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[ CAS No. 5401-94-5 ]

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2D
Chemical Structure| 5401-94-5
Chemical Structure| 5401-94-5
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Product Details of [ 5401-94-5 ]

CAS No. :5401-94-5MDL No. :MFCD00005693
Formula : C7H5N3O2 Boiling Point : 383.3°C at 760 mmHg
Linear Structure Formula :-InChI Key :-
M.W :163.13Pubchem ID :21501
Synonyms :

Computed Properties of [ 5401-94-5 ]

TPSA : 74.5 H-Bond Acceptor Count : 3
XLogP3 : - H-Bond Donor Count : 1
SP3 : 0.00 Rotatable Bond Count : 0

Safety of [ 5401-94-5 ]

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 [ 5401-94-5 ]

  • Upstream synthesis route of [ 5401-94-5 ]
  • Downstream synthetic route of [ 5401-94-5 ]

[ 5401-94-5 ] Synthesis Path-Upstream   1~14

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Reference: [1] Journal of the Chemical Society, 1955, p. 2412,2419
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YieldReaction ConditionsOperation in experiment
100% With hydrogen In tetrahydrofuran at 25℃; Autoclave; Inert atmosphere Preparation 4
1H-indazol-5-amine
To a 5000 mL autolcave equipped with a H2 inlet, a thermometer, and a mechanical stirrer is added a solution of 5-nitro-1H-indazole (500 g, 3.06 mol) in tetrahydrofuran (THF, 3500 mL), followed by palladium on carbon (10percent, 50 g, 141 mmol).
The resulting mixture is stirred overnight at 25° C. under H2 atmosphere (5 kg pressure).
After it is purged with N2, the mixture is filtered, and the filtrate is concentrated under vacuum to give the title compound (420 g, 100percent) as a brown solid. MS (m/z): 134.1 (M+H).
97% With hydrogen In methanol A mixture of 5-nitro-1H-indazole (25 g, 0.153 mmol, commercially available) and 10percent Pd/C (2.0 g) in MeOH was stirred under H2 (1 atm) overnight. After filtration, the filtrate was concentrated to yield 20 g (97percent) of 1H-indazol-5-amine as a yellow solid.
97% With hydrogen In methanol Example B16
A mixture of 5-nitro-1H-indazole (50 g, 0.31 mol) and 10percent Pd/C (5.0 g) in MeOH (400 mL) was heated under H2 (30 psi) atmosphere overnight.
After the mixture was filtered, the filtrate was concentrated to give 1H-indazol-5-ylamine as a yellow solid (40g, 97percent yield).
1H NMR (300 MHz, DMSO-d6) δ 12.50 (br s, 1H), 7.70 (s, 1H), 7.22 (d, J=6.6 Hz, 1H), 6.77 (d, J=6.6 Hz, 1H), 6.74 (s, 1H), 4.72 (br s, 1 H); MS (ESI) m/z: 134.2 (M+H+).
97% With palladium 10% on activated carbon; hydrogen In methanol A mixture of 5-nitro-lH-indazole (50 g, 0.31 mol) and 10 percent Pd/C (5.0 g) in MeOH (400 mL) was heated under H2 (30 psi) atmosphere overnight. After the mixture was filtered, the filtrate was concentrated to give lH-indazol-5-ylamine as a yellow solid (40 g, 97percent yield). 1H NMR (300 MHz, DMSO-i/6) δ 12.50 (br s, 1 H), 7.70 (s, 1 H), 7.22 (d, J= 6.6 Hz, 1 H), 6.77 (d, J= 6.6 Hz, 1 H), 6.74 (s, 1 H), 4.72 (br s, 1 H); MS (ESI) m z: 134.2 (M+H+).

Reference: [1] Patent: US2012/28984, 2012, A1, . Location in patent: Page/Page column 3
[2] Patent: WO2006/71940, 2006, A2, . Location in patent: Page/Page column 409
[3] Patent: US2008/90856, 2008, A1, . Location in patent: Page/Page column 45
[4] Patent: WO2013/36232, 2013, A2, . Location in patent: Paragraph 00321
[5] MedChemComm, 2016, vol. 7, # 5, p. 881 - 899
[6] Bioorganic Chemistry, 2019, vol. 82, p. 340 - 359
[7] Tetrahedron, 2008, vol. 64, # 28, p. 6711 - 6723
[8] Organic Letters, 2016, vol. 18, # 11, p. 2774 - 2776
[9] Tetrahedron Letters, 2017, vol. 58, # 49, p. 4632 - 4637
[10] Chemische Berichte, 1922, vol. 55, p. 1141,1157
[11] Justus Liebigs Annalen der Chemie, 1927, vol. 454, p. 306
[12] Journal of the Chemical Society, 1955, p. 2412,2419
[13] Bioorganic and Medicinal Chemistry Letters, 1999, vol. 9, # 7, p. 925 - 930
[14] Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy, 2014, vol. 132, p. 733 - 742
[15] Patent: WO2016/57834, 2016, A1, . Location in patent: Paragraph 000325
[16] Bioorganic and Medicinal Chemistry, 2018, vol. 26, # 9, p. 2372 - 2380
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Reference: [1] Patent: US2003/153596, 2003, A1,
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Reference: [1] Journal of Medicinal Chemistry, 2005, vol. 48, # 4, p. 1107 - 1131
[2] Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 11, p. 1401 - 1405
[3] Chinese Chemical Letters, 2011, vol. 22, # 11, p. 1277 - 1280
[4] European Journal of Medicinal Chemistry, 2018, vol. 155, p. 316 - 336
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YieldReaction ConditionsOperation in experiment
44% With potassium carbonate In acetonitrile at 70℃; To a solution of 5-nitroindazole (10.0 g, 61.3 MMOL) in acetonitrile (100 mL) was added potassium carbonate (16.9 g, 122.6 MMOL) and benzyl bromide (13.6 g, 79.7 MMOL). The resulting yellow reaction mixture was heated with stirring at 70°C overnight. Upon cooling down, the solid was filtered off and washed with methylene chloride. The filtrate was concentrated to dryness and the resulting residue was purified by flash chromatography eluting with 17-25percent ethyl acetate in hexanes (v/v) yielding 7.0 g (44percent) of the corresponding 1-Benzyl-5-nitro-1 H-indazole as a yellow solid. 7.61g (136 MMOL, 5 equiv) of Iron powder (4.03 g, 72.1 MMOL) was added slowly to the solution of 1-BENZYL-5-NITRO-1 H-INDAZOLE (6. 9 g, 27.2 MMOL) in acetic acid (200 mL). After stirring at room temperature overnight, the reaction mixture became milky with formation of a white precipitate. The precipitate was filtered off and the filtrate was concentrated to ca. 20 mL. The residue was diluted with water (200 mL) and neutralized by slow addition of sodium hydroxide. The mixture was then extracted with ethyl acetate (500x5 mL). The organic layer were combined, dried over sodium sulfate, filtered and concentrated to dryness to afford 1-BENZYL-1 H-INDAZOL-5-YLAMINE (5.23 g, 82percent) as a brown SOLID. H NMR (DMSO-D6) : 8 7.72 (s, 1H), 7.35 (d, J=8.8 Hz, 1H), 7.24-7. 14 (m, 5H), 6.74 (m, 2H), 5.49 (s, 2H), 4.80 (br, 2H). ES-LCMS: RT = 0.93 min; [M+H] + = 224.2.
Reference: [1] Patent: WO2005/10008, 2005, A1, . Location in patent: Page/Page column 117-118
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Reference: [1] Journal of Medicinal Chemistry, 2005, vol. 48, # 4, p. 1107 - 1131
[2] Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 11, p. 1401 - 1405
[3] Patent: US9199973, 2015, B2, . Location in patent: Page/Page column 39
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Reference: [1] Patent: US2003/139416, 2003, A1,
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Reference: [1] European Journal of Medicinal Chemistry, 2018, vol. 155, p. 316 - 336
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  • [ 100-44-7 ]
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  • [ 23856-20-4 ]
Reference: [1] Chinese Chemical Letters, 2011, vol. 22, # 11, p. 1277 - 1280
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Reference: [1] Journal of Medicinal Chemistry, 2003, vol. 46, # 26, p. 5663 - 5673
[2] Journal of Chemical Research, Miniprint, 1990, # 11, p. 2601 - 2615
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YieldReaction ConditionsOperation in experiment
100% With hydrogen In ethanol for 23 h; A suspension of 10percent Pd-C (0.054 g, 0.051 mmol in Pd) and the above carbamate Example 105 (2.647 g, 10.1 mmol) in 95percent EtOH was degassed under reduced pressure then reacted under hydrogen. After 23 h the solvent was evaporated on a rotary evaporator. EtOAc (20 mL) was added and the reaction filtered then slowly EPO <DP n="125"/>concentrated on a rotary evaporator yielding 2.335 g (100percent) of a tan solid.LC- MS (ESI) m/z 134 [M-Boc+H]+.
Reference: [1] Patent: WO2006/135383, 2006, A2, . Location in patent: Page/Page column 123-124
[2] Patent: WO2012/146724, 2012, A2,
[3] Patent: US2014/57942, 2014, A1,
[4] Patent: WO2014/68035, 2014, A1,
[5] Asian Journal of Chemistry, 2014, vol. 26, # 22, p. 7539 - 7543
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YieldReaction ConditionsOperation in experiment
96%
Stage #1: With dmap; triethylamine In dichloromethane for 17 h;
Stage #2: With citric acid; sodium chloride In dichloromethane; water
A soln of di-tert-butyl dicarbonate (6.719 g, 30.8 mmol) in DCM (20 mL) was added over 5 min to a suspension of 5-nitro-lH-indazole (5.009 g, 30.7 mmol), Et3N (4.30 mL, 30.9 mmol) and DMAP (0.751 g, 6.15 mmol) in DCM (60 mL). After 17 h the solution was washed with water (1 x 50 mL), 1 M citric acid (3 x 10 mL) and satd NaCl (1 x 20 mL), then dried (MgSO4), filtered through silica, washed with DCM and concentrated to give 7.75 g (96percent) an off-white solid. LC-MS (ESI) m/z 162 [M- Boc-H]-.
Reference: [1] Patent: WO2006/135383, 2006, A2, . Location in patent: Page/Page column 123
[2] Patent: WO2016/57834, 2016, A1,
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Reference: [1] Patent: US2012/28984, 2012, A1,
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Reference: [1] Patent: US2012/28984, 2012, A1,
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