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US 11,753,392 B2Granted
Method for synthesis of deuterated amide and deuterated sulfonamide
AssigneeHinova Pharmaceuticals Inc.
InventorsWu Du, Kun Wen, Jinyun He, Haibo Li, Dekun Qin, Xinghai Li, Yuanwei Chen
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Abstract
A novel method for synthesizing deuterated amides and deuterated sulfonamides includes the following steps: (1) adding a compound M, DMAP, R3—X to a solvent to obtain a compound N after a reaction is complete; and (2) adding the compound N, R4—NH—R5, or a salt and base thereof to a solvent, and purifying after a reaction is complete to obtain a compound I.
Claims26
A method for synthesizing deuterated amine, comprising the steps of a first step of adding compound M, DMAP, and R3—X to a first solvent for reaction to obtain compound N;
- and
- a second step of adding compound N, R4—NH—R5 or a salt thereof, and a base to a second solvent for reaction to obtain a deuterated amine compound I,
- wherein:
- L is carbonyl or sulfonyl;
- R1 is
- R2 is selected from the group consisting of substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocyclic group, substituted or unsubstituted aryl, and substituted or unsubstituted heteroaryl;
- R3 is —CO—R6 or —SO2R7 and X is a leaving group,
- wherein, R6 and R7 are independently selected from alkoxy, alkyl, substituted alkyl, and aryl;
- R4 and R5 are independently selected from H, substituted or unsubstituted deuterated alkyl, deuterated cycloalkyl, deuterated heterocyclic group, deuterated aryl, and deuterated heteroaryl, with the proviso that R4 and R5 are not hydrogen at the same time;
- wherein, in the first step, a yield for the compound N thus synthesized is 92.3%, and
- wherein, in the second step, a yield for the deuterated amine compound I thus synthesized is 92.8%.
8 more elements
Dependencies are inferred from the claim text.