title: Synthesis toward CRHR1 Antagonists through 2,7-Dimethylpyrazolo[1,5-α][1,3,5]triazin-4(3H)-one C-H Arylation.
abstract: A novel synthetic protocol for 8-aryl substituted pyrazolo[1,5-α][1,3,5]triazin-4(3H)-ones was developed employing Pd-catalyzed C-H arylation. The reaction yield was influenced by the presence of a phosphine ligand, pivalic acid, and base selection. With the use of 5-10 mol % catalyst, reactions of 2 with p- or m-substituted aryl bromides proceeded in moderate to good yields. Lower yields were observed with o-substituted aryl bromides. Using this method a precursor for MJL1-109-2, a known nonpeptide CRHR-1 antagonist, was successfully synthesized.
authors: Department of Chemistry, College of Natural Sciences, Seoul National University, Seoul 151-747, Republic of Korea.
authors: Jinghai
authors: J
authors: Long
authors: Department of Chemistry, College of Natural Sciences, Seoul National University, Seoul 151-747, Republic of Korea.
authors: Woong-Sup
authors: WS
authors: Lee
authors: Department of Chemistry, College of Natural Sciences, Seoul National University, Seoul 151-747, Republic of Korea.
authors: Chieyeon
authors: C
authors: Chough
authors: Department of Chemistry, College of Natural Sciences, Seoul National University, Seoul 151-747, Republic of Korea.
authors: Il Hak
authors: IH
authors: Bae
authors: Department of Chemistry, College of Natural Sciences, Seoul National University, Seoul 151-747, Republic of Korea.
authors: B Moon
authors: BM
authors: Kim
mesh_terms: D006801:Humans; D015394:Molecular Structure; D011720:Pyrazoles / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D018019:Receptors, Corticotropin-Releasing Hormone / Q000037:antagonists & inhibitors*; D014227:Triazines / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D000099052:CRF Receptor, Type 1
chemical_list: C000603392:2,7-dimethylpyrazolo(1,5-alpha)(1,3,5)triazin-4(3H)-one; D011720:Pyrazoles; D018019:Receptors, Corticotropin-Releasing Hormone; D014227:Triazines; D000099052:CRF Receptor, Type 1