aluminum chloride yields the chloroketone ( 42 ). Reaction of that with
pyrrolidine ( 40 ) leads to the alkylation product 43. Catalytic hydrogenation
over palladium reduces the aryl carbonyl group to a methylene probably
via the initially formed labile benzyl alcohol. Thus the anticholinergic
agent 44 is obtained.^4
HO NH
CO 2 H
34
heat NH
HO
35
CH 3 C 6 H 4 SO 2 CH 3
HO NSO^3 C^6 H^4 CH^3 DEAD; Ph 3 PCH 3 C 6 H 5 SO 2 NSO 3 C 6 H 4 CH 3
36
CH 3 C 6 H 4 SO 2 Cl
CN
CN
NSO 3 C 6 H 4 CH 3
39
37
38
NaH
- HBr
- H 2 SO 4
CONH 2
NH
40
O
41
Cl COCl
O
42
O
Cl
CONH 2
43
O
O
N
H 2 CONH 2
44
O
N
Protein kinases comprise a series of closely related enzymes that cata-
lyze the phosphorylation of hydroxyl groups in enzymes, which regulate
a wide range of physiological processes. Phosphorylation may either turn
the function of the target on or off. Inhibitors of the protein C kinases
(PKC) that are involved in cell proliferation have attracted particular
HN
N N
O
O O
N(CH 3 ) 2
Ruboxystaurin
88 FIVE-MEMBERED HETEROCYCLES