4-(2-bromoacetyl)benzoic Acid → 4-[2-(Pyridin-3-ylamino)-thiazol-4-yl]-benzoic acid

HRID 606606Notes

Reaction equation

HRID 606606 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([NH:7][C:8]([NH2:10])=[S:9])[CH:2]=1.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]=[C:3]([NH:7][C:8]2[S:9][CH:12]=[C:13]([C:15]3[CH:23]=[CH:22][C:18]([C:19]([OH:21])=[O:20])=[CH:17][CH:16]=3)[N:10]=2)[CH:2]=1

Participants

4

Reactant 2

HCID 27568364-(2-bromoacetyl)benzoic AcidHCID 27605153-Pyridylthiourea

Product 1

HCID 181865234-[2-(Pyridin-3-ylamino)-thiazol-4-yl]-benzoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Pyridin-3-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-65a086b1b52a4f5b855352a5d7ef6cf0
Source dataset
uspto-grants-2011_03
Patent number
US07915300B2

Reaction notes

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