Scalable Asymmetric Synthesis of the All Cis Triamino Cyclohexane Core of BMS-813160

Author:

La Cruz Thomas E.1ORCID,González-Bobes Francisco1ORCID,Eastgate Martin D.1ORCID,Sfouggatakis Chris1,Zheng Bin1ORCID,Kopp Nathaniel1,Xiao Yi,Fan Yu,Galindo Kay A.,Pathirana Charles1,Galella Michael A.2,Deerberg Joerg

Affiliation:

1. Chemical Process Development, Bristol Myers Squibb, One Squibb Drive, New Brunswick, New Jersey 08903-0191, United States

2. Analytical Strategy & Operations, Bristol Myers Squibb, One Squibb Drive, New Brunswick, New Jersey 08903-0191, United States

Publisher

American Chemical Society (ACS)

Subject

Organic Chemistry

Reference59 articles.

1. aCarter, P. H.; Cherney, R. J.; Batt, D. G.; Duncia, J. V.; Gardner, D. S.; Ko, S. S.; Srivastava, A. S.; Yang, M. G. Preparation of N-heterocycle derivatives as modulators of chemokine receptor activity. WO 2005021500, March 10, 2005.

2. bCarter, P. H.; Cherney, R. J.; Hynes, J.; Ko, S. S.; Srivastava, A.; Xiao, Z.; Yang, M. G. Preparation of Pyrrolidin-2-one Derivatives as Chemokine Receptor Modulators. WO 2008014361, January 31, 2008.

3. cCarter, P. H.; Cherney, R. J.; Rosso, V. W.; Li, J. Preparation of Pyrazolo[1,5-a][1,3,5]triazine Compound as CCR-2 and CCR-5 Dual Modulator. US 20110086857, April 14, 2011.

4. dAytar, Burcu Selin; Borovika, A.; Chan, C.; Deerberg, J.; Domagalski, N. R.; Eastgate, M. D.; Fan, Y.; Fenster, M. D. B.; Forest, R. V.; Gonzalez-Bobes, F.; Green, R. A.; Hickey, M. R.; Kopp, N. D.; La Cruz, T. E.; Lauser, K.; Lee, H. G.; Leahy, D. K.; Luo, H. Y.; Razler, T. M.; Savage, S. A.; Sfouggatakis, C.; Soumeillant, M. C. D.; Zaretsky, S.; Zheng, B.; Zhu, Y. Process for the Preparation of 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. WO 2019018592, January 24, 2019.

5. aYoshino, T.; Nagata, T.; Haginoya, N.; Yoshikawa, K.; Kanno, H.; Nagamochi, M. Preparation of Ethylenediamine and 1,2-Ccycloalkanediamine Derivatives as Inhibitors of Activated Blood Coagulation Factor X. WO 2001074774, October 11, 2001.

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