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US 10,081,610 B2Granted
Efficient and scalable synthesis of 2-(1′h-indole-3′-carbonyl)-thiazole-4-carboxylic acid methyl ester and its structural analogs
AssigneeAriagen, Inc.
InventorsJiasheng Song, Suoming Zhang, Guodong Li, Luquing Yang
Life of this patent
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Abstract
Methods of synthesizing 2-(1′H-indole-3′-carbonyl)-thiazole-4-carboxylic acid methyl ester (ITE) and structural analogs thereof. The methods include condensation reactions or condensation and oxidation reactions to form the thiazoline or thiazole moiety of ITE or its structural analogs.
Claims25
A method of synthesizing a compound comprising condensing a compound of Formula II with a compound of Formula III to yield a compound of Formula IV, wherein:
- Formula II is:
- or a salt thereof;
- Formula III is:
- or a salt thereof;
- Formula IV is:
- or a salt thereof;
- W, Y, and Z are each independently selected from the group consisting of oxygen (O) and sulfur (S);
- and
- R1, R2, R3, R4, R5, R6, R7, and RN are each independently selected from the group consisting of hydrogen, deuterium, halo, amino, hydroxy, cyano, formyl, nitro, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, alkoxy, haloalkoxy, thioalkoxy, halothioalkoxy, alkanoyl, haloalkanoyl, thioalkanoyl, halothioalkanoyl, carbonyloxy, halocarbonyloxy, carbonylthio, halocarbonylthio, thiocarbonyloxy, halothiocarbonyloxy, thiocarbonylthio, halothiocarbonylthio, and —S(O)nR8 (n=0 to 2, R8 is directly connected to S), wherein R8 is selected from the group consisting of hydrogen, deuterium, halo, amino, hydroxy, thiol, cyano, formyl, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, alkoxy, haloalkoxy, thioalkoxy, halothioalkoxy, alkanoyl, haloalkanoyl, thioalkanoyl, halothioalkanoyl, carbonyloxy, halocarbonyloxy, carbonylthio, halocarbonylthio, thiocarbonyloxy, halothiocarbonyloxy, thiocarbonylthio, and halothiocarbonylthio.
6 more elements
A method of synthesizing a compound comprising condensing a compound of Formula V with a compound of Formula VI to yield a compound of Formula I, wherein:
- Formula V is:
- or a salt thereof;
- Formula VI is:
- or a salt thereof;
- Formula I is:
- or a salt thereof;
- X is a leaving group;
- W, Y, and Z are each independently selected from the group consisting of oxygen (O) and sulfur (S);
- and
- R1, R2, R3, R4, R5, R6, R7, and RN are each independently selected from the group consisting of hydrogen, deuterium, halo, amino, hydroxy, cyano, formyl, nitro, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, alkoxy, haloalkoxy, thioalkoxy, halothioalkoxy, alkanoyl, haloalkanoyl, thioalkanoyl, halothioalkanoyl, carbonyloxy, halocarbonyloxy, carbonylthio, halocarbonylthio, thiocarbonyloxy, halothiocarbonyloxy, thiocarbonylthio, halothiocarbonylthio, and —S(O)nR8 (n=0 to 2, R8 is directly connected to S), wherein R8 is selected from the group consisting of hydrogen, deuterium, halo, amino, hydroxy, thiol, cyano, formyl, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, alkoxy, haloalkoxy, thioalkoxy, halothioalkoxy, alkanoyl, haloalkanoyl, thioalkanoyl, halothioalkanoyl, carbonyloxy, halocarbonyloxy, carbonylthio, halocarbonylthio, thiocarbonyloxy, halothiocarbonyloxy, thiocarbonylthio, and halothiocarbonylthio;
- and
- wherein the condensing is conducted in a protic solvent.
9 more elements
Dependencies are inferred from the claim text.