N-((1R,2S,5R)-5-(TERT-BUTYLAMINO)-2-((S)-3-(7-TERT-BUTYLPYRAZOLO[1,5-A][1,3,5]TRIAZIN-4-YLAMINO)-2-OXOPYRROLIDIN-1-YL)CYCLOHEXYL)ACETAMIDE, A DUAL MODULATOR OF CHEMOKINE RECEPTOR ACTIVITY, CRYSTALLINE FORMS AND PROCESSES

摘要

Abstract A process for preparing a compound of formula I, or a salt form thereof: rN CH3 Ra R9 O =H G -a a I-cc I-bb RI R9 comprising: 1) converting a hydrazone compound of formula I-cc to a compound of formula I-bb; and 2) coupling the compound of formula I-bb with a compound of formula I aa; wherein: R 1 is independently hydrogen or an amine-protecting group selected from a carbobenzyloxy group, a tert-butyloxycarbony 1, a fluorenylmethyloxycarbonyl group, a benzyl group, and a p-methoxybenzyl group; R8 and R9 are independently hydrogen or C1.6 alkyl; R2 is =0; HET is an optionally substituted 3-to 14-membered heterocyclo or heteroaryl bicyclic ring having at least one nitrogen heteroatom; and LG is -OR 16 , wherein R16 is C1.6alkyl, phenyl, a 5-to 7-membered heteroaryl having one or more atoms selected from N, S, or 0, or a 3-to 7 membered cycloalkyl, all of which are optionally substituted with 1 to 3 groups selected from halogen, CF 3or CI.6 alkyl.