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[ CAS No. 5228-49-9 ]

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2D
Chemical Structure| 5228-49-9
Chemical Structure| 5228-49-9
Structure of 5228-49-9 *Storage: {[proInfo.prStorage]}

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Product Details of [ 5228-49-9 ]

CAS No. :5228-49-9MDL No. :MFCD01318163
Formula : C8H7N3O2 Boiling Point : 332.9°C at 760 mmHg
Linear Structure Formula :-InChI Key :-
M.W :177.16Pubchem ID :280211
Synonyms :

Computed Properties of [ 5228-49-9 ]

TPSA : 63.6 H-Bond Acceptor Count : 3
XLogP3 : - H-Bond Donor Count : 0
SP3 : 0.13 Rotatable Bond Count : 0

Safety of [ 5228-49-9 ]

Signal Word:WarningClass:N/A
Precautionary Statements:P261-P305+P351+P338UN#:N/A
Hazard Statements:H302-H315-H319-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 5228-49-9 ]

  • Upstream synthesis route of [ 5228-49-9 ]
  • Downstream synthetic route of [ 5228-49-9 ]

[ 5228-49-9 ] Synthesis Path-Upstream   1~14

  • 1
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  • [ 50593-24-3 ]
YieldReaction ConditionsOperation in experiment
99% With iron; ammonium chloride In ethanol; water at 80℃; for 1 h; Step 2: Preparation of l-methyl-lH-indazol-5-amine Iron powder (5.04 g, 0.0903 mol) is added portionwise to a solution of l-methyl-5- nitro-lH-indazole (4.00 g, 0.0226 mol) and ammonium chloride (12.1 g, 0.225 mol) in ethanol (225 mL) and water (100 mL) at 8O0C. The mixture is stirred and heated for Ih, diluted with dichloromethane (500 mL) and filtered. The organic layer is separated, dried (Mg2SO4) and evaporated to afford the title compound (3.29 g, 99percent); HPLC (SYMMETRY C18 3.5 μM, 4.6 x 30 mm column; gradient elution 2percent-98percent MeCN with 0.1percent TFA over 10 min; 2 mL/min rate): retention time = 1.06 min; MS for C1OHnN3 m/z 147.2(M+H)+.
71% With hydrogenchloride; iron In ethanol; waterReflux Iron (3.62 g, 64.7 mmol) and concentrated hydrochloric acid (0.1 mL) were added to ethanol/water (20 mL/20 mL), and refluxed for 1 hour. The mixed reaction solution was added with l-methyl-5-nitro-lH-indazole (2.29 g, 12.9 mmol) obtained in above, and further refluxed for 3 hours or more. The reaction mixture was filtered through a Celite pad under reduced pressure, and washed with chloroform/2-propanol = 4/l(v/v). The filtrate obtained was distilled under reduced pressure, and dissolved in chloroform/2-propanol = 4/1 (v/v). The organic layer was washed with an aqueous solution of sodium bicarbonate and brine. The obtained organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to obtain the title compound (1.35 g, 71percent). -NMR Spectrum (300 MHz, OMSO-d6): δ 7.65 (d, 1H), 7.31 (d, 1H), 6.80 (d, 1H), 6.71 (d, 1H), 4.78 (s, 2H), 3.89 (s, 3H) MS(ESI+, m/z): 148 [M+H]+
71% With hydrogenchloride; iron In ethanol; waterReflux Iron (3.62 g, 64.7 mmol) and concentrated hydrochloric acid (0.1 mL) were added to ethanol/water (20 mL/20 mL), and refluxed for 1 hour. The mixed reaction solution was added with 1-methyl-5-nitro-1H-indazole (2.29 g, 12.9 mmol) obtained in <Step 1> above, and further refluxed for 3 hours or more. The reaction mixture was filtered through a Celite pad under reduced pressure, and washed with chloroform/2-propanol=4/1(v/v). The filtrate obtained was distilled under reduced pressure, and dissolved in chloroform/2-propanol=4/1 (v/v). The organic layer was washed with an aqueous solution of sodium bicarbonate and brine. The obtained organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to obtain the title compound (1.35 g, 71percent). 1H-NMR Spectrum (300 MHz, DMSO-d6): δ 7.65 (d, 1H), 7.31 (d, 1H), 6.80 (d, 1H), 6.71 (d, 1H), 4.78 (s, 2H), 3.89 (s, 3H) MS (ESI+, m/z): 148 [M+H]+
18% With ammonium chloride; acetic acid; zinc In ethanol; water; ethyl acetate at 20℃; for 1 h; Zinc powder (194 mmol), ammonium chloride (388 mmol), and acetic acid (33.3 mmol) were added, successively, to a solution of l-methyl-5-nitro-1H-indazole (19.1 mmol) in ethanol (50 mL), water (20 mL), and ethyl acetate (5 mL) and the resulting suspension was maintained at rt for 1 h. The insoluble solids were removed by filtration and the filtrate was concentrated. The residue was purified by Flash chromatography (5/1 petroleum ether/ethyl acetate) to provide 1 -methyl- 1H-indazol-5-amine in 18percent yield as a brown solid.
18% With ammonium chloride; acetic acid; zinc In ethanol; water; ethyl acetate at 20℃; for 1 h; 2. Synthesis of 1 -methyl- lH-indazol-5-amine.Zinc powder (194 mmol), ammonium chloride (388 mmol), and acetic acid (33.3 mmol) were added, successively, to a solution of l-methyl-5-nitro-lH-indazole (19.1 mmol) in ethanol (50 mL), water (20 mL), and ethyl acetate (5 mL) and the resulting suspension was maintained at rt for 1 h. The insoluble solids were removed by filtration and the filtrate was concentrated. The residue was purified by Flash chromatography (5/1 petroleum ether/ethyl acetate) to provide 1- methyl-lH-indazol-5-amine in 18percent yield as a brown solid.
18% With ammonium chloride; acetic acid; zinc In ethanol; water; ethyl acetate at 20℃; for 1 h; 2. Synthesis of l-methyl-lH-indazol-5-amine.Zinc powder (194 mmol), ammonium chloride (388 mmol), and acetic acid (33.3 mmol) were added, successively, to a solution of l-methyl-5-nitro-lH-indazole (19.1 mmol) in ethanol (50 mL), water (20 mL), and ethyl acetate (5 mL) and the resulting suspension was maintained at rt for 1 h. The insoluble solids were removed by filtration and the filtrate was concentrated. The residue was purified by Flash chromatography (5/1 petroleum ether/ethyl acetate) to provide 1- methyl-lH-indazol-5-amine in 18percent yield as a brown solid.

Reference: [1] Patent: WO2007/88478, 2007, A1, . Location in patent: Page/Page column 19
[2] Tetrahedron, 2008, vol. 64, # 28, p. 6711 - 6723
[3] Journal of Chemical Research, Miniprint, 1990, # 11, p. 2601 - 2615
[4] Patent: WO2013/100632, 2013, A1, . Location in patent: Page/Page column 95
[5] Patent: US2014/371219, 2014, A1, . Location in patent: Paragraph 0662; 0663; 0664
[6] Heterocycles, 2006, vol. 68, # 12, p. 2595 - 2605
[7] Patent: WO2009/23844, 2009, A2, . Location in patent: Page/Page column 132
[8] Patent: WO2010/21797, 2010, A1, . Location in patent: Page/Page column 97
[9] Patent: WO2010/24980, 2010, A1, . Location in patent: Page/Page column 115
[10] Justus Liebigs Annalen der Chemie, 1927, vol. 454, p. 306
[11] Patent: WO2016/57834, 2016, A1, . Location in patent: Paragraph 000407
[12] Patent: WO2004/108663, 2004, A1, . Location in patent: Page 106-107
  • 2
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  • [ 50593-24-3 ]
Reference: [1] Synthetic Communications, 2015, vol. 45, # 17, p. 2005 - 2013
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  • [ 50593-24-3 ]
Reference: [1] Heterocycles, 2006, vol. 68, # 12, p. 2595 - 2605
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  • [ 5401-94-5 ]
  • [ 74-88-4 ]
  • [ 5228-48-8 ]
  • [ 5228-49-9 ]
YieldReaction ConditionsOperation in experiment
58%
Stage #1: With caesium carbonate In tetrahydrofuran at 0℃; for 0.25 h;
Stage #2: at 0℃;
General procedure: Cesium carbonate (12.26mmol) was added to a solution of 5-nitroindazole 1 (6.13 mmol) in tetrahydrofuran (THF;25mL)cooledat 0°C. After 15 mn at 0°C, MeI or allyl bromide(6.13mmol) was added dropwise. Upon disappearance of the starting materialas indicated by TLC,the resulting mixture was evaporated.The crude material was dissolved with EtOAc(50mL),washed with water and brine,and dried over MgSO4; and the solvent was removed in vacuo.The resulting residue was purified by column chromatography on silica gel using EtOAc=hexane(3:7) to afford the desired products,1-alkyl-5-nitroindazole followed by2-alkyl-5-nitroindazole.
42%
Stage #1: With sodium hydride In tetrahydrofuran at 0℃;
Stage #2: at 0 - 20℃; for 3 h;
NaH (1.47 g, 36.8 mmol) was added to THF (40 mL) at 0° C. Separately, 5-nitroindazole (5.0 g, 30.6 mmol) was dissolved in THF (30 mL), and the mixed solution was slowly added to the prepared solution. Iodomethane (2.1 mL, 33.7 mmol) was added to the reaction solution at the same temperature, followed by stirring for 3 hours at room temperature. The reaction solution was concentrated under reduced pressure, and added with water and ethyl acetate. The reaction mixture was added with distilled water for quenching, diluted with ethyl acetate, and washed with distilled water. The organic layer was dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The concentrated compound (1-methyl added (Rf=0.3), 2-methyl added (Rf=0.1)) was purified using silica gel chromatography (ethyl acetate:hexane=1:1 (v/v)) to obtain the title compound (Rf=0.3, 2.29 g, 42percent). 1H-NMR Spectrum (300 MHz, DMSO-d6): δ 8.74 (d, 1H), 8.31 (dd, 1H), 8.20 (s, 1H), 7.47 (d, 1H), 4.15 (s, 3H) MS (ESI+, m/z): 178 [M+H]+
Reference: [1] Synthetic Communications, 2015, vol. 45, # 17, p. 2005 - 2013
[2] Tetrahedron, 2008, vol. 64, # 28, p. 6711 - 6723
[3] Patent: US2014/371219, 2014, A1, . Location in patent: Paragraph 0659; 0660; 0661
[4] Patent: WO2016/57834, 2016, A1, . Location in patent: Paragraph 000406
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  • [ 5228-48-8 ]
  • [ 5228-49-9 ]
Reference: [1] Heterocycles, 2006, vol. 68, # 12, p. 2595 - 2605
[2] Journal of Chemical Research, Miniprint, 1990, # 11, p. 2601 - 2615
[3] Justus Liebigs Annalen der Chemie, 1927, vol. 454, p. 306
  • 6
  • [ 5401-94-5 ]
  • [ 74-88-4 ]
  • [ 5228-48-8 ]
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YieldReaction ConditionsOperation in experiment
58%
Stage #1: With caesium carbonate In tetrahydrofuran at 0℃; for 0.25 h;
Stage #2: at 0℃;
General procedure: Cesium carbonate (12.26mmol) was added to a solution of 5-nitroindazole 1 (6.13 mmol) in tetrahydrofuran (THF;25mL)cooledat 0°C. After 15 mn at 0°C, MeI or allyl bromide(6.13mmol) was added dropwise. Upon disappearance of the starting materialas indicated by TLC,the resulting mixture was evaporated.The crude material was dissolved with EtOAc(50mL),washed with water and brine,and dried over MgSO4; and the solvent was removed in vacuo.The resulting residue was purified by column chromatography on silica gel using EtOAc=hexane(3:7) to afford the desired products,1-alkyl-5-nitroindazole followed by2-alkyl-5-nitroindazole.
42%
Stage #1: With sodium hydride In tetrahydrofuran at 0℃;
Stage #2: at 0 - 20℃; for 3 h;
NaH (1.47 g, 36.8 mmol) was added to THF (40 mL) at 0° C. Separately, 5-nitroindazole (5.0 g, 30.6 mmol) was dissolved in THF (30 mL), and the mixed solution was slowly added to the prepared solution. Iodomethane (2.1 mL, 33.7 mmol) was added to the reaction solution at the same temperature, followed by stirring for 3 hours at room temperature. The reaction solution was concentrated under reduced pressure, and added with water and ethyl acetate. The reaction mixture was added with distilled water for quenching, diluted with ethyl acetate, and washed with distilled water. The organic layer was dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The concentrated compound (1-methyl added (Rf=0.3), 2-methyl added (Rf=0.1)) was purified using silica gel chromatography (ethyl acetate:hexane=1:1 (v/v)) to obtain the title compound (Rf=0.3, 2.29 g, 42percent). 1H-NMR Spectrum (300 MHz, DMSO-d6): δ 8.74 (d, 1H), 8.31 (dd, 1H), 8.20 (s, 1H), 7.47 (d, 1H), 4.15 (s, 3H) MS (ESI+, m/z): 178 [M+H]+
Reference: [1] Synthetic Communications, 2015, vol. 45, # 17, p. 2005 - 2013
[2] Tetrahedron, 2008, vol. 64, # 28, p. 6711 - 6723
[3] Patent: US2014/371219, 2014, A1, . Location in patent: Paragraph 0659; 0660; 0661
[4] Patent: WO2016/57834, 2016, A1, . Location in patent: Paragraph 000406
  • 7
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  • [ 74-88-4 ]
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YieldReaction ConditionsOperation in experiment
83%
Stage #1: With sodium hydride In N,N-dimethyl-formamide at 0℃; for 1 h;
Stage #2: at 0 - 20℃; for 18 h;
Sodium hydride (55.0 mmol) was added to a solution of 5-nitro-1H-indazole (18.40 mmol) inN,N-dimethylformamide (50 mL) and the mixture was maintained for 60 min at 0 °C. To the mixture was added Methyl iodide (22.12 mmol) was added and the reaction mixture was allowed to warm to rt and was maintained for 18 h. The reaction mixture was quenched with water (60 mL), filtered through Celite, and the filtrate was concentrated to provide l-methyl-5-nitro-1H-indazole in 83percent yield as a yellow solid.
83%
Stage #1: With sodium hydride In N,N-dimethyl-formamide at 0℃; for 1 h;
Stage #2: at 0 - 20℃;
Intermediate 40: Synthesis of l-methyl-lH-indazole-5-sulfonyl chloride.1. Synthesis of 1 -methγl-5-nitro- lH-indazole.Sodium hydride (55.0 mmol) was added to a solution of 5-nitro-lH-indazole (18.40 mmol) in N.jV-dimethylformamide (50 mL) and the mixture was maintained for 60 min at 0 0C. To the mixture was added Methyl iodide (22.12 mmol) was added and the reaction mixture was allowed to warm to rt and was maintained for 18 h. The reaction mixture was quenched with water (60 mL), filtered through Celite, and the filtrate was concentrated to provide l-methyl-5- nitro-1/f-indazole in 83percent yield as a yellow solid.
83%
Stage #1: With sodium hydride In N,N-dimethyl-formamide at 0℃; for 1 h;
Stage #2: at 20℃; for 18 h;
Intermediate 40: Synthesis of l-methyl-l//-indazole-5-sulfonyl chloride. 1. Synthesis of l-methyl-5-nitro-lH-indazole.Sodium hydride (55.0 mmol) was added to a solution of 5-nitro-lH-indazole (18.40 mmol) in N,N-dimethylformamide (50 mL) and the mixture was maintained for 60 min at 0 0C. To the mixture was added Methyl iodide (22.12 mmol) was added and the reaction mixture was allowed to warm to rt and was maintained for 18 h. The reaction mixture was quenched with water (60 mL), filtered through Celite, and the filtrate was concentrated to provide l-methyl-5- nitro-l//-indazole in 83percent yield as a yellow solid.
55%
Stage #1: With sodium hydride In N,N-dimethyl-formamide at 20℃; for 0.5 h;
Stage #2: at 20℃;
Step 1: Preparation of l-methyl-5-nitro-lH-indazoleSodium hydride (5.40 g, 0.135 mol) is added portionwise to a solution of 5- nitroindazole (20.0 g, 0.122 mol) in DMF (250 mL) at room temperature. The reaction is <n="20"/>stirred for 30 minutes, iodomethane (8.40 mL, 0.135 mol) added dropwise, and the mixture allowed to react overnight at room temperature. The solvent is then removed in vacuo and the residue diluted with ethyl acetate, washed with water and brine, the organic layer dried (Mg2SO4) and evaporated. The residue is purified by flash chromatography (20percent EtOAc/Hexanes) to give the title compound (12.0 g, 55percent); HPLC (SYMMETRY C18 3.5 μM, 4.6 x 30 mm column; gradient elution 2percent-98percent MeCN with 0.1percent TFA over 10 min; 2 mL/min rate): retention time = 4.29 min; MS for C8H7N3O2 m/z 178.2(M+H)+.
42% With sodium hydride In tetrahydrofuran at 0 - 20℃; for 3 h; NaH (1.47 g, 36.8 mmol) was added to THF (40 mL) at 0°C. Separately, 5- nitroindazole (5.0 g, 30.6 mmol) was dissolved in THF (30 mL), and the mixed solution was slowly added to the prepared solution. Iodomethane (2.1 mL, 33.7 mmol) was added to the reaction solution at the same temperature, followed by stirring for 3 hours at room temperature. The reaction solution was concentrated under reduced pressure, and added with water and ethyl acetate. The reaction mixture was added with distilled water for quenching, diluted with ethyl acetate, and washed with distilled water. The organic layer was dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The concentrated compound (1 -methyl added (Rf = 0.3), 2-methyl added (Rf = 0.1)) was purified using silica gel chromatography (ethyl acetate:hexane = 1 : 1 (v/v)) to obtain the title compound (Rf = 0.3, 2.29 g, 42percent). -NMR Spectrum (300 MHz, DMSO- ): δ 8.74 (d, 1H), 8.31 (dd, 1H), 8.20 (s, 1H), 7.47 (d, 1H), 4.15 (s, 3H) MS(ESI+, m/z): 178 [M+H]+

Reference: [1] Patent: WO2009/23844, 2009, A2, . Location in patent: Page/Page column 132
[2] Patent: WO2010/21797, 2010, A1, . Location in patent: Page/Page column 97
[3] Patent: WO2010/24980, 2010, A1, . Location in patent: Page/Page column 114; 115
[4] Journal of Organic Chemistry, 2014, vol. 79, # 16, p. 7286 - 7293
[5] Patent: WO2007/88478, 2007, A1, . Location in patent: Page/Page column 18-19
[6] Patent: WO2013/100632, 2013, A1, . Location in patent: Page/Page column 94; 95
[7] Journal of Chemical Research, 2014, vol. 38, # 4, p. 202 - 207
[8] Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy, 2015, vol. 136, # PC, p. 1484 - 1490
[9] Journal of Molecular Structure, 2016, vol. 1119, p. 151 - 156
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  • [ 6850-23-3 ]
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YieldReaction ConditionsOperation in experiment
59% With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 1 h; General procedure: Procedure E: NaH (1.1 equiv) was added to the solution of amine (1 equiv) in anhydrous N,N-dimethylformamide. Iodomethane (1.1 equiv) was added dropwise to the reaction mixture at 0°C.The reaction was continued at room temperature until the starting material was consumed. The resulting mixture was diluted with ethyl acetate and washed with water and brine. The organic layer was dried over MgSO4 and concentrated under reduced pressure.The product was carried on to the next reaction without further purification or was isolated by column chromatography.
Reference: [1] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 13, p. 3821 - 3830
  • 9
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YieldReaction ConditionsOperation in experiment
83% With tert.-butylnitrite In tetrahydrofuran for 1 h; Reflux General procedure: A mixture of 3-amino-1-methyl-1H-indazole 2 (3.0 mmol) and tert-butyl nitrite (1.0 mL, 8.1 mmol, 2.7 equiv) in THF (12.0 mL) was heated to reflux for 1 h. The mixture was cooled to rt and then concentrated. H2O (10.0 mL) and EtOAc (20.0 mL) were added to the residue. The organic layer was washed with H2O (10.0 mL), brine (10.0 mL), dried over Na2SO4, filtered, and concentrated in vacuo. The residue was subjected to silica-gel chromatography by using Et2O/hexanes (1:4) as eluent to give the product 3.#10;
Reference: [1] Tetrahedron, 2013, vol. 69, # 19, p. 3907 - 3912
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Reference: [1] Russian Journal of General Chemistry, 2018, vol. 88, # 3, p. 425 - 429[2] Zh. Obshch. Khim., 2018, vol. 88, # 3, p. 397 - 401,5
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  • [ 5228-49-9 ]
Reference: [1] Heterocycles, 2006, vol. 68, # 12, p. 2595 - 2605
[2] Journal of Chemical Research, Miniprint, 1990, # 11, p. 2601 - 2615
[3] Justus Liebigs Annalen der Chemie, 1927, vol. 454, p. 306
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  • [ 5228-49-9 ]
Reference: [1] Tetrahedron, 2013, vol. 69, # 19, p. 3907 - 3912
  • 13
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  • [ 73105-48-3 ]
Reference: [1] Tetrahedron, 1980, vol. 36, p. 3523 - 3534
  • 14
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  • [ 756839-14-2 ]
Reference: [1] Patent: WO2004/108663, 2004, A1,
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