97039-63-9

Usage

InChI:InChI=1/C5H8N2O/c6-3-5-4-8-2-1-7-5/h5,7H,1-2,4H2

Upstream product

• 110-91-8 morpholine 
• 7677-24-9 trimethylsilyl cyanide 
• 151-50-8 potassium cyanide 
• 81684-86-8 dodecahydrotris([1,4]oxazino)[4,3-a:4',3'-c:4'',3''-e][1,3,5]triazine 
• 773837-37-9 sodium cyanide 

Downstream Products

• 518047-40-0 tert-butyl 3-cyanomorpholine-4-carboxylate 
• 66937-99-3 morpholine-3-carboxylic acid hydrochloride 

Relevant academic research and scientific papers

Preparation method N-t-butyloxycarboryl morpholine-3-carboxylic acid

The invention provides a preparation method of N-t-butyloxycarboryl morpholine-3-carboxylic acid. According to the preparation method, 1,2-epoxypropane is taken as a raw material, ring-opening reaction, cyclization reaction, hydrolysis reaction, and nitrogen protection reaction are carried out successively so as to obtain N-t-butyloxycarboryl morpholine-3-carboxylic acid, wherein the ring-openingreaction is carried out under catalytic effect of transition metal Lewis acid. Reaction conditions are mild; operation is simple; no severely toxic side product is generated; the reaction yield of each step is 80% or higher; the reaction yield of a part reaction steps is 90% or higher; the yield is high; the preparation method is beneficial for large scale production, and is high in market value.

Preparation method for morpholine-3-carboxylic acid

The invention provides a preparation method for morpholine-3-carboxylic acid. The preparation method comprises the following steps: taking (2-Hydroxyethyl)carbamic acid tert-butyl ester and 2-chloroacrylonitrile as raw materials, performing Michael addition reaction, performing deprotection reaction, performing ring-closure reaction, and performing hydrolysis reaction to obtain the morpholine-3-carboxylic acid. The preparation method for the morpholine-3-carboxylic acid provided by the invention is used for preparing morpholine-3-carboxylic acid through Michael addition reaction, the deprotection reaction, ring-closure reaction and hydrolysis reaction; the whole preparation process is simple, is fewer in steps, adopts cheap and easily available raw materials, is free of stimulus and easilyallergic substances, and avoids generating highly toxic products and side products; and the yield of reaction at each step can be 80% or higher, the total yield is high, large-scale production is facilitated, economic benefits are improved, and the market value is good.

Photoredox-Catalyzed Cα-H Cyanation of Unactivated Secondary and Tertiary Aliphatic Amines: Late-Stage Functionalization and Mechanistic Studies

This paper describes the development and mechanistic studies of a general, high-yielding amine Cα-H cyanation protocol via photoredox catalysis. Inexpensive NaCN is employed as the cyanide source and air is the external oxidant, resulting in mild and highly functional group tolerant conditions. Notably, efficient Cα-H cyanations of secondary and tertiary aliphatic amines and of complex, biologically active compounds (drugs) can be performed using the established methodology. Mechanistic studies suggest that the carboxylic acid additive has three effects: formation of a stabilizing hemiaminal intermediate, prevention of catalyst decomposition by protonating the substrate, and modulation of fluorescence quenching of the photoexcited catalyst species.

Discovery and synthesis of HIV integrase inhibitors: Development of potent and orally bioavailable N-methyl pyrimidones

The human immunodeficiency virus type-1 (HIV-1) encodes three enzymes essential for viral replication: a reverse transcriptase, a protease, and an integrase. The latter is responsible for the integration of the viral genome into the human genome and, therefore, represents an attractive target for chemotherapeutic intervention against AIDS. A drug based on this mechanism has not yet been approved. Benzyl-dihydroxypyrimidine-carboxamides were discovered in our laboratories as a novel and metabolically stable class of agents that exhibits potent inhibition of the HIV integrase strand transfer step. Further efforts led to very potent compounds based on the structurally related N-Me pyrimidone scaffold. One of the more interesting compounds in this series is the 2-N-Me-morpholino derivative 27a, which shows a CIC95 of 65 nM in the cell in the presence of serum. The compound has favorable pharmacokinetic properties in three preclinical species and shows no liabilities in several counterscreening assays.

Preparation of 5-hydroxy-6-oxo-1,6-dihydropyrimidine compounds

5-Hydroxy-6-oxo-1,6-dihydropyrimidine compounds are prepared by the condensation of dihydroxyfumarate derivatives with amidines. The pyrimidine compounds are useful as intermediates in the preparation of pharmacologically active compounds.

OXYDATION OF SECONDARY AMINES TO α-CYANOAMINES

The dehydrogenation of secondary amines with phenylseleninic anhydride or acid under mild conditions in the presence of either sodium cyanide or trimethylsilylcyanide gives good yields of α-cyanoamines.These compounds can be regarded as protected imines, or as a source of α-amino-acids.