55402-04-5

Usage

InChI:InChI=1/C9H14O3/c1-4-11-9(12-5-2)7-6-8(3)10/h9H,4-5H2,1-3H3

Upstream product

• 18350-46-4 4-hydroxy-2-pentylacetaldehyde diethyl acetal 
• 10160-87-9 Propiolaldehyde diethyl acetal 
• 75-36-5 acetyl chloride 
• 81535-78-6 3,3-diethoxy-1-(tributylstannyl)prop-1-yne 
• 78191-00-1 N-Methoxy-N-methylacetamide 

Downstream Products

• 1400660-71-0 (S)-2-{[2-tert-butyl-5-(3-hydroxybenzylcarbamoyl)thiophen-2-carbonyl]amino}-3-[(thiophene-2-carbonyl)amino]propionic acid 
• 1400663-13-9 C₂₆H₂₇N₃O₈S 
• 1400663-12-8 C₂₄H₂₅N₃O₆S₂ 
• 1400663-11-7 C₂₇H₂₇N₃O₈S 
• 1400663-10-6 C₂₆H₂₅N₅O₆S 
• 1400663-09-3 C₂₃H₂₃N₅O₇S 
• 1400663-08-2 C₂₆H₂₅N₅O₆S 
• 1400663-07-1 C₂₅H₂₇N₅O₈S 
• 1400663-06-0 C₂₆H₂₅N₅O₆S 
• 1400663-05-9 C₂₃H₂₃N₅O₆S 
• 1400663-04-8 C₂₅H₂₅N₃O₇S 
• 1400663-03-7 C₂₃H₂₃N₅O₈S 
• 1400663-02-6 C₂₅H₂₅N₃O₈S 
• 1400663-01-5 C₂₄H₂₅N₃O₆S₂ 

Relevant academic research and scientific papers

Highly flexible and efficient synthesis of the GABAB enhancer 4-(2-hexylsulfanyl-6-methyl-pyrimidin-4-ylmethyl)-morpholine

In the course of establishing a flexible synthesis of 2,4,6-substituted pyrimidines, we discovered that 2-hexyl-isothiourea hydrobromide reacts at ambient temperature and in a mildly exothermic fashion with 5,5-diethoxy-pent-3-yn-2-one upon treatment with 2 equiv of triethylamine in tetrahydrofuran to afford 4-diethoxymethyl-2-hexylsulfanyl-6-methyl-pyrimidine in 80% isolated yield. The methodology was developed in the search for an improved synthesis of the GABAB enhancer 4-(2-hexylsulfanyl-6-methyl-pyrimidin-4-ylmethyl)-morpholine.

THIAZOLE AND THIOPHENE COMPOUNDS

Provided herein are compounds of the formula (I): as well as pharmaceutically acceptable salts thereof, wherein the substituents are as those disclosed in the specification. These compounds, and the pharmaceutical compositions containing them, are useful for the treatment of inflammatory diseases and disorders such as, for example, asthma and COPD

4-(Isoxazol-3-yl)pyrimidines from pyrimidinyl nitrile oxides

The 1,3-dipolar cycloaddition reaction of pyrimidinylaldoxime derived nitrile oxides and alkynes delivers 4-(isoxazol-3-yl)pyrimidines. The procedures reported accommodate three points of diversification around this bisheterocyclic scaffold and the resulting library of compounds has been added to the National Institutes of Health repository (ca. 10 mg of each with >90% purity) for pilot-scale biomedical studies with bioassay data available at the National Center for Biotechnology Information PubChem database. Georg Thieme Verlag Stuttgart.

Aminomethylpyrimidines as allosteric enhancers of the GABAB receptors

The present invention relates to compounds of formula whereinX is —S— or —NH—; R3/R4 together with the N-atom to which they are attached form a non aromatic 5, 6 or 7 membered ring, which optionally contains in addition to the N-atom one additional heteroatom selected from the group consisting of O, S and N, and wherein the ring is optionally substituted by hydroxy, lower alkyl, lower alkoxy, —NR2, —CONR2, —CO-lower alkyl or benzyl; or R3/R4 form together with the N-atom to which they are attached a heterocyclic ring system, containing two or three rings and which optionally contains one or two additional heteroatoms selected from the group consisting of N and O and which has no more than 20 carbon atoms; and R, R1, R2, and R5 are as defined herein and to pharmaceutically suitable acid addition salts thereof. It has been found that the compounds of the invention are active on the GABAB receptor and therefore are useful for the treatment of anxiety, depression, epilepsy, schizophrenia, cognitive disorders, spasticity and skeletal muscle rigidity, spinal cord injury, multiple sclerosis, amyotrophic lateral sclerosis, cerebral palsy, neuropathic pain and craving associated with cocaine and nicotine, psychosis, panic disorder, posttraumatic stress disorders and gastro-intestinal disorders.

4- (SULFANYL-PYRIMIDIN-4-YLMETHYL) -MORPHOLINE DERIVATIVES AND RELATED COMPOUNDS AS GABA RECEPTOR LIGANDS FOR THE TREATMENT OF ANXIETY, DEPRESSION AND EPILEPSY

The present invention relates to compounds of Formula (I) wherein X is-S-or-NH-; R1 is alkyl, alkenyl, arylalkyl, arylalkenyl or aryl-O-alkyl, wherein the aryl groups are optionally substituted by one or more substituents, selected from the group consisting of lower alkyl, lower alkoxy, halogen or lower halogen-alkyl; R2 is hydrogen, lower alkyl or cycloalkyl; R3 /R4 may form together with the N-atom to which they are attached a non aromatic5, 6 or 7 membered ring, which may contain in addition to the N-atom one additional heteroatom selected from the group consisting of O, S or N, and wherein the ring is optionally substituted by hydroxy, lower alkyl, lower alkoxy,-NR2,-CONR2,-CO-lower alkyl or benzyl; or may form together with the N-atom to which they are attached a heterocyclic ring system, containing at least two rings and which may contain one or two additional heretoatoms, selected from the group consisting of N or O; R is hydrogen or lower alkyl; R5 is hydrogen or lower alkyl; and to pharmaceutically suitable acid addition salts thereof. It has been found that the compounds are active on the GABAB receptor and therefore useful for the treatment of anxiety, depression, epilepsy, schizophrenia, cognitive disorders, spasticity and skeletal muscle rigidity, spinal cord injury, multiple sclerosis, amyotrophic lateral sclerosis, cerebral palsy, neuropathic pain and craving associated with cocaine and nicotine, psychosis, panic disorder, posttraumatic stress disorders or gastro-intestinal disorders.

4-Hydroxynon-2-enal, a cytotoxic lipid peroxidation product, and its C5- analog 4-hydroxypent-2-enal: Enantioselective synthesis and stereoanalysis

A stereoselective synthesis of the lipid peroxidation products 4- hydroxypent-2-enal (1a) and 4-hydroxynon-2-enal (1b) in high optical purity is presented. The configuration of 1a and b was established by Ru(III)- catalyzed oxidative degradation and subsequent stereoanalysis of the resulting α-hydroxy acids. It was demonstrated that 1a is configuratively stable under physiological conditions.

Preparation d'acetals fonctionnels

Functional acetals can be prepared either by reaction of functional organomagnesium compounds with the mixed orthoformate C6H5O-CH()C2H5)2 or by reaction of carbonyl compounds with the acetylenic lithium compounds Li-CC-(CH2)n-CH(OC2H5)2 (n=0,1).

Palladium-Catalyzed Reactions of Acyl Chlorides with (1-Alkynyl)tributylstannanes. A Convenient Synthesis for 1-Alkynyl Ketones

Acyl chlorides couple with (1-alkynyl)tributylstannanes in the presence of catalytic amounts of palladium(II) or palladium(0) complexes to produce 1-alkynyl ketones in respectable yields.The couplings of isobutyryl, acetyl, benzoyl, and p-nitrobenzoyl chlorides with phenylethynyl-, (trimethylsilyl)ethynyl-, (carbomethoxy)ethynyl-, -1-propynyl>-, and (3,3-diethoxy-1-propynyl)tributylstannanes were investigated in the presence of tetrakis(triphenylphosphine)palladium(O), benzylchlorobis(triphenylphosphine)palladium(II), dichlorobis(triphenylphosphine)palladium(II), or phenyliodobis(triphenylphosphine)palladium(II).The reactions are highly selective in that only the alkynyl groups are transferred from the stannane.