64109-38-2Relevant academic research and scientific papers
Improved synthesis of sterically encumbered heteroaromatic biaryls from aromatic β-keto esters
Rosen, Brandon R.,Ul Sharif, Ehesan,Miles, Dillon H.,Chan, Nicholas S.,Leleti, Manmohan R.,Powers, Jay P.
supporting information, (2020/03/25)
A protocol for the synthesis of hindered 4-aryl 2-aminopyrimidines from β–keto esters is described. The process employs trifluoroethanol as an essential additive to promote the guanidine condensation reaction, enabling the synthesis of 25 aryl- and heteroaryl substituted aminopyrimidines in good yields and high purities with no column chromatography. The conditions described herein are readily scalable and have been employed in the large-scale synthesis of the clinical A2a/A2bR antagonist AB928.
Preparation method of N,N-dimethyl benzoate composite
-
Paragraph 0026, (2016/10/09)
The invention relates to a preparation method of an N,N-dimethyl benzoate composite, in particular to a preparation method for preparing N,N-dimethyl benzoate by using N,N-dimethylaniline, bi(trichloromethyl)carbonic ester and alcohol as raw materials. The raw materials are cheap and easy to obtain, the yield is high, a midbody does not need to be purified, a continuous reaction can be performed without replacing solvents, the preparation method is cheap, environmentally friendly, easy to implement and suitable for industrialization, and the method can be used for preparing the important chemical and medical midbody through N,N-dimethyl benzoyl chloride.
Synthesis and cytotoxicity of 6-pyrrolidinyl-2-(2-substituted phenyl)-4-quinazolinones
Hour, Mann-Jen,Yang, Jai-Sing,Lien, Jin-Cherng,Kuo, Sheng-Chu,Huang, Li-Jiau
, p. 785 - 790 (2008/03/12)
In our continuing search for potential anticancer candidates, 2-(3-methoxyphenyl)-6-pyrrolidinyl-4-quinazolinone (JJC-1) was selected as the lead compound. Starting 5-pyrrolidinyl-2-aminobenzamide was prepared using standard methodology from 5-chloro-2-ni
Contra-Friedel-Crafts tert-butylation of substituted aromatic rings via directed metallation and sulfinylation
Clayden, Jonathan,Stimson, Christopher C.,Keenan, Martine
, p. 1393 - 1394 (2008/02/03)
Directed metallation and sulfinylation yields sulfoxides which undergo ipso nucleophilic aromatic substitution with tertiary and secondary alkyllithiums, giving aromatic rings bearing alkyl groups generally incompatible with directed metallation methods and with regioselectivity complementary with classical Friedel-Crafts substitution. The Royal Society of Chemistry 2006.
Benzoxazole carboxamides for treating CINV and IBS-D
-
Page/Page column 23-24, (2008/06/13)
Compounds of formulae I and II: are disclosed as 5-HT3 inhibitors. Those compounds that exhibit central activity are useful in treating CINV; those that inhibit peripheral receptors are useful to treat IBS-D.
SYNTHESIS OF 1-ACYL- AND 1-(THIOACYL)-4-BENZYLPIPERAZINES AS POTENTIAL ANTIDEPRESSANTS
Kmonicek, Vojtech,Svatek, Emil,Holubek, Jiri,Ryska, Miroslav,Valchar, Martin,Protiva, Miroslav
, p. 1817 - 1827 (2007/10/02)
2-Nitro, 3-nitro- and 4-nitrobenzoyl chloride were reacted with 1-benzylpiperazine in benzene in the presence of triethylamine and gave the amides IV-VI, the first of which is considered a bioisostere of the antidepressant agent piberaline (I). 2-Dimethylamino-, 3-dimethylamino- and 4-dimethylaminobenzoic acid were treated with thionyl chloride in benzene in the presence of triethylamine or pyridine, and the acid chlorides formed were reacted in situ with 1-benzylpiperazine affording the amides VII-IX.The amides I and IV - VI were transformed by treatment with phosphorus pentasulfide in pyridine to the thioamides X - XIII. 4-(Dimethylaminomethyl)benzoic acid was reacted with 1-benzylpiperazine in dimethylformamide in the presence of N,N'carbonyldiimidazole and afforded the amide XIV.Heating of ethyl 5-methylimidazole-4-carboxylate with 1-benzylpiperazine to 200 - 210 deg C gave the amide XV together with the unexpected 1-benzyl-4-ethylpiperazine (XVI).The oily or crystalline bases of the amino amides or thioamides were mostly transformed to crystalline salts and characterized by spectra.Out of the compounds prepared only X (VUFB-17070) and XIV (VUFB-17114) showed indications of efficacy in tests which are considered indicative of antidepressant activity.Compounds VII, VIII, and X appeared to be mildly antidopaminergic-similarly like piberaline (I), and compounds IV, V, XI, XIV, and XV on the contrary showed signs of dopaminominetic activity.
