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Generated: August 20, 2017

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Title:Macrocyclic quinoxaline compounds as HCV NS3 protease inhibitors
Abstract: The present invention relates to macrocyclic a compound of formula (I) and its use as inhibitors of the hepatitis C virus (HCV) NS3 protease, and in treating or preventing HCV infections. ##STR00001##
Inventor(s): Harper; Steven (Pomezia, IT), Summa; Vincenzo (Pomezia, IT), Liverton; Nigel J. (Harleysville, PA), McCauley; John A. (Maple Glen, PA)
Assignee: Insituto di Ricerche di Biologia Molecolare P. Angeletti SpA (Rome, IT) Merck Sharp & Dohme Corp. (Rahway, NJ)
Filing Date:May 20, 2011
Application Number:13/112,281
Claims:1. A method of preparing a compound of formula (I): ##STR00029## said method comprising: reacting (1aR,5S,8S,10R,22aR)-5-tert-butyl-14-methoxy-3,6-dioxo-1,1a,3,4,5,6,9,10,- 18,19,20,21,22,22a-tetradecahydro-8H-7,10-methanocyclopropa[18,19][1,10,3,- 6]dioxadiazacyclononadecino[11,12-b]quinoxaline-8-carboxylic acid ##STR00030## with (1R,2S)-1-Amino-N-(cyclopropylsulfonyl)-2-vinylcyclopropanecarboxamide hydrochloride ##STR00031##

2. The method of claim 1, wherein the reacting is conducted in the presence of at least one reagent selected from the group consisting of diisopropylethylamine (DIEA), dimethylamino pyridine (DMAP) and O-benzotriazol-1-yl-N,N,N',N'-tetramethyluronium tetrafluoroborate (TBTU).

3. The method of claim 1, wherein the reacting is conducted in the presence of diisopropylethylamine (DIEA), dimethylamino pyridine (DMAP) and O-benzotriazol-1-yl-N,N,N',N'-tetramethyluronium tetrafluoroborate (TBTU).

4. A method of preparing a pharmaceutically acceptable salt of a compound of formula (I): ##STR00032## said method comprising: reacting a compound of formula (I) with a metal alkoxide to form a salt or the compound of formula (I).

5. The method of claim 4, wherein the metal alkoxide is a potassium alkoxide.

6. The method of claim 5, wherein the potassium alkoxide is a potassium tert-butoxide.

7. A compound prepared by the method of claim 1.

8. A compound prepared by the method of claim 4.
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