A new synthesis of 1,2,4-triazolin-5-ones:: application to the convergent synthesis of an NK1 antagonist

被引：36

作者：

Cowden, CJ ^{[1
]}

Wilson, RD ^{[1
]}

Bishop, BC ^{[1
]}

Cottrell, IF ^{[1
]}

Davies, AJ ^{[1
]}

Dolling, UH ^{[1
]}

机构：

[1] Merck Sharp & Dohme Res Labs, Dept Proc Res, Hoddesdon EN11 9BU, Herts, England

来源：

TETRAHEDRON LETTERS | 2000年 / 41卷 / 44期

关键词：

D O I：

10.1016/S0040-4039(00)01548-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Chlorotriazolinone 4 has been synthesised in a single step via the novel condensation of semicarbazide hydrochloride with orthoester 8. Alkylation of secondary amine 3 with compound 4 proceeds in 99% yield to afford the target NK, antagonist 1. (C) 2000 Published by Elsevier Science Ltd.

引用

页码：8661 / 8664

页数：4

共 12 条

[1] THERMAL-BEHAVIOR OF 3-PHENYL-1,2,4-OXADIAZOL-5-YLHYDRAZINES [J].

ADEMBRI, G ;

CAMPARINI, A ;

PONTICELLI, F ;

TEDESCHI, P .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1981, (06) :1703-1706

[2] Structural optimization affording 2-(R)-(1-(R)-3,5-bis(trifluoromethyl)phenylethoxy)-3-(S)-(4-fluoro)phenyl-4-(3-oxo-1,2,4-triazol-5-yl)methylmorpholine, a potent, orally active, long-acting morpholine acetal human NK-1 receptor antagonist [J].

Hale, JJ ;

Mills, SG ;

MacCoss, M ;

Finke, PE ;

Cascieri, MA ;

Sadowski, S ;

Ber, E ;

Chicchi, GG ;

Kurtz, M ;

Metzger, J ;

Eiermann, G ;

Tsou, NN ;

Tattersall, FD ;

Rupniak, NMJ ;

Williams, AR ;

Rycroft, W ;

Hargreaves, R ;

MacIntyre, DE .

JOURNAL OF MEDICINAL CHEMISTRY, 1998, 41 (23) :4607-4614

[3] Synthesis of optically active 2-chloromethyl-2-oxazolines by the ortho-ester condensation method using triethyl orthochloroacetate [J].

Kamata, K ;

Sato, H ;

Takagi, E ;

Agata, I ;

Meyers, AI .

HETEROCYCLES, 1999, 51 (02) :373-378

[4] The preparation of orthoesters [J].

McElvain, SM ;

Nelson, JW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1942, 64 :1825-1827

[5] REACTIONS ON SULFUR MONOCHLORIDE WITH SOME AROMATIC ALDEHYDE SEMICARBAZONES AND THIOSEMICARBAZONES - NEW SYNTHESES OF SUBSTITUTED 2,4-DIHYDRO-1,2,4-TRIAZOL-3-ONES, 2,4-DIHYDRO-1,2,4-TRIAZOLE-3-THIONES AND 2-AMINO-1,3,4-OXADIAZOLES [J].

MILCENT, R ;

NGUYEN, TH .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1986, 23 (03) :881-883

[6] CODEINE ANALOGS - SYNTHESIS OF SPIRO[BENZOFURAN-3(2H),4'-PIPERIDINES] AND OCTAHYDRO-1H-BENZOFURO[3,2-E]ISOQUINOLINES [J].

MOOS, WH ;

GLESS, RD ;

RAPOPORT, H .

JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (25) :5064-5074

[7] 2-CHLORO-1,1,1-TRIETHOXYETHANE AND ITS USE IN A VERSATILE SYNTHESIS OF SUBSTITUTED, 2-CHLOROMETHYL HETEROCYCLES INCLUDING BENZOTHIAZOLE AND BENZOXAZOLE [J].

MYLARI, BL ;

SCOTT, PJ ;

ZEMBROWSKI, WJ .

SYNTHETIC COMMUNICATIONS, 1989, 19 (16) :2921-2924

[8]

REGOLI D, 1994, PHARMACOL REV, V46, P551

[9] DISILYLATED COMPOUNDS AS PRECURSORS OF HETEROCYCLES - SYNTHESIS OF BENZIMIDAZOLES, TRIAZOLES, FURAN AND PYRROLE [J].

RIGO, B ;

VALLIGNY, D ;

TAISNE, S ;

COUTURIER, D .

SYNTHETIC COMMUNICATIONS, 1988, 18 (02) :167-180

[10] AMBIDENT OXIDATIVE RING-CLOSURE OF SEMICARBAZONES [J].

SCOTT, FL ;

BUTLER, RN ;

LAMBE, TM .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1972, (15) :1918-&

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