The efficient preparation method of a tedizolid intermediate includes the following steps: 1) subjecting 2-fluoro-4-substituted phenylacetic acid to a reaction with a Vilsmeier reagent, and adding a resulting reaction solution to an MX aqueous solution for quenching to obtain an intermediate shown in formula (II); and 2) subjecting the intermediate shown in formula (II) obtained in step 1) and 1-(2-methyl-2H-tetrazol-5-yl)ethanone to one-pot synthesis in the presence of an alkali and an ammonia source to obtain the intermediate shown in formula (I). In this method, a pyridine ring of the key intermediate shown in formula (I) is obtained through a ring-closing reaction of the 1-(2-methyl-2H-tetrazol-5-yl)ethanone and a Vinamidinium salt, and a key methyltetrazolyl group is introduced into the structure, which successfully avoids the use of highly-toxic sodium cyanide and sodium azide, the use of expensive palladium catalyst, and the use of methylation with low selectivity.

The efficient preparation method of a tedizolid intermediate includes the following steps: 1) subjecting 2-fluoro-4-substituted phenylacetic acid to a reaction with a Vilsmeier reagent, and adding a resulting reaction solution to an MX aqueous solution for quenching to obtain an intermediate shown in formula (II); and 2) subjecting the intermediate shown in formula (II) obtained in step 1) and 1-(2-methyl-2H-tetrazol-5-yl)ethanone to one-pot synthesis in the presence of an alkali and an ammonia source to obtain the intermediate shown in formula (I). In this method, a pyridine ring of the key intermediate shown in formula (I) is obtained through a ring-closing reaction of the 1-(2-methyl-2H-tetrazol-5-yl)ethanone and a Vinamidinium salt, and a key methyltetrazolyl group is introduced into the structure, which successfully avoids the use of highly-toxic sodium cyanide and sodium azide, the use of expensive palladium catalyst, and the use of methylation with low selectivity.

The efficient preparation method of a tedizolid intermediate includes the following steps: 1) subjecting 2-fluoro-4-substituted phenylacetic acid to a reaction with a Vilsmeier reagent, and adding a resulting reaction solution to an MX aqueous solution for quenching to obtain an intermediate shown in formula (II); and 2) subjecting the intermediate shown in formula (II) obtained in step 1) and 1-(2-methyl-2H-tetrazol-5-yl)ethanone to one-pot synthesis in the presence of an alkali and an ammonia source to obtain the intermediate shown in formula (I). In this method, a pyridine ring of the key intermediate shown in formula (I) is obtained through a ring-closing reaction of the 1-(2-methyl-2H-tetrazol-5-yl)ethanone and a Vinamidinium salt, and a key methyltetrazolyl group is introduced into the structure, which successfully avoids the use of highly-toxic sodium cyanide and sodium azide, the use of expensive palladium catalyst, and the use of methylation with low selectivity.

There is provided a process for the preparation of a compound of formula (I) as defined herein, wherein said process comprises reacting a compound of formula (II) as defined s herein with one or more suitable Vilsmeier reagent.

##STR00001##

There is provided a process for the preparation of a compound of formula (I) as defined herein, wherein said process comprises reacting a compound of formula (II) as defined s herein with one or more suitable Vilsmeier reagent.

##STR00001##

The present disclosure relates to the fields of chemistry and medicine, more particularly to processes for making 4-(2-chloro-4-methoxy-5-methylphenyl)-N-[(1S)-2-cyclopropyl-1-(3-fluoro-4-methylphenyl)ethyl]-5-methyl-N-prop-2-ynyl-1,3-thi-azol-2-amine (Compound 1), pharmaceutically acceptable salts, and crystalline forms thereof, for the treatment of congenital adrenal hyperplasia (CAH).

The present disclosure relates to the fields of chemistry and medicine, more particularly to processes for making 4-(2-chloro-4-methoxy-5-methylphenyl)-N-[(1S)-2-cyclopropyl-1-(3-fluoro-4-methylphenyl)ethyl]-5-methyl-N-prop-2-ynyl-1,3-thi-azol-2-amine (Compound 1), pharmaceutically acceptable salts, and crystalline forms thereof, for the treatment of congenital adrenal hyperplasia (CAH).

The present disclosure relates to using green solvents to synthesize an array of imines, imine-related and imine-derived compounds in an efficient and eco-friendly matter, satisfying green chemistry requirements. Reaction embodiments are performed using solvents, such as ethyl lactate and dimethyl isosorbide, which are both individually characterized as green. In embodiments, solvents include lactic whey and/or water as co-solvents. In these green solvents, the synthesis process discussed herein can produce up to quantitative yields of product at room temperature in a short duration. Embodiments include a method of forming an imine, imine-related or imine-derived compound product. In embodiments, the methods include mixing an aldehyde reactant with a nucleophilic/nitrogen-containing reactant in a green solvent at a temperature between negative twenty degrees Celsius (−20° C.) and positive fifty degrees Celsius (50° C.); stirring the mixture; and forming an imine, imine-related or imine-derived compound product.

The present disclosure relates to using green solvents to synthesize an array of imines, imine-related and imine-derived compounds in an efficient and eco-friendly matter, satisfying green chemistry requirements. Reaction embodiments are performed using solvents, such as ethyl lactate and dimethyl isosorbide, which are both individually characterized as green. In embodiments, solvents include lactic whey and/or water as co-solvents. In these green solvents, the synthesis process discussed herein can produce up to quantitative yields of product at room temperature in a short duration. Embodiments include a method of forming an imine, imine-related or imine-derived compound product. In embodiments, the methods include mixing an aldehyde reactant with a nucleophilic/nitrogen-containing reactant in a green solvent at a temperature between negative twenty degrees Celsius (−20° C.) and positive fifty degrees Celsius (50° C.); stirring the mixture; and forming an imine, imine-related or imine-derived compound product.

A method for manufacturing a compound comprising at least one imine group, the method comprising a step of reaction between a first compound comprising at least one amine group and a second compound comprising at least one carbonyl group, the reaction step being carried out in the presence of at least one supercritical fluid.