Organic Chemistry of Drug Synthesis. Volume 7

the azepinone carbonyl group with borohydride affords the vasopressin
antagonisttolvaptan( 207 ).^29

NO 2

Cl CO 2 H

2. SnCl 2

1 .(CH 3 )SO 4

NH 2

Cl CO 2 CH 3

TsCl

NH

Cl CO 2 CH 3

195 196 197 Ts

CO 3 CH 2 H 5

Cl CO 3 CH 2 H 5

N

Cl CO 2 CH 3

199 Ts

198

N

Ts

O CO 2 R

Cl

200

tBuOK

HCl

NH

O

Cl

201

NR 2

CH 3

ClOC

NR 2

CH 3

1.

2. H 2

N

O

Cl

203 ; R = O

204 ;R = H

O

NH

N CH 3

O

Cl

O O CH 3

CH 3

CH 3

ClOCCH^3

NH

N

HO

Cl

O O

NaBH 4

206 207

202

205

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   (1986).


3. W.N. Chan, H.K.A. Morgan, M. Thompson, M. Evans, U.S. Patent 5,760,074
   (1998).


4. S.L. Kattiger, R.G. Naik, A.D. Lakdawalla, A.N. Dohadwalla, R.H. Rupp,
   N.J. de Souza, U.S. Patent 4,900,727 (1990).


5. R.G. Naik, B. Lal, R.H. Rupp, H.H. Sedlack, G. Dickneite, U.S. Patent
   5,284,856 (1994).


6. R.E. TenBrink, M.D. Ennis, R.A. Lahti, U.S. Patent 5,877,317 (1999).


7. M. Roe et al.,Bioorg. Med. Chem. Lett. 9 , 595 (1999).


8. C.J. Torrance, P.E. Jackson, E. Montgomery, A. Wissner, K.W. Kinzler,
   B. Vogelstein, P. Frost, C.M. Discafani,Nat. Med. 6 , 1024 (2000).

186 SIX-MEMBERED HETEROCYCLES FUSED TO ONE BENZENE RING