Preparation of 2-heteroarylamine analogs

August 16, 2024

• Title:       

  Preparation of 2-heteroarylamine analogs

• Image Source:

  Discovery and SAR of 2-amino-5-(thioaryl)thiazoles as potent and selective Itk inhibitors

• Mark:

  Scheme 3

• Associated context:

  Preparation of 2-heteroarylamine analogs required a different approach as illustrated in Scheme 3 with the synthesis of 2-aminopyridine (CAS 504-29-0) 18. The reaction of 2-amino-pyridine 14 with benzoylisothiocyanate (CAS 532-55-8) in acetone (CAS 67-64-1) followed by basic hydrolysis of the benzoyl protecting group afforded a thiourea intermediate9 which was condensed with chloroacetaldehyde10 in aq ethanol to form thiazole 15.