. The mixture was then cooled to room temperature and filtered. The solid was washed with a small amount of diethylether and dried. m/z=298.0 in MS ES+, which was characterized by hplc and MS and used in the next step without any further purification.

Workup

  1. temperaturewas heated to 80° C. for 2 hours
  2. temperatureThe mixture was then cooled to room temperature
  3. filtrationfiltered
  4. washThe solid was washed with a small amount of diethylether
  5. customdried
  6. customused in the next step without any further purification

Sources & evidence

ORD record
ord-106fb34b6a13461da2f65e9b807da571
Source dataset
uspto-grants-2011_03
Patent number
US07915300B2

Reaction notes

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