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Product Details of [ 1225387-53-0 ]

CAS No. :1225387-53-0 MDL No. :MFCD31727672
Formula : C3H5N3 Boiling Point : -
Linear Structure Formula :- InChI Key :JVVRJMXHNUAPHW-UHFFFAOYSA-N
M.W :83.09 Pubchem ID :74561
Synonyms :

Safety of [ 1225387-53-0 ]

Signal Word:Danger Class:8
Precautionary Statements:P280-P305+P351+P338-P310 UN#:3267
Hazard Statements:H302-H314-H317 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 1225387-53-0 ]

* 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.

  • Upstream synthesis route of [ 1225387-53-0 ]
  • Downstream synthetic route of [ 1225387-53-0 ]

[ 1225387-53-0 ] Synthesis Path-Upstream   1~16

  • 1
  • [ 1225387-53-0 ]
  • [ 105-53-3 ]
  • [ 57489-70-0 ]
Reference: [1] ACS Medicinal Chemistry Letters, 2010, vol. 1, # 5, p. 204 - 208
[2] Journal of Medicinal Chemistry, 2012, vol. 55, # 22, p. 10312 - 10313
  • 2
  • [ 34461-00-2 ]
  • [ 1225387-53-0 ]
  • [ 63572-73-6 ]
YieldReaction ConditionsOperation in experiment
84% 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, 84percent) as a solid.
84% 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 90°C 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, 84percent) as a solid.
Reference: [1] Patent: WO2011/25968, 2011, A1, . Location in patent: Page/Page column 49
[2] Patent: WO2009/111279, 2009, A1, . Location in patent: Page/Page column 96
[3] Chemistry of Heterocyclic Compounds (New York, NY, United States), 1992, vol. 28, # 11, p. 1335 - 1339[4] Khimiya Geterotsiklicheskikh Soedinenii, 1992, # 11, p. 1560 - 1564
[5] ACS Medicinal Chemistry Letters, 2011, vol. 2, # 5, p. 342 - 347
  • 3
  • [ 34461-00-2 ]
  • [ 1225387-53-0 ]
  • [ 63572-73-6 ]
  • [ 116835-08-6 ]
Reference: [1] Canadian Journal of Chemistry, 1988, vol. 66, # 3, p. 420-428
  • 4
  • [ 1225387-53-0 ]
  • [ 87-13-8 ]
  • [ 43024-61-9 ]
Reference: [1] Patent: EP1918291, 2008, A1, . Location in patent: Page/Page column 22
  • 5
  • [ 1225387-53-0 ]
  • [ 74-88-4 ]
  • [ 446866-62-2 ]
  • [ 1192-21-8 ]
Reference: [1] Patent: WO2005/30758, 2005, A1, . Location in patent: Page/Page column 60-61
  • 6
  • [ 83724-91-8 ]
  • [ 1225387-53-0 ]
  • [ 274-71-5 ]
Reference: [1] Patent: US5334505, 1994, A,
  • 7
  • [ 1001-26-9 ]
  • [ 1225387-53-0 ]
  • [ 29274-22-4 ]
YieldReaction ConditionsOperation in experiment
99% With caesium carbonate In N,N-dimethyl-formamide at 110℃; Inert atmosphere The compound 5-aminopyrazole (5 g, 60 mmol)And ethyl 3-ethoxyacrylate (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.
Reference: [1] Patent: CN104250252, 2017, B, . Location in patent: Paragraph 0095; 0097; 0098
[2] Journal of Organic Chemistry, 2007, vol. 72, # 3, p. 1043 - 1046
  • 8
  • [ 874-14-6 ]
  • [ 1225387-53-0 ]
  • [ 29274-22-4 ]
YieldReaction ConditionsOperation in experiment
58% With sodium ethanolate In ethanol at 60℃; for 2 h; 1,3-Dimethyl uracil (3.15 g, 22.5 mmol) and sodium ethoxide (23 mL of a 21percent solution in ethanol) were added to a solution of lH-pyrazol-5 -amine (1.7 g, 20.4 mmol) in ethanol (50 mL). The resulting mixture was heated to 60 0C for 2 h and was then cooled to room temperature. The pale brown solid was isolated by filtration to give pyrazolo[l,5-a]pyrimidin- 5(4H)-one (1.6 g, 58percent). Retention time (min) = 0.820, method [3], MS(ESI) 136.1 (M+Η).
12.50 g With sodium ethanolate In ethanol at 80℃; for 5 h; A mixture of A-5 (8.00 g, 96.28 mmol), 1,3-dimethylpyrimidine-2,4-dione (13.49 g, 96.28 mmol) and EtONa (32.76 g, 481.40 mmol) in EtOH (150 mL) was stirred at 80 °C for 5 hours. The solid was collected by filtration, washed with EtOH (50 mL), and dried in an oven to afford A-6 (12.50 g, 92.51 mmol) as a solid. 1H NMR (400MHz, DMSO-d6) δ 11 7.97 (d, 1H), 7.43 (d, 1H), 5.62 (d, 1H), 5.35 (d, 1H).
Reference: [1] Patent: WO2010/91310, 2010, A1, . Location in patent: Page/Page column 141
[2] Journal of Organic Chemistry, 2007, vol. 72, # 3, p. 1043 - 1046
[3] Patent: WO2018/98500, 2018, A1, . Location in patent: Page/Page column 84
  • 9
  • [ 922-67-8 ]
  • [ 1225387-53-0 ]
  • [ 29274-22-4 ]
Reference: [1] Patent: WO2010/63487, 2010, A1, . Location in patent: Page/Page column 68
  • 10
  • [ 1225387-53-0 ]
  • [ 934758-92-6 ]
Reference: [1] Patent: WO2015/181747, 2015, A1, . Location in patent: Page/Page column 38; 39
  • 11
  • [ 1225387-53-0 ]
  • [ 109-64-8 ]
  • [ 126352-69-0 ]
YieldReaction ConditionsOperation in experiment
36% With triethylamine In 1,4-dioxane at 110℃; for 5 h; To a solution of 1 H-pyrazol-5-amine (9.8 g, 0.1 mol) and TEA (36.0 g, 0.3 mmol) m1,4-dioxane (200 mL) was added 1,3-dibromopropane (26.3 g, 0.1 mmol). After stirring at 110°C for 5 hrs, the reaction m1xture was filtered. The filtration was concentrated to dry ness. Theresidue was purified by silica gel column (DCJ\1/MeOH = 100/1) to give 4,5,6,7-tetrahydropyrazolo[l,5-a]pyrimidine (5.3 g, yield: 36~~) as a white solid.[001020] 1H NlVIR (300 rviHz, CDCb): 8 = 7.18 (s, 1H), 5.26 (s, 1H), 4.22-4.00 (m, 3H), 3.26-3.22 (m, 2H), 2.11-2.03 (m, 2H).
Reference: [1] Patent: WO2018/136890, 2018, A1, . Location in patent: Paragraph 001018; 001019; 001020
[2] Bioorganic and Medicinal Chemistry, 1997, vol. 5, # 3, p. 557 - 567
  • 12
  • [ 123-91-1 ]
  • [ 1225387-53-0 ]
  • [ 109-64-8 ]
  • [ 126352-69-0 ]
Reference: [1] Patent: US5173485, 1992, A,
  • 13
  • [ 2065-75-0 ]
  • [ 1225387-53-0 ]
  • [ 705263-10-1 ]
YieldReaction ConditionsOperation in experiment
86% With hydrogenchloride In ethanol; water at 0 - 20℃; for 2 h; Will V be non-material (15 · lg, lOOmmol)And the formula II is not material (8.3g, lOOmmol)Placed in a 250 ml round bottom flask,Add 120 ml of ethanol,Cooled to 0 ° C, add 12ml concentrated hydrochloric acid, return to room temperature, stirring 2h,The reaction precipitated a pale yellow solid. After direct filtration, the cake was washed with saturated NaHC03 solution and then washed with water.After drying, 17 g of the intermediate represented by formula VI was obtained. The yield of the intermediate represented by formula VI was calculated to be 86percent.
30% for 2 h; Reflux The 3-aminopyrazole (2.0g, 23.9 mmol) and 20 mL of ethanol were added 100 mL three-neck flask, and stirred to dissolve, then 2-bromo-malonaldehyde (2.4 g, 16.0 mmol) was added in the flask. The system presents a reddish brown after the mixture was heated under reflux for 2 h. The reaction was cooled to room temperature and the organic solvent is evaporated to dryness. The residue was purified by column chromatography: gel (eluent petroleum ether / ethyl acetate). Pale yellow crystalline solid, yield: 30percent. 1H NMR (CDCl3, 400 MHz, δ ppm): 8.50 (d, J = 3.3 Hz, 1H), 7.99 (dd, J = 9.2, 1.5 Hz, 1H), 7.82 (s, 1H), 7.13 (dd, J = 9.2, 4.4 Hz, 1H). ESI-MS(m/z): 197.3 [M+H]+.
Reference: [1] Patent: CN105130991, 2017, B, . Location in patent: Paragraph 0037; 0041-0043
[2] Patent: WO2014/138088, 2014, A1, . Location in patent: Page/Page column 60
[3] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 15, p. 4388 - 4392
[4] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 23, p. 5830 - 5835
  • 14
  • [ 2065-75-0 ]
  • [ 1225387-53-0 ]
  • [ 705263-10-1 ]
  • [ 875781-17-2 ]
YieldReaction ConditionsOperation in experiment
2.1% at 20℃; Heating / reflux A solution of 1 H-pyrazol-5-amine x79 (25 g, 1 eq, 0.3 mol) and bromomalonaldehyde x9 (45.4 g, 1 eq, 0.3 mol) ethanol (250 ml) is refluxed for 2 hours. After cooling, the reaction mixture is stirred at room temperature overnight. The solvent is removed under reduced pressure and the crude is purified using chiral chromatography affording 5-bromo-1H-pyrazolo[3,4-b]pyridine x80 (yield: 2.1 percent; LC-MS (MH+): 198/200) and 6-bromopyrazolo[1 ,5-a]pyrimidine x81 (yield: 13.8 percent; LC-MS (MH+): 198/200).
Reference: [1] Patent: WO2006/128692, 2006, A2, . Location in patent: Page/Page column 86
  • 15
  • [ 2065-75-0 ]
  • [ 1225387-53-0 ]
  • [ 705263-10-1 ]
  • [ 875781-17-2 ]
YieldReaction ConditionsOperation in experiment
2.1% at 20℃; Heating / reflux A solution of 1 H-pyrazol-5-amine x79 (25 g, 1 eq, 0.3 mol) and bromomalonaldehyde x9 (45.4 g, 1 eq, 0.3 mol) ethanol (250 ml) is refluxed for 2 hours. After cooling, the reaction mixture is stirred at room temperature overnight. The solvent is removed under reduced pressure and the crude is purified using chiral chromatography affording 5-bromo-1H-pyrazolo[3,4-b]pyridine x80 (yield: 2.1 percent; LC-MS (MH+): 198/200) and 6-bromopyrazolo[1 ,5-a]pyrimidine x81 (yield: 13.8 percent; LC-MS (MH+): 198/200).
Reference: [1] Patent: WO2006/128692, 2006, A2, . Location in patent: Page/Page column 86
  • 16
  • [ 2065-75-0 ]
  • [ 1225387-53-0 ]
  • [ 875781-17-2 ]
YieldReaction ConditionsOperation in experiment
25% for 6 h; Heating; Reflux; Inert atmosphere of N2 lH-Pyrazol-5-amine (5.3 g, 64 mmol) and 2-bromomalonaldehyde(9.9 g, 64 mmol) were suspended in acetic acid (100 mL). The reaction mixture was heated <n="82"/>to reflux under N2 for 6 hours. The reaction mixture was cooled to room temperature and concentrated to give a solid. The crude solids were suspended in MeOH (200 mL) and absorbed onto silica gel (200 g). The crude product was purified by column chromatography, eluting with hexanes/ethyl acetate (4:1), hexanes/ethyl acetate (2:1) to give 5-bromo-lH- pyrazolo[3,4-b]pyridine as a solid (3.1 g, 25percent).
Reference: [1] Patent: WO2009/111279, 2009, A1, . Location in patent: Page/Page column 79-80
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