2909-82-2

Usage

InChI:InChI=1/C11H17N/c1-8-7-9(11(2,3)4)5-6-10(8)12/h5-7H,12H2,1-4H3

Upstream product

• 78-83-1 2-methyl-propan-1-ol 
• 636-21-5 o-toluidine hydrochloride 
• 95-53-4 o-toluidine 
• 115-11-7 isobutene 
• 769-92-6 4-tert-Butylaniline 
• 823-96-1 Trimethylboroxine 
• 103273-01-4 2-bromo-4-tert-butylaniline 
• 1075-38-3 m-t-butyltoluene 
• 13061-96-6 dihydroxy-methyl-borane 

Downstream Products

• 1397706-31-8 C₁₉H₂₀N₄ 
• 409097-55-8 2-Bromo-N-(4-tert-butyl-2-methylphenyl)acetamide 
• 683223-25-8 4-(tert-butyl)-2-methylphenylisothiocyanate 
• 33691-85-9 4-(tert-butyl)-2-methylbenzoic acid 
• 71005-10-2 4-(tert-butyl)-2-methylbenzonitrile 
• 337471-08-6 acetic acid-(4-tert-butyl-2-methyl-anilide) 

Relevant academic research and scientific papers

COMPOUNDS, COMPOSITIONS, AND METHODS FOR MODULATING CFTR

The present disclosure is directed to disclosed compounds that modulate, e.g., address underlying defects in cellular processing of CFTR activity.

Electrochemical Amination of Less-Activated Alkylated Arenes Using Boron-Doped Diamond Anodes

The anodic C-H amination of aromatic compounds is a powerful and versatile method for the synthesis of aniline derivatives. By using boron-doped diamond (BDD) anodes, a method initially described by Yoshida et al. for electron-rich arenes was expanded to less-activated aromatic systems e.g., simple alkylated benzene derivatives. Anodes based on sp3 carbon seem to be the key for the electrochemical amination reaction. The corresponding primary anilines are obtained in good yields. Despite the cationic intermediates of the electrolytic reaction tert-butyl moieties are tolerated.

Oxidative fluorination of N-arylsulfonamides

We report a late stage oxidative nucleophilic fluorination of N-arylsulfonamides, a class of compounds so far not considered as precursors to 4-fluorophenyl sulfonamides. By installing a para-positioned tert-butyl substituent on the aniline, oxidative fluorination takes place regioselectively in the presence of HF·pyridine and PIDA. This methodology has been shown to give good yields for a variety of ortho- and meta-functionalised N-arylsulfonamides and has been adapted for radiofluorination to give 4-[18F]fluorophenyl sulfonamides under carrier added conditions.

Syntheses and15N NMR Spectra of Iminodiaziridines - Ring-Expansions of 1-Aryl-3-iminodiaziridines to 1H- and 3aH-Benzimidazoles, 2H-Indazoles, and 5H-Dibenzo[d,f] [1,3]diazepines

Iminodiaziridines are synthesized, by (i) 1,3-dehydrochlorination with potassium, teri-butoxide of N-chloroguanidines, generated in situ from. N,N′,N″-substituted guanidines with tert-butyl hypochlorite, and (ii) base-mediated 1,3-elimination of sulfuric acid from N,N',N″- substituted hydroxyguanidine O-sulfonic acids. At elevated temperatures, (alkylimino)diaziridines undergo valence isomerization by 1,3shift, [2+1] cycloelimination to afford isocyanides and diazenes, and ring-opening elimination to yield alkylideneguanidines. N′-Aryl-N-hydroxyguanidine O-sulfonic acids furnish (N-arylimino)diaziridines, but no 1-aryl-3- iminodiaziridines, instead giving rearranged isomere. Precursors containing perdeuterated feri-butyl groups give rearranged products that show complete scrambling. This indicates that l-aryl-3iminodiaziridines are intermediates that undergo very rapid I degenerate valence isomerization. Provided that the ortho aryl positions are substituted, high yields of (arylimino)diaziridines are obtained, along with 2-imino-2,3-dihydro-3aHbenzimidazoles, Otherwise, 2-amino-lH-benzimidazoles and strongly fluorescent 3-amino-2H-indazoles, originating from rearrangements of the elusive l-aryl-3-iminodiaziridines, predominate. N',N″-Diaryl-N-hydroxyguanidine O-sulfonic acids give only rearranged products: a 2-amino-1H-benzimidazole and a 6-amino-5H-dibenzo[d,f][1. 3]diazepine if aryl = phenyl, or a 2-imino-2,3-dihydro-3aH-benzimidazole if aryl = mesityl. 3aH-Benzimidazoles slowly dimerize through Diels-Alder reactions. 15N NMR signals were assigned, to the syn and anti ring nitrogen atoms of iminodiaziridines with the help of a combination of homonuclear NOE and HNHMBC or HN-gHMBC experiments.