725228-49-9

Basic information

• Product Name: tert-butyl 3-(piperidin-4-yl)benzylcarbaMate
• Synonyms: tert-butyl 3-(piperidin-4-yl)benzylcarbaMate
• CAS NO: 725228-49-9
• Molecular Formula: C₁₇H₂₆N₂O₂
• Molecular Weight: 290.40054
• Mol File: 725228-49-9.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 440.7±45.0 °C(Predicted)
• Appearance: /
• Density: 1.045±0.06 g/cm3(Predicted)
• PKA: 12.23±0.46(Predicted)
• CAS DataBase Reference: tert-butyl 3-(piperidin-4-yl)benzylcarbaMate(CAS DataBase Reference)
• NIST Chemistry Reference: tert-butyl 3-(piperidin-4-yl)benzylcarbaMate(725228-49-9)
• EPA Substance Registry System: tert-butyl 3-(piperidin-4-yl)benzylcarbaMate(725228-49-9)

Safety Data

• Hazardous Substances Data: 725228-49-9(Hazardous Substances Data)

Upstream product

• 150255-96-2 (3‐cyanophenyl)boronic acid 
• 6952-59-6 3-cyanobromobenzene 
• 19099-93-5 benzyl 4-oxo-1-piperidinecarboxylate 
• 286961-24-8 benzyl 1,2,3,6-tetrahydro-4-(trifluoromethylsulphonyloxy)-pyridine-1-carboxylate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 375854-77-6 2-(trimethylsilyl)ethyl 1,2,3,6-tetrahydro-4-trifluoromethylsulfonyloxy-pyridine-1-carboxylate 
• 181701-30-4 4-oxo-piperidine-1-carboxylic acid 2-(trimethylsilyl)ethyl ester 
• 375854-52-7 2-(trimethylsilanyl)ethyl 4-(3-cyanophenyl)-3,6-dihydro-2H-pyridine-1-carboxylate 
• 864069-18-1 4-[3-(tert-butoxycarbonylaminomethyl)phenyl]piperidine p-toluenesulfonic acid salt 
• 864069-14-7 4-[3-(tert-butoxycarbonylaminomethyl)phenyl]piperidine acetic acid salt 

Downstream Products

• 725228-58-0 5-(2-fluoro-phenylethynyl)-furan-2-carboxylic acid ethyl ester 
• 725228-52-4 (3-{1-[5-(2-fluorophenylethynyl)-furan-2-carbonyl]-piperidin-4-yl}-benzyl)-carbamic acid tert-butyl ester 
• 864069-20-5 4-[3-(tert-butoxycarbonylaminomethyl)phenyl]-1-[5-bromo-2-furanoyl]piperidine 
• 1290056-81-3 (E)-tert-butyl 3-(1-(3-(3,4-dihydroxyphenyl)acryloyl)piperidin-4-yl)benzylcarbamate 
• 1290056-93-7 Tert-butyl 3-(1-(3-hydroxybenzoyl)piperidin-4-yl)benzylcarbamate 
• 1290056-94-8 ethyl 2-(3-(4-(3-(((tert-butoxycarbonyl)amino)methyl)phenyl)piperidine-1-carbonyl)phenoxy)acetate 
• 1290056-95-9 2-(3-(4-(3-(((tert-butoxycarbonyl)amino)methyl)phenyl)piperidine-1-carbonyl)phenoxy)acetic acid 
• 1290056-96-0 tert-butyl 3-(1-(3-(2-(2,2-dimethyldihydro-3aH-[1,3]dioxolo[4,5-c]pyrrol-5(4H)-yl)-2-oxoethoxy)benzoyl)piperidin-4-yl)benzylcarbamate 
• 1290053-89-2 (4-(3-(aminomethyl)phenyl)piperidin-1-yl)(6,7-dihydroxynaphthalen-1-yl)methanone hydrochloride 
• 1290053-76-7 (4-(3-(aminomethyl)phenyl)piperidin-1-yl)(3-(2,3-dihydroxypropoxy)phenyl)methanone hydrochloride 
• 1290054-55-5 tert-butyl 3-(1-(3,4-dihydroxybenzoyl)piperidin-4-yl)benzylcarbamate 
• 1290053-88-1 (4-(3-(aminomethyl)phenyl)piperidin-1-yl)(6,7-dimethoxynaphthalen-1yl)methanone hydrochloride 
• 1290056-84-6 tert-butyl 3-((1-6,7-dimethoxy-1-napthoyl)piperidin-4-yl)benzyl carbamate 
• 1290053-80-3 [5-({4-[3-(aminomethyl)phenyl]piperidin-1-yl}carbonyl)naphthalen-2-yl]boronic acid hydrochloride 

Relevant articles and documents

Novel, Self-Assembling Dimeric Inhibitors of Human β Tryptase

β-Tryptase, a homotetrameric serine protease, has four identical active sites facing a central pore, presenting an optimized setting for the rational design of bivalent inhibitors that bridge two adjacent sites. Using diol, hydroxymethyl phenols or benzoyl methyl hydroxamates, and boronic acid chemistries to reversibly join two [3-(1-acylpiperidin-4-yl)phenyl]methanamine core ligands, we have successfully produced a series of self-assembling heterodimeric inhibitors. These heterodimeric tryptase inhibitors demonstrate superior activity compared to monomeric modes of inhibition. X-ray crystallography validated the dimeric mechanism of inhibition, and compounds demonstrated high selectivity against related proteases, good target engagement, and tryptase inhibition in HMC1 xenograft models. Screening 3872 possible combinations from 44 boronic acid and 88 diol derivatives revealed several combinations that produced nanomolar inhibition, and seven unique pairs produced greater than 100-fold improvement in potency over monomeric inhibition. These heterodimeric tryptase inhibitors demonstrate the power of target-driven combinatorial chemistry to deliver bivalent drugs in a small molecule form.

INDOLYL-PIPERIDINYL BENZYLAMINES AS BETA-TRYPTASE INHIBITORS

The present invention discloses and claims a series of substituted indolyl-piperidinyl benzylamines of formula (I), wherein R1, R2 and R3 are as described herein. More specifically, the compounds of this invention are inhibitors of β-tryptase and are, therefore, useful as pharmaceutical agents. Additionally, this invention also discloses methods of preparation of substituted indolyl-piperidinyl benzylamines. In one of the embodiments, there is provided the compounds of formula (I) wherein R3 is (II).

Process for the preparation of tryptase inhibitors

This invention is directed to processes for the preparation of compounds of the formula I and their salts, which are useful as tryptase inhibitors, to intermediates useful in the preparation of such compounds, to processes for the preparation of such inte