AR077821A1 - PROCEDURE TO PREPARE 4-METHYL-3-TIENYLAMINE HYDROCLORIDE - Google Patents

PROCEDURE TO PREPARE 4-METHYL-3-TIENYLAMINE HYDROCLORIDE

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Publication number
AR077821A1
AR077821A1 ARP100102909A AR077821A1 AR 077821 A1 AR077821 A1 AR 077821A1 AR P100102909 A ARP100102909 A AR P100102909A AR 077821 A1 AR077821 A1 AR 077821A1
Authority
AR
Argentina
Prior art keywords
methyl
amino
thiophene
mixture
base
Prior art date
Application number
Other languages
Spanish (es)
Original Assignee
Sanofi Aventis Us Llc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Sanofi Aventis Us Llc filed Critical Sanofi Aventis Us Llc
Publication of AR077821A1 publication Critical patent/AR077821A1/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D333/30—Hetero atoms other than halogen
    • C07D333/36—Nitrogen atoms

Abstract

util para preparar 3-cloro-3N-(2-benzimidazolil)-4-metil-3-tienilamina que posee propiedades inhibidoras sobre el intercambiador sodio/protones de subtipo 3 (NHE-3). Reivindicacion 1: Un procedimiento para preparar hidrocloruro de 3-amino-4-metiltiofeno, que comprende: (a) reaccionar un éster 3-amino-4-metil-tiofeno-2-carboxilato de alquilo(C1-6) con una solucion acuosa de una primera base adecuada, en presencia de un disolvente adecuado para obtener 3-amino-4-metil-tiofeno-2-carboxilato; (b) anadir la mezcla de reaccion de la etapa (a) que contiene 3-amino-4-metil-tiofeno-2-carboxilato a una solucion acuosa de un ácido adecuado para obtener 3-amino-4-metil-tiofeno en el que la cantidad de ácido adecuado sea suficiente para mantener el pH de la mezcla resultante a o por debajo de 1 después de anadir la mezcla de reaccion de la etapa (a); (c) anadir la mezcla de reaccion de la etapa (b) que contiene 3-amino-4-metil-tiofeno a una mezcla de una segunda base adecuada y un disolvente orgánico adecuado en el que la cantidad de la segunda base adecuada sea suficiente para mantener el pH de la mezcla resultante a o por debajo de 13 después de anadir la mezcla de, reaccion de la etapa (b); (d) separar la fase orgánica y la fase acuosa; y (e) anadir la fase orgánica al ácido hidroclorico.useful for preparing 3-chloro-3N- (2-benzimidazolyl) -4-methyl-3-thienylamine having inhibitory properties on the sodium / proton exchanger of subtype 3 (NHE-3). Claim 1: A process for preparing 3-amino-4-methylthiophene hydrochloride, comprising: (a) reacting an alkyl (C1-6) alkyl 3-amino-4-methyl-thiophene-2-carboxylate ester with an aqueous solution of a suitable first base, in the presence of a suitable solvent to obtain 3-amino-4-methyl-thiophene-2-carboxylate; (b) adding the reaction mixture from step (a) containing 3-amino-4-methyl-thiophene-2-carboxylate to an aqueous solution of a suitable acid to obtain 3-amino-4-methyl-thiophene in the that the amount of acid suitable is sufficient to maintain the pH of the resulting mixture at or below 1 after adding the reaction mixture of step (a); (c) adding the reaction mixture of step (b) containing 3-amino-4-methyl-thiophene to a mixture of a suitable second base and a suitable organic solvent in which the amount of the appropriate second base is sufficient to maintain the pH of the resulting mixture at or below 13 after adding the mixture, reaction of step (b); (d) separating the organic phase and the aqueous phase; and (e) add the organic phase to hydrochloric acid.

ARP100102909 2009-08-11 2010-08-09 PROCEDURE TO PREPARE 4-METHYL-3-TIENYLAMINE HYDROCLORIDE AR077821A1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US23293409P 2009-08-11 2009-08-11

Publications (1)

Publication Number Publication Date
AR077821A1 true AR077821A1 (en) 2011-09-28

Family

ID=42735468

Family Applications (1)

Application Number Title Priority Date Filing Date
ARP100102909 AR077821A1 (en) 2009-08-11 2010-08-09 PROCEDURE TO PREPARE 4-METHYL-3-TIENYLAMINE HYDROCLORIDE

Country Status (3)

Country Link
AR (1) AR077821A1 (en)
TW (1) TW201120025A (en)
WO (1) WO2011019680A1 (en)

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS4412895B1 (en) * 1967-09-08 1969-06-10
US7049333B2 (en) 2002-06-04 2006-05-23 Sanofi-Aventis Deutschland Gmbh Substituted thiophenes: compositions, processes of making, and uses in disease treatment and diagnosis
CN101679405A (en) * 2007-03-23 2010-03-24 阵列生物制药公司 2-aminopyridine analogs as glucokinase activators
DE602008002440D1 (en) * 2007-06-28 2010-10-14 Sanofi Aventis Us Llc PROCESS FOR PREPARING N- (2-CHLORO-4-METHYL-3-THIENYL) -1H-BENZIMIDAZOLE-2-AMINE HYDROCHLORIDE AND INTERMEDIATES THEREFOR

Also Published As

Publication number Publication date
WO2011019680A1 (en) 2011-02-17
TW201120025A (en) 2011-06-16

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