147402-52-6

Basic information

• Product Name: Isoxazole, 3-methyl-5-(2S)-2-pyrrolidinyl- (9CI)
• Synonyms: Isoxazole, 3-methyl-5-(2S)-2-pyrrolidinyl- (9CI)
• CAS NO: 147402-52-6
• Molecular Formula: C₈H₁₂N₂O
• Molecular Weight: 152.19368
• Product Categories: OXAZOLE
• Mol File: 147402-52-6.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 267.7±28.0 °C(Predicted)
• Appearance: /
• Density: 1.077±0.06 g/cm3(Predicted)
• PKA: 8.74±0.10(Predicted)
• CAS DataBase Reference: Isoxazole, 3-methyl-5-(2S)-2-pyrrolidinyl- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Isoxazole, 3-methyl-5-(2S)-2-pyrrolidinyl- (9CI)(147402-52-6)
• EPA Substance Registry System: Isoxazole, 3-methyl-5-(2S)-2-pyrrolidinyl- (9CI)(147402-52-6)

Safety Data

• Hazardous Substances Data: 147402-52-6(Hazardous Substances Data)

Upstream product

• 5211-23-4 N-carbobenzyloxy-L-proline methyl ester 
• 124-63-0 methanesulfonyl chloride 
• 130419-38-4 (S)-2-(2,2-dibromoethenyl)-1-pyrrolidinecarboxylic acid 1,1-dimethylethyl ester 
• 130418-90-5 (S)-tert-butyl 2-ethynylpyrrolidine-1-carboxylate 
• 69610-41-9 Boc-L-Pro-H 
• 69610-40-8 N-(tert-butoxycarbonyl)-L-prolinol 
• 15761-39-4 1-(tert-butoxycarbonyl)-L-proline 
• 147402-51-5 (S)-3-methyl-5-<1-(tert-butoxycarbonyl)-pyrrolidinyl>isoxazole 

Downstream Products

• 147402-53-7 (S)-3-methyl-5-(1-methyl-2-pyrrolidinyl)isoxazole 
• 1369958-89-3 ((R)-7-(3,4-dichlorophenyl)-5-(methoxymethyl)-4,7-dihydropyrazolo[1,5-a]pyrimidin-6-yl)((S)-2-(3-methylisoxazol-5-yl)pyrrolidin-1-yl)methanone 
• 1369958-94-0 ((R)-7-(3,4-dichlorophenyl)-2,5-dimethyl-4,7-dihydropyrazolo[1,5-a]pyrimidin-6-yl)((S)-2-(3-methylisoxazol-5-yl)pyrrolidin-1-yl)methanone 
• 1369958-95-1 ((R)-7-(3,4-dichlorophenyl)-5-methyl-2-(trifluoromethyl)-4,7-dihydropyrazolo[1,5-a]pyrimidin-6-yl)((S)-2-(3-methylisoxazol-5-yl)pyrrolidin-1-yl)methanone 
• 1219833-07-4 ((R)-7-(3,4-dichlorophenyl)-5-methyl-4,7-dihydropyrazolo-[1,5-a]pyrimidin-6-yl)((S)-2-(3-methylisoxazol-5-yl)pyrrolidin-1-yl)methanone 
• 1369959-28-3 ((S)-2-cyclopropyl-7-(3,4-dichlorophenyl)-5-methyl-4,7-dihydropyrazolo[1,5-a]pyrimidin-6-yl)((S)-2-(3-methylisoxazol-5-yl)pyrrolidin-1-yl)methanone 
• 1369958-96-2 ((R)-2-cyclopropyl-7-(3,4-dichlorophenyl)-5-methyl-4,7-dihydropyrazolo[1,5-a]pyrimidin-6-yl)((S)-2-(3-methylisoxazol-5-yl)pyrrolidin-1-yl)methanone 
• 935746-16-0 C₂₃H₃₀FN₃O₄ 

Relevant articles and documents

Discovery of ((S)-5-(methoxymethyl)-7-(1-methyl-1 H -indol-2-yl)-2- (trifluoromethyl)-4,7-dihydropyrazolo[1,5- a ]pyrimidin-6-yl)((S)-2-(3- methylisoxazol-5-yl)pyrrolidin-1-yl)methanone as a potent and selective I Kur inhibitor

Previously disclosed dihydropyrazolopyrimidines are potent and selective blockers of IKur current. A potential liability with this chemotype is the formation of a reactive metabolite which demonstrated covalent binding to protein in vitro. When substituted at the 2 or 3 position, this template yielded potent IKur inhibitors, with selectivity over hERG which did not form reactive metabolites. Subsequent optimization for potency and PK properties lead to the discovery of ((S)-5-(methoxymethyl)-7-(1-methyl-1H-indol- 2-yl)-2-(trifluoromethyl)-4,7-dihydropyrazolo[1,5-a]pyrimidin-6-yl)((S) -2-(3-methylisoxazol-5-yl)pyrrolidin-1-yl)methanone (13j), with an acceptable PK profile in preclinical species and potent efficacy in the preclinical rabbit atrial effective refractory period (AERP) model.

4-(PYRAZOL-3-YLAMINO) PYRIMIDINE DERIVATIVES FOR USE IN THE TREATMENT OF CANCER

A compound of Formula (I); wherein the substituents are as defined in the text for use in modulating insulin-like growth factor 1 receptor activity in a warm blooded animal such as man.

Synthesis and 11C-labelling of two selective high affinity nicotinic cholinergic agonists for evaluation as radioligands for PET studies

ABT-418 ((S)-3-methyl-5-[1-methyl-2-pyrrolidinyl]isoxazole) and N-methylcytisine (N-methyl- 1,2,3,4,5,6-hexahydro-1,5-methano-8H-pyrido-[1,2-a][1,5]diazocin-8-one) are two high affinity nicotinic cholinergic agonists. ABT-418 was synthesized in 7 steps from commercially available (S)-Boc- proline in 35% overall yield. Methylation of commercial cytisine cleanly gave N-methyl-cytisine. ABT-418 and N-methylcytisine were labelled using [11C]methyl iodide by methylation of the corresponding nor-precursors for their in vivo evaluation as positron emission tomography (PET) probes of the nicotinic cholinergic receptors in baboon brain. As for [11C]nicotine, specific binding in vivo could not be demonstrated for ABT-418. Therefore, further experiments are needed to determine the full PET pharmacological profile and the subsequent potential clinical applications of ABT-418 as a tracer for PET experiments. For labelled N-methyl-cytisine, radioactivity in the cerebral cortex and in tile blood were similar. Thus, 11C-labelled N-methylcytisine does not appear to be a suitable ligand for mapping brain nAChR.