162045-30-9

Basic information

• Product Name: tert-butyl 4-(2-oxo-2H-benzo[d][1,3]oxazin-1(4H)-yl)piperidine-1-carboxylate
• Synonyms: tert-butyl 4-(2-oxo-2H-benzo[d][1,3]oxazin-1(4H)-yl)piperidine-1-carboxylate;Tert-Butyl4-(2-Oxo-2,4-Dihydro-1H-Benzo[D][1,3]Oxazin-1-Yl)Piperidine-1-Carboxylate;N-Boc-1-(4-piperidinyl)-1,2-dihydro-4H-3,1-benzoxazin-2-one;4-(2-Oxo-2H-3,1-benzoxazin-1(4H)-yl)-1-piperidinecarboxylic acid 1,1-dimethylethyl ester;tert-butyl 4-(2-oxo-4H-3,1-benzoxazin-1-yl)piperidine-1-carboxylate
• CAS NO: 162045-30-9
• Molecular Formula: C₁₈H₂₄N₂O₄
• Molecular Weight: 332.39416
• Mol File: 162045-30-9.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 449.2±45.0 °C(Predicted)
• Appearance: /
• Density: 1.216±0.06 g/cm3(Predicted)
• PKA: 0.77±0.20(Predicted)
• CAS DataBase Reference: tert-butyl 4-(2-oxo-2H-benzo[d][1,3]oxazin-1(4H)-yl)piperidine-1-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: tert-butyl 4-(2-oxo-2H-benzo[d][1,3]oxazin-1(4H)-yl)piperidine-1-carboxylate(162045-30-9)
• EPA Substance Registry System: tert-butyl 4-(2-oxo-2H-benzo[d][1,3]oxazin-1(4H)-yl)piperidine-1-carboxylate(162045-30-9)

Safety Data

• Hazardous Substances Data: 162045-30-9(Hazardous Substances Data)

Usage

General Description

Tert-butyl 4-(2-oxo-2H-benzo[d][1,3]oxazin-1(4H)-yl)piperidine-1-carboxylate is a synthetic chemical compound with a complex and specific molecular structure. It is a ester of tert-butyl and carboxylic acid, containing a piperidine ring with an attached oxo-benzo[d][1,3]oxazine moiety. tert-butyl 4-(2-oxo-2H-benzo[d][1,3]oxazin-1(4H)-yl)piperidine-1-carboxylate is primarily used as an intermediate in the synthesis of pharmaceuticals and other organic compounds. It has potential applications in medicinal chemistry, where it can be used to create diverse molecules with biological activity. Due to its intricate structure and potential uses in drug development, tert-butyl 4-(2-oxo-2H-benzo[d][1,3]oxazin-1(4H)-yl)piperidine-1-carboxylate may be of interest to researchers and scientists in the field of organic chemistry and pharmacology.

Upstream product

• 179323-66-1 1-tert-butoxycarbonyl-4-[(2-hydroxymethyl)phenylamino]piperidine 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 162045-29-6 1-(tert-Butoxycarbonyl)-4-[(2-hydroxymethylphenyl)amino]piperidine 
• 79099-07-3 N-tert-butyloxycarbonylpiperidin-4-one 
• 5344-90-1 2-Aminobenzyl alcohol 

Downstream Products

• 162042-41-3 4-{3-Methoxy-4-[4-(2-oxo-4H-benzo[d][1,3]oxazin-1-yl)-piperidine-1-carbonyl]-phenoxy}-piperidine-1-carboxylic acid tert-butyl ester 
• 208516-94-3 1-[1-(5-Fluoro-4-hydroxy-2-methoxy-benzoyl)-piperidin-4-yl]-1,4-dihydro-benzo[d][1,3]oxazin-2-one 
• 181269-53-4 1-(1-(4-(N-tert-butyloxycarbonyl-4-piperidinyloxy)-5-fluoro-2-methoxy-benzoyl)-piperidin-4-yl)-4H-3,1-benzoxazin-2(1H)-one 
• 208517-38-8 1-(1-{2-methoxy-4-[1-(2-methylpyridin-3-ylcarbonyl)piperidin-4-yloxy]benzoyl}piperidin-4-yl)-1,4-dihydrobenz[d][1,3]oxazin-2-one 

Relevant articles and documents

Synthesis of new benzoxazinone derivatives as neuropeptide Y5 antagonists for the treatment of obesity

Screening of our internal chemical collection against the neuropeptide Y5 (NPY Y5) receptor allowed the identification of a benzoxazine derivative 5f as a hit that showed moderate affinity (IC50 = 300 nM). With the aim of improving the in vitro potency, a series of 2-benzoxazinone derivatives have been synthesized and tested for NPY Y5 activity. Most of the compounds were found to be potent and selective NPY Y5 antagonists having nanomolar binding affinities for the NPY Y5 receptor and showing functional antagonism in the forskolin-induced cyclic AMP test. Prelimminary studies in order to understand the structure-activity relationship were undertaken. Selected compounds were further evaluated for in vivo efficacy, affording the lead compound 2-[4-(8-methyl-2-oxo-4H-benzo[d][1,3]oxazin-1-yl)piperidin-1-yl] -N-(9-oxo-9H-fluoren-3-yl)acetamide 5p, which displayed in vivo activity reducing food intake in rodents.

Development of orally active oxytocin antagonists: Studies on 1-(1-{4- [1-(2-methyl-1-oxidopyridin-3-ylmethyl)piperidin-4-yloxy].2methoxybenzoyl}- 4-yl)-1,4-dihydrobenz[d][1,3]oxazin-2-one (L-372,662) and related pyridines

The previously reported oxytocin antagonist L-371,257 (2) has been modified at its acetylpiperidine terminus to incorporate various pyridine N- oxide groups. This modification has led to the identification of compounds with improved pharmacokinetics and excellent oral bioavailability. The pyridine N-oxide series is exemplified by L-372,662 (30), which possessed good potency in vitro (Ki = 4.1 nM, cloned human oxytocin receptor) and in vivo (intravenous AD50 = 0.71 mg/kg in the rat), excellent oral bioavailability (90% in the rat, 96% in the dog), good aqueous solubility (>8.5 mg/mL at pH 5.2) which should facilitate formulation for iv administration, and excellent selectivity against the human arginine vasopressin receptors. Incorporation of a 5-fluoro substituent on the central benzoyl ring of this class of oxytocin antagonists enhanced in vitro and in vivo potency but was detrimental to the pharmacokinetic profiles of these compounds. Although lipophilic substitution around the pyridine ring of compound 30 gave higher affinity in vitro, such substituents were a metabolic liability and caused shortfalls in vivo. Two approaches to prevent this metabolism, addition of a cyclic constraint and incorporation of trifluoromethyl groups, were examined. The former approach was ineffective because of metabolic hydroxylation on the constrained ring system, whereas the latter showed improvement in plasma pharmacokinetics in some cases.

1--2-methoxybenzoyl>piperidin-4-yl>-4H-3,1-benzoxazin-2(1H)-one (L-371,257): A New, Orally Bioavailable, Non-Peptide Oxytocin Antagonist

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