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1. (WO2000029411) AN IMPROVED PROCESS FOR THE PREPARATION OF 7-AZAINDOLYL-3-CARBOXYLIC ACID
Latest bibliographic data on file with the International Bureau   

Pub. No.:    WO/2000/029411    International Application No.:    PCT/IB1999/001834
Publication Date: 25.05.2000 International Filing Date: 12.11.1999
Chapter 2 Demand Filed:    13.04.2000    
IPC:
C07D 207/34 (2006.01), C07D 471/04 (2006.01)
Applicants: DOMPE' SPA [IT/IT]; Via Campo di Pile, I-67100 L'Aquila (IT) (For All Designated States Except US).
CESTA, Maria, Candida [IT/IT]; (IT) (For US Only).
CURTI, Roberto [IT/IT]; (IT) (For US Only).
NICOLINI, Luca [IT/IT]; (IT) (For US Only).
MANTOVANINI, Marco [IT/IT]; (IT) (For US Only)
Inventors: CESTA, Maria, Candida; (IT).
CURTI, Roberto; (IT).
NICOLINI, Luca; (IT).
MANTOVANINI, Marco; (IT)
Agent: BENEDUCE, Gianna; Via Poggibonsi, 7, I-20146 Milan (IT)
Priority Data:
MI98A002480 17.11.1998 IT
Title (EN) AN IMPROVED PROCESS FOR THE PREPARATION OF 7-AZAINDOLYL-3-CARBOXYLIC ACID
(FR) PROCEDE AMELIORE DE PREPARATION D'ACIDE 7-AZAINDOLYL-3-CARBOXYLIQUE
Abstract: front page image
(EN)A process for the preparation of 7-azaindolyl-3-carboxylic acid is described starting from succinonitrile (VIII) which is condensed with ethyl formate and the so formed salt of 2-hydroxymethylenebutyrronitrile (VII) is reacted with tert.butylamine to give N-tert.butylaminomethylene-succinonitrile (VI) which is reacted in a warm ambience in the presence of a base to give 1-tert.butyl-2-amino-4-cyanopyrrole (V) which is reacted with a malondialdehyde acetal to give 1-tert.butyl-3-cyano-7-azaindole (IV) which in a suitable solvent is heated under reflux with a Lewis acid and the corresponding dichloroderivative (III), treated with a suitable proton donor, gives 3-cyano-7-azaindole (II) which is hydrolyzed at the temperature of 70 °C at pH 2.5 to provide 7-azaindolyl-3-carboxylic acid (I).
(FR)L'invention concerne un procédé de préparation d'acide 7-azaindolyl-3-carboxylique à partir de succinonitrile (VIII) lequel est condensé avec du formate d'éthyle et consistant à faire réagir le sel ainsi formé de 2-hydroxyméthylènebutyrronitrile (VII) avec une tert.butylamine afin de donner du N-tert.butylaminométhylènesuccinonitrile (VI), que l'on fait réagir dans une ambiance tiède en présence d'une base pour donner une 1-tert.butyl-2-amino-4-cyanopyrrole (V), que l'on fait réagir avec un acétal de malondialdéhyde pour donner une 1-tert.butyl-3-cyano-7-azainode (IV), laquelle dans un solvant adapté est chauffée sous reflux avec un acide de Lewis et le dérivé dichloro (III) correspondant, traité avec un donneur de protons approprié, et donne une 3-cyano-7-azaindole (II) laquelle est hydrolysée à la température de 70 °C au pH de 2,5 pour produire l'acide 7-azaindolyl-3-carboxylique (I).
Designated States: AE, AL, AM, AT, AU, AZ, BA, BB, BG, BR, BY, CA, CH, CN, CR, CU, CZ, DE, DK, DM, EE, ES, FI, GB, GD, GE, GH, GM, HR, HU, ID, IL, IN, IS, JP, KE, KG, KP, KR, KZ, LC, LK, LR, LS, LT, LU, LV, MA, MD, MG, MK, MN, MW, MX, NO, NZ, PL, PT, RO, RU, SD, SE, SG, SI, SK, SL, TJ, TM, TR, TT, TZ, UA, UG, US, UZ, VN, YU, ZA, ZW.
African Regional Intellectual Property Organization (GH, GM, KE, LS, MW, SD, SL, SZ, TZ, UG, ZW)
Eurasian Patent Organization (AM, AZ, BY, KG, KZ, MD, RU, TJ, TM)
European Patent Office (AT, BE, CH, CY, DE, DK, ES, FI, FR, GB, GR, IE, IT, LU, MC, NL, PT, SE)
African Intellectual Property Organization (BF, BJ, CF, CG, CI, CM, GA, GN, GW, ML, MR, NE, SN, TD, TG).
Publication Language: English (EN)
Filing Language: English (EN)