On January 25, 2007, Uchida, Hideharu; Kosuga, Naoto; Satoh, Tsutomu; Hotta, Daido; Kamino, Tomoyuki; Maeda, Yoshitaka; Amano, Ken-Ichi; Akada, Yasushige published a patent.Quality Control of tert-Butyl (4-(trifluoromethyl)phenyl)carbamate The title of the patent was Preparation of novel 2-(bicyclic heterocyclidene)acetamide derivatives as antagonists of transient receptor potential type 1 (TRPV1). And the patent contained the following:
The title compounds (I) or salts thereof, and solvates of any of them [m, n, p = an integer of 0-2; q = 0, 1; R1 = halo, each (un)substituted hydrocarbyl, heterocyclyl, C1-6 alkoxy, C1-6 alkoxycarbonyl, NH2, HO, CO2H, CONH2, or SO2NH2, C1-6 alkanoyl, C1-6 alkylthio, C1-6 alkylsulfinyl, C1-6 alkylsulfonyl, cyano, NO2; R2 = halo, (un)substituted NH2, hydrocarbyl, or aromatic heterocyclyl, oxo; or two geminal or vicinal R2s together form C2-6 alkylene; R2 and the carbon atom attached to R2 together form a cyclic ring; X1 = O, (un)substituted NH, S, SO, SO2; X2 = CH2, O, (un)substituted NH, S, SO, SO2; Q1 = each (un)substituted heteroaryl, heteroarylalkyl, aryl, or aralkyl; the Cy ring = 5- or 6-membered aryl or heteroaryl; a dotted line represents the condensation of two rings; a wavy line represent E or Z configuration; some exceptions are defined] are prepared These compounds are useful for the treatment or prevention of pains. Thus, tri-Et phosphonoacetate was treated with NaH in THF at ≤20° for 1 h and condensed with 4-chromanone at room temperature overnight to give (E)-(chroman-4-ylidene)acetic acid Et ester which was refluxed in aqueous THF solution containing LiOH and neutralized with 1 N aqueous HCl solution to give (E)-(chroman-4-ylidene)acetic acid (II). II was condensed with 1,4-benzodioxan-6-amine using 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride in CH2Cl2 at room temperature overnight to give (E)-2-(chroman-4-ylidene)-N-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)acetamide (III). III and (E)-2-(8-trifluoromethyl-3,4-dihydrobenzo[b]oxepin-5(2H)-ylidene)-N-(quinoxalin-6-yl)acetamide in vitro showed A2 of ≥100 nM and <100 nM, resp., for antagonizing the capsaicin-induced cellular influx of Ca in CHO cell expressing human TRPV1. Pharmaceutical formulations, e.g. a tablet containing (E)-2-(7-tert-Butylchroman-4-ylidene)-N-(5,6,7,8-tetrahydroquinolin-7-yl)acetamide, were prepared The experimental process involved the reaction of tert-Butyl (4-(trifluoromethyl)phenyl)carbamate(cas: 141940-37-6).Quality Control of tert-Butyl (4-(trifluoromethyl)phenyl)carbamate
The Article related to capsaicin receptor trpv1 antagonist bicyclic heterocyclideneacetamide preparation, bicyclic heterocyclideneacetamide preparation antagonist transient receptor potential type 1, chromanylideneacetamide benzooxepinylideneacetamide preparation treatment prevention pain, pain treatment prevention bicyclic heterocyclideneacetamide preparation and other aspects.Quality Control of tert-Butyl (4-(trifluoromethyl)phenyl)carbamate
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