N,N-substituent-1-(1H-pyrazole-3-yl) methylamine and preparation method thereof

A technology of pyrazole and methylamine, applied in the N field, can solve problems such as rare raw materials, and achieve the effects of easy availability of raw materials and simple operation

Inactive Publication Date: 2010-04-14
SOUTHEAST UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0011] In addition, the patent also provides a third method for preparing 3-substituted-pyrazole derivatives, which also has the problem of rare raw materials

Method used

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  • N,N-substituent-1-(1H-pyrazole-3-yl) methylamine and preparation method thereof
  • N,N-substituent-1-(1H-pyrazole-3-yl) methylamine and preparation method thereof
  • N,N-substituent-1-(1H-pyrazole-3-yl) methylamine and preparation method thereof

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Embodiment 14

[0043] The preparation of embodiment 14-(dimethylamino)-1,1-dimethoxybutyl-3-ene-2-one (formula II)

[0044] Mix 1,2-propanediketal (130g, 1.1mol) and 1,1-dimethoxy-N,N-dimethylmethylamine (134g, 1.1mol) and react at 100°C for 2h. After cooling, it was concentrated to give 4-(dimethylamino)-1,1-dimethoxybutyl-3-en-2-one (II) (144 g, 76%) as a red oil. 1 H NMR (CDCl 3 , 300MHz), 3.1 (d, 6H), 3.4 (s, 6H), 4.56 (s, 1H), 5.34 (d, 1H), 7.74 (d, 1H).

Embodiment 23

[0045] The preparation of embodiment 23-(dimethoxymethyl)-1H-pyrazole (formula III)

[0046] Add II (144g, 0.83mol) to hydrazine hydrate (83.2g, 1.66mol) and react at room temperature for 24h. Washed with saturated brine (50ml×3), extracted with ethyl acetate (40ml×3), dried over anhydrous sodium sulfate, concentrated to obtain 3-(dimethoxymethyl)-1H-pyrazole ( III) (113 g, 95%). 1 H NMR (CDCl 3 , 300MHz), δ7.58 (1H, d), 6.34 (1H, d), 5.62 (1H, s), 3.37 (6H, s).

Embodiment 31

[0047] The preparation of embodiment 31H-pyrazole-3-formaldehyde (formula IV)

[0048] Mix III (116g, 0.83mol), acetic acid (25g, 0.41mol) and water (100ml) and react at room temperature for 48h. Filter and dry to obtain the dimer of 1H-pyrazole-3-carbaldehyde as a yellow solid, add the dimer to pyrimidine (200ml) heated to 50°C and stir until completely dissolved to obtain 1H-pyrazole-3-carbaldehyde monomer solution (IV) (68 g, 87%). 1 H NMR (Pyridine-d 6 , 300MHz), δ10.38 (1H, t), 7.95 (1H, dd), 7.06 (1H, d).

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Abstract

The invention relates to a method for preparing N,N-substituent-1-(1H-pyrazole-3-yl) methylamine, which is realized in a way that: in the presence of a reducing agent, a compound V disclosed in the specification reacts in an organic solvent to obtain a compound disclosed as a formula A. The method is safe and simple, and is suitable for large-scale production. R1, R2 and R3 are substituent groups.

Description

technical field [0001] The present invention relates to N, N-substituted-1-(1H-pyrazol-3-yl)methanamines, their intermediates and their synthesis methods. Background technique [0002] N,N-substituted-1-(1H-pyrazol-3-yl)methanamine (such as formula A) is an intermediate of some anti-HIV drugs and anti-inflammatory drugs (US2002383509). [0003] [0004] The preparation method of N, N-substituted-1-(1H-pyrazol-3-yl)methanamine derivatives can be found in US 2004186292; WO2006026305; Tetrahedron, 64(33), 7745, 2008; Synthetic Communications, 25(5), 761, 1995; Journal of the Chemical Society, Chemical Communications, (13), 528, 1975, etc. [0005] Among the methods of N,N-substituted-1-(1H-pyrazol-3-yl)methanamine, the method of patent US2004186292 is widely used. In the method, substituted alkyne is used as a raw material, and a substituent diazomethane is cyclo-added, and one-step reaction is performed to obtain N, N-substituted-1-(1H-pyrazol-3-yl)methanamine. However, ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D231/12
Inventor 杨池徐春祥王明亮
Owner SOUTHEAST UNIV
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