Analyzing the synthesis route of 5-(Furan-2-yl)-1H-pyrazol-3-amine

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3- Ethynylaniline (146 mg, 1.25 mmol) and DIPEA (0. 22 mL, 1.25 mmol) were added to a solution of cyanuric chloride (230 mg, 1.25 mmol) in THF (16 mL) at 0 0C. The reaction mixture was stirred at 0 C to room temperature for 2 hours. 3-amino-5-(2-furyl) pyrazole (187 mg, 1.25 mmol) and DIPEA (0.22 mL, 1.25 mmol) were added to the above mixture and the resulting mixture was heated with microwave initiator at 150 C for 10 minutes. 1 -methylpiperazine (0.28 mL, 2.50 mmol) and DIPEA (0.44 mL, 2.50 mmol) were added to the mixture and the mixture was heated with microwave initiator at 60 0C for 10 minutes. Saturated NaHCO3 in water was added and the mixture was extracted by ethyl acetate (3 x 50 mL). The combined organic was washed by brine, dried over sodium sulfate and concentrated. The residue was chromatographed on a silica gel column and eluted with 0- 5 % MeOH/DCM which afforded compound 36 as light brown solid (130 mg, 24%). 1H NMR (400 MHz, DMSO-d6) delta 12.75 (bs, IH, NH), 10.19-9.44 (m, 2H, NH), 7.83- 6.06 (m, 8H, Ar- H), 4.14-4.04 (m, IH, CH), 3.77 (s, 4H, 2CH2), 2.37 (s, 4H, 2CH2), 2.22 (s, 3H, CH3); ESI- MS: calculated for (C23H23N9O) 441 , found 442 [M+H]+. HPLC: retention time: 15.31 min. purity: 95%.

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Example 23To a solution of cyanuric chloride (230 mg, 1.25 mmol) in THF (16 mL) was added cumylamine (0.18 mL, 1.25 mmol) and DIPEA (0. 20 mL, 1.25 mmol) at 0 C. The reaction mixture was let to stir at 0 C to room temperature for 2h. 3-amino-5-(2- furyl)pyrazole (187 mg, 1.25 mmol) and DIPEA (0.20 mL, 1.25 mmol) were added to the above mixture and the resulting mixture was heated with microwave initiator at 150 C for 10 minutes. 1 -methylpiperazine (0.28 mL, 2.50 mmol) and DIPEA (0.44 mL, 2.50 mmol) were added to the mixture and the mixture was heated with microwave initiator at 60 C for 10 minutes. Saturated NaHCO3 in water was added and the mixture was extracted by ethyl acetate (3 x 50 mL). The combined organic was washed by brine, dried over sodium sulfate and concentrated. The residue was chromatographed on a silica gel column eluted with 0-5 % MeOH/DCM afforded 23 as light brown solid (140 mg, 24%). 1H NMR (400 MHz, DMSO-d6) delta 12.88 (bs, 1H, NH), 9.87 (bs, 1Eta, NH), 7.88 (bs, 1Eta,NH), 7.67-5,91 (m, 9Eta, Ar-H), 3.52-3.20 (m, 4Eta, 2CH2), 2.32-1.96 (m, 7Eta, 2CH2, CH3), 1.67 (s, 3Eta, CH3), 1.49 (s, 3Eta, CH3); ESI-MS: calcd for (C24Eta29N9O) 459, found 460 [M+H]+. HPLC: retention time: 19.16 min. purity: 99%.

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EXAMPLE 22 6-(2-Furyl)-1H-imidazo[1,2-b]pyrazole A solution of 2.0 g of 5-(2-furyl)-3-aminopyrazole in 5 ml of dimethylformamide was slowly added dropwise at room temperature, whilst stirring, to 0.59 g of a 55% w/w suspension of sodium hydride in mineral oil, which itself was suspended in 15 ml of dimethylformamide, and the resulting mixture was stirred for 1 hour at room temperature. 2.7 g of 2,2-dimethoxyethyl bromide were then added, and the mixture was allowed to react at 60 to 70 C. for 4 hours. At the end of this time, the resulting mixture was partitioned between ethyl acetate and water. The organic layer was washed with water and dried over anhydrous magnesium sulfate. The solvent was then removed by evaporation under reduced pressure. The residue was purified by silica gel column chromatography using a 1:1 by volume mixture of ethyl acetate and hexane as the eluent, to afford 1.2 g of an intermediate compound as an oil. A mixture of 1.2 g of this intermediate compound, 10 ml of a 4N solution of hydrogen chloride in dioxane and 4 ml of ethanol was heated under reflux for 20 minutes, after which the reaction mixture was poured into ice water and made basic by the addition of aqueous ammonia. The mixture was then extracted with ethyl acetate. The extract was washed with an aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate, after which the solvent was removed by evaporation under reduced pressure. The residue was purified by silica gel column chromatography using a 1:1 by volume mixture of ethyl acetate and hexane as the eluent, and the product was recrystallized from a mixture of ethyl acetate and hexane, to afford 0.44 g of the title compound as pale brown needle-like crystals, melting at 186 to 188 C. Elemental analysis: Calculated for C9 H7 N3 O: C, 62.42%; C, 4.07%; N, 24.27%. Found: C, 62.36%; H, 4.23%; N, 24.14%.

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Electric Literature of 96799-02-9,Some common heterocyclic compound, 96799-02-9, name is 5-(Furan-2-yl)-1H-pyrazol-3-amine, molecular formula is C7H7N3O, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

To a solution of cyanuric chloride (300 mg, 1.63 mmol) in THF (16 mL) was added thiophenol (0.17 mL, 1.63 mmol) and DIPEA (0.28 mL, 1.63 mmol) at 0 C. The reaction mixture was stirred at 0 0C to room temperature for 2 hours. After starting material was consumed, 3-amino-3(2-furyl)pyrazole (243 mg, 1.63 mmol) and DIPEA (0.28 mL, 1.63 mmol) was added at O C. The mixture was stirred at room temperature for 3 additional hours. 1-methylpiperazine (0.27 mL, 2.45 mmol) and DlPEA (0.43 mL, 2.45 mmol) were added to the above mixture and allowed to stir at room temperature for overnight. Saturated NaHCC>;3 in water was added and the mixture was extracted by ethyl acetate. The combined organic was washed by brine, dried over sodium sulfate and concentrated. The residue was chromatographed on a silica gel column eluted with 0-5 % MeOH/DCM to afford compound 9 as light yellow solid (100 mg, 14 %). IH NMR (400 MHz, DMSO-d6) delta 12.69 (bs, IH, NH), 9.79 (s, IH, NH), 7.79 (bs, I H, NH), 7.61 (bs, 2H, Ar-H), 7.45 (s, 3H, Ar-H), 6.60 (s-lH, Ar-H), 5.98 (bs,lH, Ar-H), 3.70 (bs, 4H, 2CH2), 2.31 (bs, 4H, 2CH2), 2.18 (s, 3H,CH3); ESl -MS: calculated for (C2,H22N80S) 434, found 435 [M+H]+. HPLC: retention time: 18.68 min. purity: 99%.

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Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 96799-02-9.

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 96799-02-9, name is 5-(Furan-2-yl)-1H-pyrazol-3-amine, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 96799-02-9

General procedure: A mixture of aldehyde (1.5 mmol), amine (3 mmol) and p-toluenesulphonic acid monohydrate (0.011 g, 0.06 mmol) in ethanol (10 mL) was heated to reflux for 2 h. After cooling, the precipitate was filtered off, washed with a little cold ethanol and dried in vacuo over anhydrous CaCl2.

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DIPEA (0.13 mL, 0.65 mmol) and 5-(furan-2-yl)-lH-pyrazol-3-amine (87.4 mg, 0.586 mmol) were added to a suspension of compound 4 (0.2g, 0.588 mmol) in THF (12 mL). The mixture was heated at 150 C for 10 minutes using microwave initiator. A solution of N-Methylpiperazine (70.4 mg, 0.703 mmol) and DIPEA ((0.13 mL, 0.65 mmol) in THF (5 mL) was added to the above vial at room temperature. The mixture was heated at 60 0C for 0.2 hours. After cooling to room temperature, saturated NaHCO3 in water was added to the flask and the mixture was extracted with dichloromethane (3 x25 ml) and washed by brine, dried over sodium sulfate and concentrated. The resulting crude product was purified by Teledyne-Isco flash system by using DCM/MeOH, 0 to 15% of Methanol in dichloromethane to provide compound 30 as light yellow solids (155 mg, 32%). 1 H NMR (400 MHz, DMSO- d6) delta 12.66 (bs, I H), 10.37 (s, IH), 9.79 (s, IH), 7.797.06 (m, 7H1), 6.07 (bs, IH), 3.70 (m, 4H), 2.33 (m, 4H), 2.20 (s, 3H), 1.42 (m, I H), 0.85 (m, 4H) ; ESI-MS: calculated for (C25H27N9O2S) 517, found 518 (MH+). HPLC: retention time: 10.92 min. purity: 96%.

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96799-02-9, name is 5-(Furan-2-yl)-1H-pyrazol-3-amine, belongs to pyrazoles-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Application In Synthesis of 5-(Furan-2-yl)-1H-pyrazol-3-amine

General procedure: The general method was described for the synthesis of D1. Compound C1 (150 mg, 0.393 mmol) was dissolved in ethanol (2 mL),followed by addition of 5-phenyl-1H-pyrazol-3-amine (62.63 mg, 0.393 mmol) and triethylamine (119.43 mg, 1.18 mmol). The mixture was stirred at room temperature for 5 h. The resultant mixture was purified by column chromatography to give D1.

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EXAMPLE 7 3-[(5-Furan-2-yl-1H-pyrazol-3-ylamino)-methylene]-4-methyl-1,3-dihydro-indol-2-one The named compound is prepared by substituting E & Z-3-[(hydroxy)-methylene]-4-methyl-1,3-dihydro-indol-2-one for E & Z-3-[(hydroxy)-methylene]-1,3-dihydro-indol-2-one and substituting 3-amino-5-(2-furyl)-pyrazole for 3-aminopyrazole in the reaction of Example 1. Specifically, E & Z-3-[(hydroxy)-methylene]-4-methyl-1,3-dihydro-indol-2-one (0.110 gms.) is reacted with 0.2065 gms. of 3-amino-5-(2-furyl)-pyrazole by refluxing in tetrahydrofuran (2.5 mL).

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To a cold solution of 5-amino-3-(2-furyl)pyrazole (1.00 g g, 6.70 mmol) in THF (20 ml) was added a suspension of sodium hydride (60% in mineral oil, 322 mg, 8.05 mmol) in THF (6 ml) at 0 C. slowly. After stirring at 0 C. for 30 minute, di-tert-butyldicarboxate (1.61 g, 7.38 mmol) was added. The mixture was stirred at 0 C. for 75 minutes. TLC was checked and the starting material was consumed. The reaction mixture was quenched with ice-water, extracted with ethyl acetate/Hexane (90/10, 25 ml x 2). The combined organic was washed by brine, dried over sodium sulfate and concentrated. The residue was triturated with EtOAc (5 ml)-Hexanes (30 ml). The yellow solids were collected by filtration, washed by hexanes to give compound 7 (1.41 g, 84% yield). 1H NMR (400 MHz, DMSO-d6) delta: 7.69 (m, 1H), 6.77 (m, 1H), 6.53 (m, 1H), 6.40 (br, 2H), 5.56 (s, 1H), 1.55 (s, 9H).

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The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 96799-02-9, name is 5-(Furan-2-yl)-1H-pyrazol-3-amine, A new synthetic method of this compound is introduced below., Application In Synthesis of 5-(Furan-2-yl)-1H-pyrazol-3-amine

A solution of 3-amino-5-(2-furyl)pyrazole (162 mg, 1.09 mmol) and DIPEA (0.19 mL, 1.09 mmol) in THF (5 mL) was added dropwise to a solution of cyanuric chloride (200 mg, 1.09 mmol) in THF (16.0 mL) at 0 0C. The reaction mixture was stirred at 0 C to room temperature for 2 hours. Then, 1-metyl piperazine (0.12 mL, 1.09 mmol) and DlPEA (0.19 mL, 1.30 mmol) were added to the mixture. The mixture was allowed to stir at room temperature for 3 hours. The solids were filtered off to give compound 11 as white solid (1 10 mg, 14 %). %). 1H NMR (400 MHz, DMSOd6) delta 12.92 (s, IH, NH), 10.38 (s, IH, NH), 7.76 (s, IH, Ar-H), 6.816.61 (m, 3H, Ar-H), 3.77-3.72 (m, 4H, 2CH2), 2.38-2.35 (m, 4H, 2CH2), 2.21 (2, 3H, CH3); ESI-MS: calculated for (C15Hi7ClN8O) 360, found 361 [M+H]+.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.