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Optically-active cyclopropane hydrazide compound, and preparation method and application thereof

A compound, a technology of ethyl cyclopropylcarboxylate, applied in the field of cyclopropane acyl hydrazide compounds and their preparation, can solve problems such as potential safety hazards, explosiveness and the like

Active Publication Date: 2014-02-19
SHANGHAI INST OF PHARMA IND +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

But NaN 3 It is a highly toxic reagent and explosive, and there is a great safety hazard in production

Method used

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  • Optically-active cyclopropane hydrazide compound, and preparation method and application thereof
  • Optically-active cyclopropane hydrazide compound, and preparation method and application thereof
  • Optically-active cyclopropane hydrazide compound, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] Preparation of (1R, 2S)-2-(3,4-difluorophenyl)-cyclopropylformylcarbamide (compound of formula (1))

[0048] Ethyl (1R,2S)-2-(3,4-difluorophenyl)-cyclopropylcarboxylate (4) (prepared as described in Example 3 of WO2008018822) (85 g) was dissolved in isopropanol (2 L) middle. 85% hydrazine hydrate (0.5 L) was added, and the reaction was heated under reflux for 5 hours. After cooling down to room temperature, add water (6L), filter, wash the filter cake with a small amount of isopropanol and water, and dry to obtain a white solid (1R,2S)-2-(3,4-difluorophenyl)-cyclopropylmethyl Acyl trap (70g, yield 87.8%). m / z(M + )212

[0049] 1HNMR(DMSO-d6)δ1.21-1.25(m, 1H), 1.30-1.38(m, 1H), 1.75-1.80(m, 1H), 2.26-2.30(m, 1H), 4.20(s, 2H) , 6.93-7.07(m, 1H), 7.09-7.20(m, 1H), 7.21-7.27(m, 1H), 9.13(s, 1H).

Embodiment 2

[0051] Preparation of (1R, 2S)-2-(3,4-difluorophenyl)-cyclopropylformylcarbamide (compound of formula (1))

[0052] Ethyl (1R,2S)-2-(3,4-difluorophenyl)-cyclopropylcarboxylate (4) (15 g) was dissolved in absolute ethanol (400 mL). 40% hydrazine hydrate (350 mL) was added, followed by heating under reflux for 3.5 hours. After cooling down to room temperature, add water (500mL), filter, wash the filter cake with a small amount of ethanol and water, and dry to obtain a white solid (1R,2S)-2-(3,4-difluorophenyl)-cyclopropylformyl Trap (11.9 g, 84.6% yield).

Embodiment 3

[0054] Preparation of (1R, 2S)-2-(3,4-difluorophenyl)-cyclopropylformylcarbamide (compound of formula (1))

[0055] Ethyl (1R,2S)-2-(3,4-difluorophenyl)-cyclopropylcarboxylate (4) (170 g) was dissolved in absolute ethanol (4 L). 85% hydrazine hydrate (1.7 L) was added, followed by heating to reflux for 2 hours. After cooling down to room temperature, add water (12L), filter, wash the filter cake with a small amount of absolute ethanol and water, and dry to obtain a white solid (1R,2S)-2-(3,4-difluorophenyl)-cyclopropyl Formyl trap (159.5 g, yield 100%).

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Abstract

The invention relates to an optically-active cyclopropane hydrazide compound, and a preparation method and an application thereof, concretely discloses a new compound of formula (1), and also discloses a preparation method of the compound of the formula (1), and an application of the compound of the formula (1) in the preparation of a compound of formula (2) for synthesizing an important intermediate of ticagrelor.

Description

technical field [0001] The invention relates to an optically active cyclopropane hydrazine compound and a preparation method thereof. More specifically, the present invention relates to compounds suitable for the preparation of pharmaceutical products, especially important intermediates for the synthesis of ticagrelor, their preparation methods and their applications for the preparation of ticagrelor intermediates. Background technique [0002] Thrombosis, the formation of localized blood clots, is a major cause of occurrence and death in patients with arterial diseases such as myocardial infarction and stroke, as well as venous thromboembolic diseases, including deep vein thrombosis and pulmonary embolism. At present, the clinically used antithrombotic drugs mainly include anticoagulant drugs, antiplatelet drugs and thrombolytic drugs. Commonly used antiplatelet drugs include: cyclooxygenase inhibitors, ADP (P2Y12) receptor antagonists, GP II b / IIIa receptor antagonists, e...

Claims

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Application Information

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IPC IPC(8): C07C243/36C07C241/04C07C247/22
Inventor 江华袁哲东朱雪焱王胡博
Owner SHANGHAI INST OF PHARMA IND
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