Methodology for the preparation of 2-argininylbenzothiazole.
An efficient process to produce kilogram quantities of a key argininylbenzo[d]thiazole intermediate was developed for the preparation of the tryptase inhibitor RWJ-56423. A variety of activated arginine esters and benzo[d]thiazole nucleophiles were evaluated as coupling partners. Our work led to the selection and optimization of an argininyl imidazolide ester and benzothiazol-2-yl MgCl nucleophile. This paper focuses on the preparation, use, and stability of the benzothiazol-2-yl Grignard reagents.
Kenney
Birdella D
BD
Johnson & Johnson Pharmaceutical Research and Development, Raritan, New Jersey 08869, USA. birdellakenney@yahoo.com
Breslav
Michael
M
Chang
Rosie
R
Glaser
Roland
R
Harris
Bruce D
BD
Maryanoff
Cynthia A
CA
Mills
John
J
Roessler
Armin
A
Segmuller
Brigitte
B
Villani
Frank J
FJ
D001120:Arginine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D052160:Benzothiazoles / Q000138:chemical synthesis / Q000737:chemistry*; D003460:Crystallization; D007093:Imidazoles / Q000737:chemistry*; D015394:Molecular Structure; D013997:Time Factors
C526563:2-argininylbenzothiazole; D052160:Benzothiazoles; D007093:Imidazoles; D001120:Arginine