Submission Details
Molecule(s):
CC(=O)NCCN1CCC(CNS(C)(=O)=O)(CC(=O)Nc2cnccc2C)CC1
Design Rationale:
By eye, docking. Saturate the benzene ring in x0104 and form a bond to the proximal carbon of x0107. Delete the pyrrole and fluorine of x0104 to reduce complexity. Move amidoethyl side chain of x0104 to 6-ring. Change the 6-ring from a cyclohexane to a piperidine to get away from stereochemical problems.
Other Notes:
Proposed synthesis starts from CAS 91419-52-2 (widely available). 1 a) LDA, b) ethylbromoacetate; 2 Raney Ni, H2 gives spirocyclic lactam; 3 open the lactam with requisite amine; 4 sulfonylation; 5 Boc deprotection; 6 alkylation with 2-bromoethylamine; 7 acylation. Aminoethyl group can be switched to aminopropyl by doing step 6 with acrylonitrile followed by reduction. Numerous analogues possible.