Practical syntheses of a CXCR3 antagonist

J Chan, BJ Burke, K Baucom, K Hansen…

Index: Chan, Johann; Burke, Brenda J.; Baucom, Kyle; Hansen, Karl; Bio, Matthew M.; DiVirgilio, Evan; Faul, Margaret; Murry, Jerry Journal of Organic Chemistry, 2011 , vol. 76, # 6 p. 1767 - 1774

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Citation Number: 8

Abstract

Two new, reliable syntheses of a pyrido [2, 3-d]-pyrimidine inhibitor of the CXCR3 receptor are described. A nine-step synthesis of the CXCR3 inhibitor (1) from 2-aminonicotinic acid was demonstrated on a multikilogram scale and incorporates a classic resolution to deliver the enantioenriched active pharmaceutical ingredient (API). A second synthesis of the CXCR3 inhibitor starts from (+)-(d)-Boc alanine and 2-chloronicotinic acid and utilizes a ...