ChemicalBook CAS DataBase List Maraviroc

Maraviroc synthesis

12synthesis methods

Product Name:Maraviroc
CAS Number:376348-65-1
Molecular formula:C29H41F2N5O
Molecular Weight:513.68

Maraviroc is an antiviral, potent, non-competitive CKR-5 receptor antagonist that inhibits binding of HIV viral coat protein gp120. Maraviroc inhibits MIP-1β-stimulated γ-S-GTP binding to HEK-293 cell membranes, indicating its ability to inhibit chemokine-dependent stimulation of GDP-GTP exchange at the CKR-5/G protein complex. Maraviroc also inhibits the downstream event of chemokine-induced intracellular calcium redistribution.

Synthetic Routes

ROUTE 1

ROUTE 2

ROUTE 3

ROUTE 4

ROUTE 5

ROUTE 6

ROUTE 7

ROUTE 8

ROUTE 9

ROUTE 10

Lou, Sha; Moquist, Philip N.; Schaus, Scott E. Asymmetric Allylboration of Acyl Imines Catalyzed by Chiral Diols. Journal of the American Chemical Society. Volume 129. Issue 49. Pages 15398-15404. 2007.

423165-07-5 Synthesis

(1R,3s,5S)-3-(3-Isopropyl-5-methyl-4H-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octane

423165-07-5
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$60.00/100mg

376348-78-6 Synthesis

4,4-DIFLUORO-N-((1S)-3-OXO-1-PHENYLPROPYL)CYCLOHEXANE-1-CARBOXAMIDE

376348-78-6
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376348-65-1
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$35.00/5mg

Yield:376348-65-1 4.6 g

Reaction Conditions:

Stage #1:UK-408027;4,4-difluorocyclohexanecarboxylic acid (3-oxo-1-phenyl-propyl)-amide in tetrahydrofuran for 0.166667 h;Cooling with ice;
Stage #2: with acetic acid in tetrahydrofuran for 0.166667 h;
Stage #3: with sodium tris(acetoxy)borohydride in tetrahydrofuran

Steps:

6 Example 6: Preparation of Maraviroc
Compound (I) (3.09 g) as prepared in Example 5, compound (II) (2.34 g) as prepared in Example 4, and THF (30 g) were mixed in a round bottom flask. After the mixture was cooled in an ice bath and reacted for 10 min, HOAc (1.5 g) was added into the mixture and reacted for another 10 min. Subsequently, NaBH(OAc)₂(3.2 g) was added into the reaction mixture to reduce intermediate to crude product. The whole reaction mixture was quenched with 15% NaOH to pH >10. The organic phase was collected by phase separation, and concentrated under reduced pressure. Maraviroc (4.6 g) in a form of white powder was obtained from the concentrate by crystallization with EA.

References:

SCI Pharmtech, Inc.;Wang, Heng-Yen;Kao, Chen-Yi US2019/248782, 2019, A1 Location in patent:Paragraph 0030

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376348-71-9 Synthesis