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Type | HazMat fee for 500 gram (Estimated) |
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Structure of 1225387-53-0
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
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Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
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CAS No. : | 1225387-53-0 |
Formula : | C3H5N3 |
M.W : | 83.09 |
SMILES Code : | NC1=CC=NN1 |
MDL No. : | MFCD31727672 |
InChI Key : | JVVRJMXHNUAPHW-UHFFFAOYSA-N |
Pubchem ID : | 74561 |
GHS Pictogram: |
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Signal Word: | Danger |
Hazard Statements: | H302-H314-H317 |
Precautionary Statements: | P280-P305+P351+P338-P310 |
Class: | 8 |
UN#: | 3267 |
Packing Group: | Ⅱ |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | In acetic acid; at 90℃; | A suspension of lH-pyrazol-5-amine (0.804 g, 9.48 mmol) and sodium nitromalonaldehyde monohydrate (1.56 g, 9.96 mmol) in acetic acid (12 mL) was heated to 9O0C overnight. The reaction mixture was cooled to room temperature and poured into water (50 mL). The resulting solids were collected by filtration. The solids were washed with water (3 X 20 mL) and dried in vacuo to give 5-nitro-l H-pyrazolo [3 ,4-b]pyridine (1.40 g, 84%) as a solid. |
84% | In acetic acid; at 90℃; | A suspension of lH-pyrazol-5 -amine (0.804 g, 9.48 mmol) and sodium nitromalonaldehyde monohydrate (1.56 g, 9.96 mmol) in acetic acid (12 mL) was heated to 90C overnight. The reaction mixture was cooled to room temperature and poured into water (50 mL). The resulting solids were collected by filtration. The solids were washed with water (3 X 20 mL) and dried in vacuo to give 5-nitro-lH-pyrazolo[3,4-b]pyridine (1.40 g, 84%) as a solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With caesium carbonate; In N,N-dimethyl-formamide; at 110℃;Inert atmosphere; | The compound 5-aminopyrazole (5 g, 60 mmol)And <strong>[1001-26-9]ethyl 3-ethoxyacrylate</strong> (13 g, 90 mmol)Cesium carbonate (29 g, 90 mmol)Was mixed in 100 ml of N, N-dimethylformamide,The reaction was heated to 110 ° C overnight.Cooled to room temperature, diluted with 200 ml of water,Ether extraction (40 mL x 3), the aqueous phase was concentrated under reduced pressure,The residue was purified by silica gel column chromatography (DCM: MeOH = 10: 1)4H-pyrazolo [1,5-a] pyrimidin-5-one (8 g) in 99percent yield. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Treatment of commercially available aminopyrazole 1 with di-tert-butyl-dicarbonate affords compound 2. Oxidation of 2 with dibenzoyl peroxide and KOH (U.S. Pat. No. 4,945,166) produces 1-hydroxypyrazole 3. Reaction of 3 with methyl iodide and N,N-diisopropylethylamine gives 1-methoxypyrazole 4 (J. Org. Chem. 1995, 60, 4995). Nitrosation of 4 with isoamyl nitrite produces the nitroso compound 5. Hydrogenation of 5 with Pd/C under hydrogen gives compound 6. Deprotection of 6 with 2N-HCl in 1,4-dioxane results in the formation of 2-Methoxy-2H-pyrazole-3,4-diamine 7. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
32% | In methanol; for 16h;Heating / reflux; | Step A. <strong>[25007-54-9]Dimethyl 2-oxosuccinate</strong> (6.05 g, 37.8 mmol) and lH-pyrazol-3 -amine (3.14 g, 37.8 mmol) was heated to reflux in methanol (55 mL) for 16 h. After cooling down, the solid was collected by filtration and washed with methanol to afford methyl 7-hydroxypyrazolo[l,5-a]pyrimidine-5-carboxylate (2.32 g, 32%) as yellow solid. [MH]+ = 194.0. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride; copper(l) chloride; isopentyl nitrite; In water; acetonitrile; at 0 - 20℃; for 180h;Inert atmosphere; | To a souUon of 1H-pyrazo-5-amne (23.6 g, 284 mmo) n CH3CN (1 L) under a nitrogen atmosphere were added HC (140 m, 1420 mmo, 32%) and copper chorde (56.3 g, 568 mmo) at 0C, sopenty ntrte (80 mL 568 mmo) was added at 0C and the mixture was stirred at 0C for 2 days. sopenty nitrite (20 m, 0.5 eq) was added and the mixture was stirred at RT for another 5.5 days. The reaction mixture was sowy poured into ammonium hydroxide (1 L, 25%) and extracted with AcOEt. The organic phase was separated and the aqueous phase was extracted with AcOEt. The combined organic ayers were washed with brine, dried over Na2SO4 and concentrated. The crude product was purified by sWca ge co?umn chromatography (hexane / TBME from 1:0 to 4:6) to afford 5-choro-1H-pyrazoe. Mz = 103/105 [M+H]+, Rt = 0.48 mm (UPLC Method B2), 1H NMR (600 MHz, DMSO-d6) : 6 ppm: 1300 (bs, IH), 7.79 (t, IH), 6.29 (t, IH), isoarny acoho :4.28 (t, IH), 3.41 (q, 2H), 1.30 (q, 2H), 0.85 (d, 6H). |