Patent ID: 11919868
Assignee: RECURSION PHARMACEUTICALS, INC.
Field: Organic fine chemistry (Chemistry)
Classification: CPC A  C  Y | IPC A  C

Claim 14:
15. A method of making a compound of claim 1 or a stereoisomer, a tautomer, or a pharmaceutically acceptable salt thereof according to Schemes 1 or 2 below:, , wherein m, X1, X2, X3, X4, X5, R1, R2, R3, R4, R5, and R6 areas defined in claim 1, and
wherein for Scheme I:
joining intermediate 1 with intermediate 2 through a reductive amination to give intermediate 3;
amide coupling intermediate 3 with carboxylic acid 4 to give amide 5;
reducing amide 5 to give diazepinedione 6;
hydrolyzing diazepinedione 6 to yield carboxylic acid 7;
amide coupling amine intermediate 8 with carboxylic acid 7 to yield product I;

and wherein for Scheme II:
amide coupling of amine intermediate 8 with carboxylic acid 9 to yield intermediate 10;
vinylation of intermediate 10, followed by oxidative cleavage to give aldehyde intermediate 11;
joining intermediate 11 with intermediate 2 to give intermediate 12;
amide coupling of intermediate 12 with carboxylic acid 4 to give amide 13; and
reducing amide 13 to yield product I.