Preparation method of erlotinib intermediate, i.e., 3-aminobenzeneacetylene

A technology of aminophenylacetylene and erlotinib, which is applied in the field of preparation of erlotinib intermediates, can solve the problems of high cost and low yield, and achieve the effects of reducing manufacturing costs, promoting development, and improving atom economy

Inactive Publication Date: 2012-10-31
SUZHOU LIXIN PHARMA
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Problems solved by technology

[0018] It has been seen from the aforementioned background information that in the current method for preparing 3-aminophenylacetylene (intermediate A), e

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  • Preparation method of erlotinib intermediate, i.e., 3-aminobenzeneacetylene
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  • Preparation method of erlotinib intermediate, i.e., 3-aminobenzeneacetylene

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Embodiment Construction

[0032] The technical solution of the present invention is described in further non-limiting detail below.

[0033] A method for preparing erlotinib intermediate 3-aminophenylacetylene, the chemical formula of the erlotinib intermediate 3-aminophenylacetylene is as follows, hereinafter referred to as intermediate A;

[0034]

[0035] The method comprises the steps of: using formula I economically available industrial raw material 3-nitroacetophenone, obtaining the intermediate 1-chloride containing halogen-substituted ethylenic bond shown in formula II through Wellsmeier (Vilsmeier) reaction -1-(3-nitrophenyl)-2-(N,N-dimethylmethoxime)-yl-ethylene, the intermediate is hydrolyzed to obtain the aldehyde intermediate 1-chloro- 1-(3-nitrophenyl)-2-formaldehyde)-base-ethylene, the aldehyde intermediate of formula III is through elimination reaction, obtains the intermediate 3-nitrophenylacetylene of formula IV; The intermediate 3 of formula IV -Nitrophenylacetylene is passed thr...

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Abstract

The invention discloses a preparation method of an erlotinib intermediate, i.e., 3-aminobenzeneacetylene. The method comprises the following steps of: performing a Vilsmeier reaction on 3-nitrobenzene ethyl ketone (I) serving as an industrial raw material to obtain an intermediate, i.e., 1-chloro-1-(3-nitrobenzophenone)-2-(N,N-dimethyl formaldehyde oxime)-yl-ethylene (II) containing a halogen-substituted alkene bond; performing a dehydration reaction to obtain a formyl intermediate, i.e., 1-chloro-1-(3-nitrobenzophenone)-2-formaldehyde)-yl-ethylene (III); performing an elimination reaction to obtain an intermediate, i.e., 3-nitrophenylacetylene (IV); and performing a nitro reduction reaction on the intermediate, i.e., 3-nitrophenylacetylene (IV) to obtain the erlotinib intermediate, i.e., 3-aminobenzeneacetylene (intermediate A). The preparation method can contribute to improving the atom economy, process simplicity and environment friendliness, so that the the erlotinib intermediate, i.e., 3-aminobenzeneacetylene can be prepared easily and conveniently.

Description

technical field [0001] The invention relates to a preparation method of an erlotinib intermediate, in particular to a preparation method of the erlotinib intermediate 3-aminophenylacetylene. Background technique [0002] Erlotinib (Erlotinib) is a new antagonist of epidermal growth factor receptor-tyrosine kinase (EGFR-TK), which was approved by the US Food and Drug Administration (FDA) and the European Medicines Agency ( EMEA) approval in the United States and EU countries, as a second-line or third-line drug for the treatment of patients with advanced or non-small cell lung cancer (NSCLC) who have failed other treatment options. The US Food and Drug Administration also approved it for the treatment of pancreatic cancer on September 13, 2005. It is now listed in seventy to eighty countries around the world. In 2007, the State Food and Drug Administration (SFDA) approved the listing of Erlotinib Hydrochloride preparations in my country. [0003] The medicinal active ingre...

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Application Information

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IPC IPC(8): C07C211/45C07C209/36
Inventor 许学农包志坚舒亮张青张爱青王喆
Owner SUZHOU LIXIN PHARMA
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