Patent ID: 7968721

Claim:
A process for preparing a selective androgen receptor modulator (SARM) compound represented by the structure of formula 1: wherein X is O; T is OH, OR, NHCOCH 3 , or NHCOR; Z is NO 2 , CN, COOH, COR, NHCOR or CONHR; Y is CF 3 , F, I, Br, Cl, CN, C(R) 3 or Sn(R) 3 ; Q is alkyl, halogen, CF 3 , CN C(R) 3 , Sn(R) 3 , N(R) 2 , NHCOCH 3 , NHCOCF 3 , NHCOR, NHCONHR, NHCOOR, OCONHR, CONHR, NHCSCH 3 , NHCSCF 3 , NHCSR, NHSO 2 CH 3 , NHSO 2 R, OR, COR, OCOR, OSO 2 R, SO 2 R, SR; or Q together with the benzene ring to which it is attached is a fused ring system represented by structure A, B or C: R is alkyl, haloalkyl, dihaloalkyl, trihaloalkyl, CH 2 F, CHF 2 , CF 3 , CF 2 CF 3 , aryl, phenyl, halogen, alkenyl or OH; and R 1 is CH 3 , CH 2 F, CHF 2 , CF 3 , CH 2 CH 3 , or CF 2 CF 3 ; said process comprising the steps of: coupling an amide of formula II: wherein Z, Y, R 1 and T are as defined above and L is a leaving group, with a compound of formula III: wherein Q and X are as defined above, producing said compound of formula I; and a purification step consisting of precipitating said compound of formula (1) in a mixture of alcohol and water alone.