51270-35-0

Upstream product

• 75-64-9 tert-butylamine 
• 1939-99-7 benzenesulfonyl chloride 
• 675622-48-7 O-benzylsulfonyl-N-[phenyl(1-phenylethyl)phosphinoyl]hydroxylamine 
• 57267-76-2 sodium α-toluenesulfonate 
• 329-98-6 phenylmethylsulphonyl fluoride 

Downstream Products

• 4563-33-1 phenyl-methanesulfonic acid amide 
• 1445902-99-7 N-(4-bromobenzyl)-N-tert-butyl-1-phenylmethanesulfonamide 
• 1445901-63-2 N-(4-(4-acetylpiperazin-1-yl)benzyl)-N-tert-butyl-1-phenylmethanesulfonamide 
• 56221-20-6 1,3,5-tris(benzylsulphonyl)hexahydro-1,3,5-triazine 
• 110654-64-3 C-Phenyl-N-(2,2,2-trichloro-1-phenylmethanesulfonylamino-ethyl)-methanesulfonamide 
• 110654-63-2 4-(4-Nitro-phenyl)-3,4-dihydro-1H-benzo[d][1,2]thiazine 2,2-dioxide 
• 110654-44-9 3-Benzyl-3,4-dihydro-1H-benzo[d][1,2]thiazine 2,2-dioxide 
• 58908-07-9 N-Benzyliden-toluol-ω-sulfonsaeureamid 
• 89557-12-0 2-Hydroxy-1-phenyl-ethanesulfonic acid tert-butylamide 
• 120360-29-4 2-tert-Butyl-1,1-dioxo-5,6-diphenyl-1,4-dihydro-2H-1λ⁶-[1,2,4]thiadiazin-3-one 
• 22457-16-5 N-tert.-Butyl-phenyl-nitromethansulfonamid 
• 51270-44-1 C,C-Dibromo-N-tert-butyl-C-phenyl-methanesulfonamide 
• 51270-42-9 C-Bromo-N-tert-butyl-C-phenyl-methanesulfonamide 

Relevant academic research and scientific papers

A Broad-Spectrum Catalytic Amidation of Sulfonyl Fluorides and Fluorosulfates**

A broad-spectrum, catalytic method has been developed for the synthesis of sulfonamides and sulfamates. With the activation by the combination of a catalytic amount of 1-hydroxybenzotriazole (HOBt) and silicon additives, amidations of sulfonyl fluorides and fluorosulfates proceeded smoothly and excellent yields were generally obtained (87–99 %). Noticeably, this protocol is particularly efficient for sterically hindered substrates. Catalyst loading is generally low and only 0.02 mol % of catalyst is required for the multidecagram-scale synthesis of an amantadine derivative. In addition, the potential of this method in medicinal chemistry has been demonstrated by the synthesis of the marketed drug Fedratinib via a key intermediate sulfonyl fluoride 13. Since a large number of amines are commercially available, this route provides a facile entry to access Fedratinib analogues for biological screening.

BENZYL SULFONAMIDE DERIVATIVES AS RORc MODULATORS

Compounds of the formula (I) or pharmaceutically acceptable salts thereof, wherein m, n, A, X1, X2, X3, X4, R1, R2, R3a, R3b, R4a and R4b are as defined herein. Also disclosed are methods of making the compounds and using the compounds for treatment of inflammatory diseases such as arthritis.

NEW PYRIDINE ANALOGUES

The present invention relates to certain new pyridin analogues of Formula (I) Chemical formula should be inserted here. Please see paper copy Formula (I) to processes for preparing such compounds, to their utility as P2Y12 inhibitors and as anti-trombotic agents etc, their use as medicaments in cardiovascular diseases as well as pharmaceutical compositions containing them.

Competing sulfonylation and phosphonylation following rearrangement of an O-sulfonyl-N-phosphinoylhydroxylamine with tert-butylamine: Demonstration of a phosphonamidic-sulfonic anhydride intermediate and 18O-labelling evidence on how it may be formed

Reaction of R(Ph)P(O)NHOSO2Bn (R = PhMeCH) with Bu tNH2 in CH2Cl2 gives a mixture of RP(O)(NHPh)NHBut and ButNHSO2Bn, the proportion of the sulfonamide increasing steadily (14.6% to 32.9%) as the concentration of amine is reduced (8.0 to 0.2 mol dm-3). Apparently the phenyl and sulfonate groups in the substrate become transposed, giving a phosphonamidic-sulfonic anhydride RP(O)(NHPh)OSO2Bn which then reacts at the phosphorus or sulfur atom to give the final products; an authentic sample of the anhydride gives similar mixtures of products. Substrate labelled with 18O in the sulfonyl position (57 mol% one 18O atom) gives sulfonamide containing most but not all of the label (43.7 mol% one 18O atom with 2.0 mol dm-3 amine). This implies partial equilibration of the three sulfonate oxygen atoms during rearrangement, or after the anhydride intermediate has been formed.

α,N-Alkanesulfonamide Dianions: Formation and Chemoselective C-Alkylation

Mono-N-substituted alkanesulfonamides such as 11 (Scheme I) can be treated with 2 equiv of a strong base (n-butyllithium or LDA) to generate the hitherto unreported dianionic species 12.Addition of electrophiles (alkylhalides, aldehydes, ketones, nitriles) to THF solutions of these dianions results in clean, chemoselective reaction on the carbon atom.Removal of the "protecting" group from nitrogen releases a primary sulfonamide, which may then be selectively functionalized.This method permits the preparation of a wide variety of substituted sulfonamides that might otherwise prove difficult to synthesize.As demonstration of the further utility of these adducts, β-hydroxy sulfonamides such as 14 were converted to either β-styrenesulfonamides 15 (and 16) or 1,2-thiazetidine 1,1-dioxides (18) (Scheme II).