518047-40-0

Basic information

• Product Name: tert-butyl 3-cyanomorpholine-4-carboxylate
• Synonyms: tert-butyl 3-cyanomorpholine-4-carboxylate;N-Boc-3-cyanomorpholine;4-Boc-3-cyanomorpholine;3-Cyano-4-morpholinecarboxylic acid tert-butyl ester;4-Morpholinecarboxylic acid, 3-cyano-, 1,1-diMethylethyl ester;3-Cyano-Morpholine-4-carboxylicacidtert-butylester
• CAS NO: 518047-40-0
• Molecular Formula: C₁₀H₁₆N₂O₃
• Molecular Weight: 212.24564
• Mol File: 518047-40-0.mol
• Article Data: 7

Chemical Properties

• Melting Point: 100-101℃
• Boiling Point: 340℃
• Flash Point: 160℃
• Appearance: /
• Density: 1.13
• Refractive Index: 1.488
• Storage Temp.: 2-8°C
• CAS DataBase Reference: tert-butyl 3-cyanomorpholine-4-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: tert-butyl 3-cyanomorpholine-4-carboxylate(518047-40-0)
• EPA Substance Registry System: tert-butyl 3-cyanomorpholine-4-carboxylate(518047-40-0)

Safety Data

• Hazardous Substances Data: 518047-40-0(Hazardous Substances Data)

Usage

Description

Tert-butyl 3-cyanomorpholine-4-carboxylate is an organic compound that serves as a key intermediate in the synthesis of various pharmaceuticals. It is characterized by its structural features, which include a morpholine ring with a cyano group and a carboxylate group, as well as a tert-butyl group that provides steric hindrance. This unique structure makes it a valuable building block in the development of new drugs and therapeutic agents.

Uses

Used in Pharmaceutical Industry:
Tert-butyl 3-cyanomorpholine-4-carboxylate is used as a reactant for the synthesis of HIV integrase inhibitors. These inhibitors play a crucial role in the treatment of HIV by blocking the integration of the viral DNA into the host's genome, thereby preventing the replication and spread of the virus. tert-butyl 3-cyanomorpholine-4-carboxylate's structural properties make it an ideal candidate for the development of potent and selective integrase inhibitors, which can be further optimized for improved efficacy and safety.

InChI:InChI=1/C10H16N2O3/c1-10(2,3)15-9(13)12-4-5-14-7-8(12)6-11/h8H,4-5,7H2,1-3H3

Upstream product

• 518047-39-7 tert-butyl 3-(aminocarbonyl)morpholine 4-carboxylate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 97039-63-9 morpholine-3-carbonitrile 
• 212650-43-6 4-(tert-butoxycarbonyl)morpholine-3-carboxylic acid 
• 19158-51-1 P-toluenesulfonyl cyanide 
• 220199-85-9 morpholine-4-carboxylic acid tert-butyl ester 
• 7677-24-9 trimethylsilyl cyanide 
• 195964-53-5 tert-butyl 3-methoxymorpholine-4-carboxylate 

Downstream Products

• 518058-62-3 tert-butyl 3-[amino(hydroxyimino)methyl]morpholine-4-carboxylate 
• 519030-38-7 N-(4-fluorobenzyl)-5,6-dihydroxy-2-(morpholin-3-yl)pyrimidine-4-carboxamide 
• 518058-62-3 tert-butyl 3-[amino(hydroxyimino)methyl]morpholine-4-carboxylate 
• 475106-18-4 tert‐butyl N‐[(morpholin‐3‐yl)methyl]carbamate 
• 66937-99-3 morpholine-3-carboxylic acid hydrochloride 

Relevant articles and documents

C(sp3)?H Cyanation Promoted by Visible-Light Photoredox/Phosphate Hybrid Catalysis

Inspired by the reaction mechanism of photo-induced DNA cleavage in nature, a C(sp3)?H cyanation reaction promoted by visible-light photoredox/phosphate hybrid catalysis was developed. Phosphate radicals, generated by one-electron photooxidation of phosphate salt, functioned as a hydrogen-atom-transfer catalyst to produce nucleophilic carbon radicals from C(sp3)?H bonds with a high bond-dissociation energy. The resulting carbon radicals were trapped by a cyano radical source (TsCN) to produce the C?H cyanation products. Due to the high functional-group tolerance and versatility of the cyano group, the reaction will be useful for realizing streamlined building block syntheses and late-stage functionalization of drug-like molecules.

Photoinduced direct cyanation of C(sp3)-H bonds

A general and practical synthetic protocol for the direct transformation of unreactive C(sp3)-H bonds to C(sp3)-CN bonds has been developed. The homolytic cleavage of the C-H bond is initiated by photo-excited benzophenone, and the resulting carbon radical subsequently reacts with tosyl cyanide to afford the corresponding nitrile in a highly efficient manner. The present methodology is widely applicable to various starting materials including ethers, alcohols, amine derivatives, alkanes, and alkylbenzenes. This newly developed C-H cyanation protocol provides a powerful tool for selective one-carbon elongation for the construction of architecturally complex molecules. Georg Thieme Verlag Stuttgart - New York.

Dihydroxypyrimidine-4-carboxamides as novel potent and selective HIV integrase inhibitors

Human immunodeficiency virus type-1 (HIV-1) integrase, one of the three constitutive viral enzymes required for replication, is a rational target for chemotherapeutic intervention in the treatment of AIDS that has also recently been confirmed in the clinical setting. We report here on the design and synthesis of N-benzyl-5,6-dihydroxypyrimidine-4-carboxamides as a class of agents which exhibits potent inhibition of the HIV-integrase-catalyzed strand transfer process. In the current study, structural modifications on these molecules were made in order to examine effects on HIV-integrase inhibitory potencies. One of the most interesting compounds for this series is 2-[1-(dimethylamino)-1-methylethyl]-N-(4-fluorobenzyl)-5,6-dihydroxypyrimidine- 4-carboxamide 38, with a CIC95 of 78 nM in the cell-based assay in the presence of serum proteins. The compound has favorable pharmacokinetic properties in preclinical species (rats, dogs, and monkeys) and shows no liabilities in several counterscreening assays, highlighting its potential as a clinically useful antiviral agent.