Synthesis method of tert butyl-7-(hydroxymethyl)-7, 8-dihydrogen-4H-pyrazolo diazepine-5(6H)-formyl ester

A technology of a diazepine and a synthetic method, applied in the field of synthesis of tert-butyl-7-hydroxymethyl-7,8-dihydro 4H pyrazolodiazepine 5(6H) formate, reaches Reasonable reaction process design and the effect of saving synthesis cost

Active Publication Date: 2017-09-29
上海药明康德新药开发有限公司 +4
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  • Synthesis method of tert butyl-7-(hydroxymethyl)-7, 8-dihydrogen-4H-pyrazolo diazepine-5(6H)-formyl ester
  • Synthesis method of tert butyl-7-(hydroxymethyl)-7, 8-dihydrogen-4H-pyrazolo diazepine-5(6H)-formyl ester
  • Synthesis method of tert butyl-7-(hydroxymethyl)-7, 8-dihydrogen-4H-pyrazolo diazepine-5(6H)-formyl ester

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Embodiment 1

[0009] Synthesis of N-((1H-pyrazol-3-yl)methyl)-1-phenylmethylamine

[0010]

[0011] 200 g of 1 was added to 1.5 liters of absolute ethanol solution, 25 o Add 223 grams of benzylamine and 5 grams of acetic acid to C, and stir at 25°C for 2 hours, then add 196 grams of sodium cyanoborohydride in batches at 25°C, and continue to stir the reaction system for 13 hours. The reaction system was quenched with 200 ml of saturated ammonium chloride solution, concentrated in vacuo to remove the organic phase, extracted with dichloromethane (500 ml*5), dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to obtain 400 g of crude compound 2 yellow Oil.

Embodiment 2

[0013] Synthesis of ethyl 5-benzyl-5,6,7,8-tetrahydro-4H-pyrazolo[1,5-a][1,4]diazepine-7-carboxylate

[0014]

[0015] Dissolve 449 g of compound 2 in 2 liters of ethanol solution, add 463 g of compound 3 at 10°C, stir at 25°C for 12 hours, and then stir at 70°C for 12 hours. After the reaction, the reaction solution was cooled to 20° C., concentrated in vacuo to obtain a crude product, which was then purified by a silica gel column and recrystallized from 3 liters of ethyl acetate to obtain a white compound 4 with a two-step yield of 20%.

Embodiment 3

[0017] Synthesis of ethyl 5,6,7,8-tetrahydro-4H-pyrazolo[1,5-a][1,4]diazepine-7-carboxylate

[0018]

[0019] Dissolve 80 g of compound 4 in 0.8 liter of absolute ethanol solution, add 20 g of 10% palladium carbon, and replace with hydrogen three times. The reaction was stirred at 50°C for 10 hours in the presence of 50 Psi hydrogen. After the reaction, the reaction system was filtered through diatomaceous earth to obtain an ethanol solution of Compound 5. used directly in the next reaction.

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Abstract

The present invention relates to a synthesis method of tert butyl-7-(hydroxymethyl)-7, 8-dihydrogen-4H-pyrazolo[1,5-a][1,4] diazepine-5(6H)-formyl ester, and mainly solves the technical problems of low imperfect rate, no easiness in control of reaction, experimental operation inconvenience and the like of a middle-yield route of the synthesis process in the prior art. The tert butyl-7-(hydroxymethyl)-7, 8-dihydrogen-4H-pyrazolo[1,5-a][1,4] diazepine-5(6H)-formyl ester is prepared from raw material1H-pyrazole-3-formaldehyde which is cheap and easily available and capable of large-scale production by five steps, synthesis cost is saved, and mass production can be realized. The reaction formula is as shown in the specification, and the product obtained by the method is a useful intermediate or product for synthesis of many pharmaceuticals.

Description

technical field [0001] The present invention relates to a synthetic method of tert-butyl-7-hydroxymethyl-7,8-dihydro 4H pyrazolodiazepine 5(6H) formate, i.e. tert-butyl-7-(hydroxymethyl) - Synthesis of 7,8-dihydro-4H-pyrazolo[1,5-a][1,4]diazepine-5(6H)-formyl ester. Background technique [0002] tert-Butyl-7-(hydroxymethyl)-7,8-dihydro-4H-pyrazolo[1,5-a][1,4]diazepine-5(6H)-carboxylate ( CAS: 1251014-84-2) and related derivatives have important applications in medicinal chemistry and organic synthesis and have excellent prospects. However, there is no complete synthetic route report so far. Therefore, it is of great significance to develop a synthetic method that is easy to obtain cheap raw materials, easy to operate, easy to control the reaction in batch production, and suitable for the overall yield. Contents of the invention [0003] The purpose of the present invention is to develop a kind of tert-butyl-7-(hydroxymethyl)-7,8-dihydro-4H-pyrazolo[1 ,5-a][1,4]diazepin...

Claims

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Application Information

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IPC IPC(8): C07D487/04
CPCC07D487/04
Inventor 徐学芹周强于凌波王瑞琪刘月领何燕平焦家盛安自强吴艳徐富军马汝建
Owner 上海药明康德新药开发有限公司
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