On November 9, 2000, Dow, Robert Lee; Liu, Kevin Kun-Chin; Morgan, Bradley Paul; Swick, Andrew Gordon published a patent.Reference of 4-(Chloromethyl)-2-methoxy-6-methylpyridine The title of the patent was Preparation of nonracemic octahydrophenanthrene and other tricyclic derivatives as selective modulators of glucocorticoid receptors. And the patent contained the following:
Title compounds [e.g., I; D = CR7, CR7R16, N, NR7, O’ E = C, CR6, N; F = CR4, CR4R5, O; R = XR1; R1 = H, alkyl, acylalkyl, arylalkyl, etc.; R2 = H, halo, alkyl, alkoxy, etc.; R3 = H, alkyl, arylalkyl, etc.; 1 of R2,R3 = null when adjacent dashed line = bond; R4,R5 = H, cyano, alkyl, alkoxy, etc.; R4R5 = O; R6 = H, cyano, alkyl, alkoxy, OH, etc.; R7,R16 = H, halo, cyano, alkyl, etc.; R7R16 = O; R8R9 = atoms to complete a substituted heteroaromatic ring; R14,R15 = H, halo, alkyl, alkoxy, etc.; R14R15 = O when adjacent dashed lines = null; X = bond, CH2, CH(OH), CO; Z = (un)substituted CH2, -CH2CH2, -CH2CO, CO, etc.; dashed lines = optional bonds] were prepared as glucocorticoid receptor modulators (no data). E.g., 6-methoxy-2-tetralone was alkylated by formation of the pyrrolidine enamine and alkylation with benzyl bromide; the benzylated ketone then undergoes asym. Michael addition with Me vinyl ketone in the presence of (S)-(-)-α-methylbenzylamine followed by cyclocondensation with sodium methoxide to give a nonracemic methoxytetrahydrophenanthrenone derivative E.g., demethylation of the methoxytetrahydrophenanthrenone with boron trichloride, reduction of the enone with lithium and ammonia, addition of 1-lithiopropyne to the ketone, formation of the aryl triflate with triflic anhydride and carbonylation with carbon monoxide in the presence in the presence of palladium acetate and bis(diphenylphosphino)propanol gives an hydroxyoctahydrophenanthrenecarboxylic acid derivative which is coupled with 4-(aminomethyl)pyridine in the presence of trimethylaluminum to give the octahydrophenanthrenecarboxamide II as one of the title compounds The experimental process involved the reaction of 4-(Chloromethyl)-2-methoxy-6-methylpyridine(cas: 1227595-34-7).Reference of 4-(Chloromethyl)-2-methoxy-6-methylpyridine
The Article related to nonsteroidal glucocorticoid receptor selective agonist antagonist preparation, treatment obesity diabetes inflammation nonsteroidal glucocorticoid receptor modulator, glucocorticoid receptor modulator preparation and other aspects.Reference of 4-(Chloromethyl)-2-methoxy-6-methylpyridine