Benzimidazole compounds
Provided are compounds having Formula VIIIa-1: wherein Z, X 5 , R 2 , R 2a and R 10 are as defined herein. Compounds of Formula VIIIa-1 can be used to prepare heterocyclic derivatives such as benzimidazole derivatives.
1. A compound having the Formula VIIIa-1
and salts and solvates thereof, wherein
Z is —C(═O)OR 1 , —C(═O)NR 6 R 7 , —C(═O)H, or
R 1 is hydrogen, C 1 -C 10 alkyl, C 2 -C 10 alkenyl, C 2 -C 10 alkynyl, C 3 -C 10 cycloalkyl, C 3 -C 10 cycloalkylalkyl, aryl, arylalkyl, heteroaryl, heteroarylalkyl, heterocyclyl, heterocyclylalkyl, trialkylsilyl, or dialkylarylsilyl, wherein said alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, heteroaryl, heteroarylalkyl, heterocyclyl and heterocyclylalkyl portions are optionally substituted with one or more groups independently selected from halogen, hydroxyl, C 1 -C 4 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C 3 -C 6 cycloalkyl and C 3 -C 6 heterocycloalkyl;
R 2 and R 2a are independently hydrogen, C 1 -C 10 alkyl, C 2 -C 10 alkenyl, C 2 -C 10 alkynyl, benzyl, allyl, arylalkyl, trialkylsilyl, dialkylarylsilyl, —COR 6 , —C(O)OR 6 or —C(O)NR 6 R 7 , wherein said alkyl, alkenyl, alkynyl, benzyl, allyl and arylalkyl portions are optionally substituted with one or more groups independently selected from halogen, hydroxyl, C 1 -C 4 alkyl, C 2 -C 4 alkenyl, and C 2 -C 4 alkynyl;
X 5 is, F, Cl, Br, I or C 1 -C 6 alkyl;
R 6 and R 7 are independently hydrogen, trifluoromethyl, —OR 8 , C 1 -C 10 alkyl, C 2 -C 10 alkenyl, C 2 -C 10 alkynyl, C 3 -C 10 cycloalkyl, C 3 -C 10 cycloalkylalkyl, aryl, arylalkyl, heteroaryl, heteroarylalkyl, heterocyclyl or heterocyclylalkyl,
or R 6 and R 7 together with the atom to which they are attached form a 4 to 10 membered heteroaryl or heterocyclic ring, wherein said heteroaryl and heterocyclic rings are optionally substituted with one or more groups independently selected from halogen, trifluoromethyl, difluoromethoxy, trifluoromethoxy and OR 8 ;
R 8 is hydrogen, C 1 -C 10 alkyl, C 2 -C 10 alkenyl, aryl or arylalkyl, wherein said alkyl, alkenyl, aryl and arylalkyl are optionally substituted with one or more groups independently selected from OH, O—(C 1 -C 10 -alkyl) and —O—(C 1 -C 10 -alkenyl); and
R 10 is C 1 -C 10 alkyl, C 3 -C 10 cycloalkylalkyl, arylalkyl, heteroarylalkyl or heterocyclylalkyl, wherein said alkyl, cycloalkylalkyl, arylalkyl, heteroarylalkyl and heterocyclylalkyl portions are optionally substituted with one or more groups independently selected from halogen, hydroxyl, cyano, nitro, azido, C 1 -C 4 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C 3 -C 6 cycloalkyl, C 3 -C 6 heterocycloalkyl, —NR 6 R 7 and —OR 8 .
2. The compound of claim 1 , wherein Z is —C(═O)NR 6 R 7 , wherein R 6 is —OR 8 , R 7 is H and R 8 is —(CH 2 ) 2 —OH.
3. The compound of claim 1 , wherein Z is —COOR 1 and R 1 is C 1-10 alkyl.
4. The compound of claim 3 , wherein R 1 is methyl.