1065474-24-9

Upstream product

• 940-11-4 N-methyl-N-nitroso-p-anisidine 
• 55305-43-6 N-cyano-N-phenyl-p-toluenesulfonamide 
• 553-90-2 Dimethyl oxalate 
• 23842-82-2 2-amino-5-methoxybenzonitrile 

Downstream Products

• 1065474-38-5 3-methoxy-6-[methyl(2-methylprop-2-en-1-yl)amino]benzonitrile 

Relevant academic research and scientific papers

Rhodium(III)-Catalyzed Direct Cyanation of Aromatic C-H Bond to Form 2-(Alkylamino)benzonitriles Using N-Nitroso As Directing Group

2-(Alkylamino)benzonitriles were synthesized via a rhodium-catalyzed cyanation on the aryl C-H bond and subsequent denitrosation of N-nitrosoarylamines using a removable nitroso as the directing group, in which N-cyano-N-phenyl-p-methylbenzenesulfonamide (NCTS) was used as the "CN" source. Various substituents on the aryl ring and amino group of N-nitrosoarylamines tolerated the reaction, and the corresponding products were achieved in moderate to good yields.

PYRAZOLOPYRIDINES AND PYRAZOLOPYRIMIDINES

A compound having the structure: or a pharmaceutically acceptable salt thereof, or a pharmaceutically acceptable solvate of said compound or pharmaceutically acceptable salt, wherein A and A′ are independently C or N, where C may be unsubstituted or substituted by halo or C1-C6 alkyl; R and R0 are independently selected from the group consisting of H, C1-C6 alkyl, hydroxy(C1-C6 alkyl), phenyl(C1-C6 alkyl), and —(CH2)n—W, where W is C3-C8 cycloalkyl, phenyl, naphthyl, 5- or 6-membered heteroaryl or heterocyclic containing 1-3 N, S and/or O atoms, —SO2—R′, —NHSO2—R′, —NR″SO2—R′ and SR′, where R′ and R″ are independently C1-C6 alkyl or C3-C8 cycloalkyl, etc.; wherein each of said alkyl, cycloalkyl, heterocyclic, phenyl, naphthyl or heteroaryl may be unsubstituted or substituted by phenyl, heteroaryl, etc.; or, R and R0 and the N atom to which they are bonded together form a monocyclic or bicyclic heterocyclic ring which may be unsubstituted or substituted by (a) halo, hydroxy, heteroaryl, C1-C6 alkyl, C1-C6 alkoxy, etc., or (b) —(CH2)n—W, where W is C3-C8 cycloalkyl, phenyl, etc.; R1 is H, halo or cyano; R2 and R2′ are independently H, C1-C6 alkyl, cyano, C1-C6 alkoxy, C1-C6 alkylthio, or C3-C8 cycloalkyl where alkyl, alkoxy, or cycloalkyl is optionally substituted by one or more fluorine atoms; X is a bond, —CO—, —CONH—, —SO2—, —SONH—, or —(CH2)m—; R3 is H, C1-C4 alkyl, phenyl, naphthyl, 5- or 6-membered heteroaryl or heterocyclic containing 1-3 N atoms, a 5-membered heteroaryl or heterocyclic, etc., or (c) 2 O or S atoms and 0-2 N atoms; wherein each of said phenyl, naphthyl, heteroaryl or heterocyclic is optionally substituted by alkyl, 1 substituent —Y—R4 and/or 1-4 substituents each independently selected from R5; with the proviso that when X is —CO— or —SO2—, R3 is not H; Y is a bond, —(CH2)m— or —O—; R4 is (a) H, C1-C6 alkyl, C3-C8 cycloalkyl, halo, oxo, —OR6, —NR7R8, —SR6, —SOR9, —SO2R9, —COR6, —OCOR6, —OCOR6, —NR6COR6, —CONR7R8, etc.; (b) phenyl or naphthyl, said phenyl and naphthyl being optionally substituted with 1-5 substituents selected from C1-C6 alkyl, C3-C8 cycloalkyl, halo, cyano, —OR6, —NR7R8, etc.; or (c) a 3 to 8-membered saturated or partially unsaturated monocyclic heteroaryl, etc.; R6 is H, C1-C6 alkyl or C3-C8 cycloalkyl, etc.; R7 and R8 are each independently H, C1-C6 alkyl or C3-C8 cycloalkyl or are taken together with the nitrogen atom to which they are attached to form a 4-, 5- or 6-membered saturated heterocyclic ring containing 1-2 nitrogen atoms or 1 nitrogen and 1 oxygen atom, said C1-C6 alkyl is optionally substituted by C3-C8 cycloalkyl, halo, etc., and said heterocyclic ring being optionally substituted by one or more C1-C6 alkyl or C3-C8 cycloalkyl groups; R9 is C1-C6 alkyl or C3-C8 cycloalkyl; and, m and n are independently 0, 1, 2 or 3. The invention also relates to pharmaceutically acceptable salts of these compounds and to pharmaceutically acceptable solvates thereof; to compositions containing such compounds; and to the uses of such compounds in the treatment of various diseases, particularly asthma and COPD.