title: Direct, metal-free amination of heterocyclic amides/ureas with NH-heterocycles and N-substituted anilines in POCl3.
abstract: A POCl(3)-mediated, direct amination reaction of heterocyclic amides/ureas with NH-heterocycles or N-substituted anilines is described. Compared to the existing methods, this operationally simple protocol provides unique reactivity and functional group compatibility because of the metal-free, acidic reaction conditions. The yields are generally excellent.
authors: Johnson & Johnson Pharmaceutical Research & Development, LLC, 3210 Merryfield Row, San Diego, California 92121, United States. xdeng@its.jnj.com
authors: Xiaohu
authors: X
authors: Deng
authors: Armin
authors: A
authors: Roessler
authors: Ivana
authors: I
authors: Brdar
authors: Roger
authors: R
authors: Faessler
authors: Jiejun
authors: J
authors: Wu
authors: Zachary S
authors: ZS
authors: Sales
authors: Neelakandha S
authors: NS
authors: Mani
mesh_terms: D000577:Amides / Q000737:chemistry*; D000586:Amination; D000814:Aniline Compounds / Q000737:chemistry; D000924:Anticholesteremic Agents / Q000032:analysis / Q000737:chemistry; D053961:Azabicyclo Compounds / Q000032:analysis / Q000737:chemistry; D001549:Benzamides; D002384:Catalysis; D002626:Chemistry, Pharmaceutical / Q000379:methods*; D000069347:Erlotinib Hydrochloride; D000069582:Eszopiclone; D005464:Fluorobenzenes / Q000032:analysis / Q000737:chemistry; D006571:Heterocyclic Compounds / Q000032:analysis / Q000138:chemical synthesis*; D006801:Humans; D006863:Hydrogen-Ion Concentration; D006993:Hypnotics and Sedatives / Q000032:analysis / Q000737:chemistry; D007004:Hypoglycemic Agents / Q000032:analysis / Q000737:chemistry; D000068877:Imatinib Mesylate; D015394:Molecular Structure; D017553:Phosphorus Compounds / Q000737:chemistry; D010879:Piperazines / Q000032:analysis / Q000737:chemistry; D055553:Prescription Drugs / Q000032:analysis / Q000138:chemical synthesis*; D047428:Protein Kinase Inhibitors / Q000032:analysis / Q000737:chemistry; D011743:Pyrimidines / Q000032:analysis / Q000737:chemistry; D011799:Quinazolines / Q000032:analysis / Q000737:chemistry; D000077154:Rosiglitazone; D000068718:Rosuvastatin Calcium; D013449:Sulfonamides / Q000032:analysis / Q000737:chemistry; D045162:Thiazolidinediones / Q000032:analysis / Q000737:chemistry; D014508:Urea / Q000031:analogs & derivatives / Q000737:chemistry*
chemical_list: D000577:Amides; D000814:Aniline Compounds; D000924:Anticholesteremic Agents; D053961:Azabicyclo Compounds; D001549:Benzamides; D005464:Fluorobenzenes; D006571:Heterocyclic Compounds; D006993:Hypnotics and Sedatives; D007004:Hypoglycemic Agents; D017553:Phosphorus Compounds; D010879:Piperazines; D055553:Prescription Drugs; D047428:Protein Kinase Inhibitors; D011743:Pyrimidines; D011799:Quinazolines; D013449:Sulfonamides; D045162:Thiazolidinediones; D000077154:Rosiglitazone; D000068718:Rosuvastatin Calcium; D000068877:Imatinib Mesylate; D014508:Urea; C013196:phosphoryl chloride; D000069347:Erlotinib Hydrochloride; C023650:aniline; D000069582:Eszopiclone