On September 30, 2004, Goble, Stephen D.; Pasternak, Alexander; Mills, Sander G.; Zhou, Changyou; Yang, Lihu published a patent.Quality Control of (6-(Trifluoromethyl)pyridin-3-yl)methanol The title of the patent was Preparation of (tetrahydropyranylamino)cyclopentanecarbonyl-substituted fused azaheterocycles as modulators of cytokine receptors such as CCR2. And the patent contained the following:
Compounds I [A = R82C, C(:O), NR8, O; B = R22C, O, S(:O), SO2, NSO2R14, NC(:O)R13, NC(:O)NR122,C(:O); D, X = C, N; E = (CH2)n; G = CH:CH, CH2CH2; Y = O, R12N, S, S(:O), SO2, R112C, etc.; n = 0-2; R1 = H, NC, (un)substituted alkyl, heterocyclyl, Ph, R122N, R13C(:O)N(R12), R14SO2N(R12), R11C(:O), R122NC(:O); R2 = H, alkyl, F, HO, heterocyclyl, R13C(:O)NH, etc.; R3, R4 = absent, H, (un)substituted alkyl, HO, Cl, O, etc.; R5 = (un)substituted alkyl, alkoxy, alkylcarbonyl, alkylthio, pyridyl, etc.; R8 = H, alkyl, (un)substituted alkylcarbonylalkyl; R11 = HO, H, (un)substituted alkyl, alkoxy, cycloalkyl, benzyl, phenyl; R12 = H, (un)substituted alkyl, benzyl, Ph, cycloalkyl; R13 = H, (un)substituted alkyl, alkoxy, benzyl, Ph, cycloalkyl; R14 = H, HO, (un)substituted alkyl, benzyl, Ph, cycloalkyl; R15 = H, (un)substituted alkyl; R16 = H, (un)substituted alkyl, alkoxy, cycloalkyl, F, HO, etc.; R17 = H, HO, (un)substituted alkyl, alkoxy, R11C(:O); R18 = H, F, (un)substituted alkyl, cycloalkoxy, alkoxy; R16 and either R17 or R18 may be joined in a ring] such as II are prepared as modulators of cytokine receptors such as CCR2 for the treatment of inflammatory and immune system disorders such as rheumatoid arthritis. Coupling of (tert-butoxy)(trifluoromethyl)benzylamine III and nonracemic (tetrahydropyranylamino)cyclopentanecarboxylic acid IV followed by cleavage of the tert-Bu group, cyclocondensation with paraformaldehyde, and cleavage of the trifluoroacetamide yields II as its hydrochloride salt. III is prepared by nucleophilic substitution of 2-fluoro-5-(trifluoromethyl)benzonitrile with potassium tert-butoxide followed by hydrogenation of the nitrile moiety. IV is prepared by Boc protection of the amine moiety of V, benzylation of the carboxylic acid group, cleavage of the Boc group, reductive amination of the amine with tetrahydropyran-4-one, trifluoroacetylation of the secondary amine, stereoselective alkylation of the ester with potassium bis(trimethylsilyl)amide and iso-Pr iodide, and hydrogenolysis of the benzyl ester; a second route to IV is also described. Compounds of the invention inhibit CCR2 with IC50 values of < 1 μM (no data). The experimental process involved the reaction of (6-(Trifluoromethyl)pyridin-3-yl)methanol(cas: 386704-04-7).Quality Control of (6-(Trifluoromethyl)pyridin-3-yl)methanol
The Article related to tetrahydropyranylamino cyclopentanecarbonyl substituted fused azaheterocycle preparation cytokine receptor modulator, ccr2 modulator tetrahydropyranylamino cyclopentanecarbonyl substituted fused azaheterocycle preparation and other aspects.Quality Control of (6-(Trifluoromethyl)pyridin-3-yl)methanol
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