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1. (WO2010081788) PROCESS FOR THE PREPARATION OF N-[5-(3-DIMETHYLAMINO-ACRYLOYL)-2-FLUORO-PHENYL]-N-METHYL-ACETAMIDE
Latest bibliographic data on file with the International Bureau

Pub. No.: WO/2010/081788 International Application No.: PCT/EP2010/050235
Publication Date: 22.07.2010 International Filing Date: 11.01.2010
IPC:
C07C 231/12 (2006.01) ,C07C 233/33 (2006.01) ,C07C 233/43 (2006.01) ,C07D 487/04 (2006.01)
C CHEMISTRY; METALLURGY
07
ORGANIC CHEMISTRY
C
ACYCLIC OR CARBOCYCLIC COMPOUNDS
231
Preparation of carboxylic acid amides
12
by reactions not involving the formation of carboxamide groups
C CHEMISTRY; METALLURGY
07
ORGANIC CHEMISTRY
C
ACYCLIC OR CARBOCYCLIC COMPOUNDS
233
Carboxylic acid amides
01
having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
30
having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by doubly-bound oxygen atoms
33
with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring
C CHEMISTRY; METALLURGY
07
ORGANIC CHEMISTRY
C
ACYCLIC OR CARBOCYCLIC COMPOUNDS
233
Carboxylic acid amides
01
having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
34
having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups
42
with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring
43
having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of a saturated carbon skeleton
C CHEMISTRY; METALLURGY
07
ORGANIC CHEMISTRY
D
HETEROCYCLIC COMPOUNDS
487
Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/-C07D477/183
02
in which the condensed system contains two hetero rings
04
Ortho-condensed systems
Applicants:
INTERQUIM, S.A. [ES/ES]; Joan Buscallà, 10 E-08190 Sant Cugat Del Vallès, ES (AllExceptUS)
SALLARES ROSELL, Juan; ES (UsOnly)
MARQUILLAS, Francisco [ES/ES]; ES (UsOnly)
Inventors:
SALLARES ROSELL, Juan; ES
MARQUILLAS, Francisco; ES
Agent:
MONTSERRAT, Jané; ZBM Patents - Zea, Barlocci & Markvardsen Pl. Catalunya, 1 E-08002 Barcelona, ES
Priority Data:
P 20090008913.01.2009ES
Title (EN) PROCESS FOR THE PREPARATION OF N-[5-(3-DIMETHYLAMINO-ACRYLOYL)-2-FLUORO-PHENYL]-N-METHYL-ACETAMIDE
(FR) PROCÉDÉ DE PRÉPARATION DE N-[5-(3-DIMÉTHYLAMINO-ACRYLOYL)-2-FLUORO-PHÉNYL]-N-MÉTHYL-ACÉTAMIDE
Abstract:
(EN) The present invention relates to a new process for the preparation of N-[5-(3-dimethylamino-acryloyl)-2-fluoro-phenyl]-N-methyl-acetamide (I) in a high yield and high purity, which is an intermediate in the synthesis of compounds with affinity for GABAA receptor. In this process, N-(5-acetyl-2- fluorophenyl)-N-methyl-acetamide (VI) is reacted with an excess of N,N-dimethylformamide dimethyl acetal (NNDMF-DMA). The present invention also provides a new process for the preparation of a compound with affinity for GABAA receptor, N-{2-fluoro-5-[3-(thiophene)-2-carbonyl-pyrazolo[1,5- a]pyrimidin-7-yl]phenyl}-N-methyl-acetamide (II), which comprises the following steps: a) methylation of N-(5-acetyl-2-fluorophenyl)-N-acetamide (IV) with a methyl sulfonate, b) reaction of the resulting compound (VI) with NNDMF-DMA, and c) reaction of the resulting compound (I) with (5-amino-1H- pirazol-4-yl)thiophen-2-yl-methanone (III) in glacial acetic acid. The present invention also relates to new intermediate (VI).
(FR) La présente invention concerne un procédé inédit de préparation de N-[5-(3-diméthylamino-acryloyl)-2-fluoro-phényl]-N-méthyl-acétamide (I), un intermédiaire utilisé dans la synthèse de composés présentant une affinité pour le récepteur GABAA, ledit procédé étant caractérisé par un rendement élevé et par une grande pureté du composé obtenu. Dans ce procédé, on fait réagir du N-(5-acétyl-2-fluorophényl)-N-méthyl-acétamide (VI) avec un excès de diméthylacétal de N,N-diméthylformamide (NNDMF-DMA). La présente invention concerne également un procédé inédit de préparation d'un composé présentant une affinité pour le récepteur GABAA, le N-{2-fluoro-5-[3-(thiophène)-2-carbonyl-pyrazolo[1,5a] pyrimidin-7-yl]phényl}-N-méthyl-acétamide (II), qui comprend les étapes suivantes : a) méthylation du N-(5-acétyl-2-fluorophényl)-N-acétamide (IV) au moyen d'un sulfonate de méthyle, b) réaction du composé résultant (VI) avec du NNDMF-DMA, et c) réaction du composé résultant (I) avec de la (5-amino-1H-pirazol-4-yl)thiophèn-2-yl-méthanone (III) dans de l'acide acétique glacial. La présente invention concerne également le nouvel intermédiaire (VI).
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Designated States: AE, AG, AL, AM, AO, AT, AU, AZ, BA, BB, BG, BH, BR, BW, BY, BZ, CA, CH, CL, CN, CO, CR, CU, CZ, DE, DK, DM, DO, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, HN, HR, HU, ID, IL, IN, IS, JP, KE, KG, KM, KN, KP, KR, KZ, LA, LC, LK, LR, LS, LT, LU, LY, MA, MD, ME, MG, MK, MN, MW, MX, MY, MZ, NA, NG, NI, NO, NZ, OM, PE, PG, PH, PL, PT, RO, RS, RU, SC, SD, SE, SG, SK, SL, SM, ST, SV, SY, TH, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, ZA, ZM, ZW
African Regional Intellectual Property Organization (ARIPO) (BW, GH, GM, KE, LS, MW, MZ, NA, SD, SL, SZ, TZ, UG, ZM, ZW)
Eurasian Patent Organization (AM, AZ, BY, KG, KZ, MD, RU, TJ, TM)
European Patent Office (AT, BE, BG, CH, CY, CZ, DE, DK, EE, ES, FI, FR, GB, GR, HR, HU, IE, IS, IT, LT, LU, LV, MC, MK, MT, NL, NO, PL, PT, RO, SE, SI, SK, SM, TR)
African Intellectual Property Organization (BF, BJ, CF, CG, CI, CM, GA, GN, GQ, GW, ML, MR, NE, SN, TD, TG)
Publication Language: English (EN)
Filing Language: English (EN)
Also published as:
UY0001032382AR075009MXMX/a/2011/007323EP2387557JP2012515149US20110275809
CN102282123RU2011133958CA2747392ES2427972PT2387557MX2011007323
CL2011001702KR1020110108346CN104945272DK2387557AU2010205739IN5197/DELNP/2011
BRPI1006150