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[ CAS No. 52023-68-4 ]

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Chemical Structure| 52023-68-4
Chemical Structure| 52023-68-4
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Product Details of [ 52023-68-4 ]

CAS No. :52023-68-4MDL No. :MFCD00119562
Formula : C9H13N3O Boiling Point : 414.4°C at 760 mmHg
Linear Structure Formula :-InChI Key :N/A
M.W :179.22Pubchem ID :104059
Synonyms :

Computed Properties of [ 52023-68-4 ]

TPSA : 51.4 H-Bond Acceptor Count : 4
XLogP3 : 0.3 H-Bond Donor Count : 1
SP3 : 0.44 Rotatable Bond Count : 1

Safety of [ 52023-68-4 ]

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

Application In Synthesis of [ 52023-68-4 ]

  • Upstream synthesis route of [ 52023-68-4 ]
  • Downstream synthetic route of [ 52023-68-4 ]

[ 52023-68-4 ] Synthesis Path-Upstream   1~6

  • 1
  • [ 26820-62-2 ]
  • [ 52023-68-4 ]
YieldReaction ConditionsOperation in experiment
100% With hydrogen In ethanol for 5 h; A mixture containing 1.65 g (7.8 mmol) of 4-(5-nitro-2-pyridinyl)morpholine, 160 mg of 5 percent Pt on carbon, and 20 ml. of EtOH was subjected to a 50 psi H2 atm for 5 h. The reaction mixture was filtered through a pad of Celite and the solvents were removed under reduced pressure to give 1.4 g (100percent) of 6-(4-morpholinyl)-3- pyridinamine as a purple solid: 1H NMR (400 MHz, DMSO-c/6) δ 7.60 (d, J = 2.9 Hz, 1 H), 6.92 (dd, J = 8.8 and 2.9 Hz, 1 H), 6.62 (d, J = 8.8 Hz, 1 H), 4.59 (brs, 2 H), 3.65 - 3.72 (m, 4 H), and 3.17 (dt, J = 4.9 and 2.4 Hz, 4 H).
100% With hydrogen In ethanol for 5 h; Step B: 6-(4-Morpholinyl)-3-pyridinamine; A mixture containing 1.65 g (7.8 mmol) of 4-(5-nitro-2-pyridinyl)morpholine, 160 mg of 5percent Pt on carbon, and 20 mLof EtOHI was subjected to a 50 psi H2 atmosphere for 5 h. The reaction mixture was filtered through a pad of Celite and the solvents were removed under reduced pressure to give 1.4 g (100percent) of 6-(4-morpholinyl)-3- pyridinamine as a purple solid: 1H-NMR (400 MHz, DMSO-Of6) δ 7.60 (d, J = 2.9 Hz, 1 H), 6.92 (dd, J =8.8 and 2.9 Hz, 1 H), 6.62 (d, J = 8.8 Hz, 1 H), 4.59 (brs, 2 H), 3.65 - 3.72 (m, 4 H), and 3.17 (dt, J =4.9 and 2.4 Hz, 4 H).
100% With hydrogen In ethanol at 20℃; for 5 h; A mixture containing 1 65 g (7 8 mmol) of 4-(5-nιtro-2-pyrιdιnyl)morpholιne, 160 mg of 5percent Pt on carbon, and 20 mL of EtOHI was subjected to a 50 psi H2 atmosphere for 5 h The reaction mixture was filtered through a pad of Celite and the solvents were removed under reduced pressure to give 1 4 g (100percent) of 6-(4-morpholιnyl)-3- pyridinamine as a purple solid 1H-NMR (400 MHz, DMSO-Cf6) δ 7 60 (d, J = 2 9 Hz, 1 H), 6 92 (dd, J =8 8 and 2 9 Hz, 1 H), 6 62 (d, J = 8 8 Hz, 1 H), 4 59 (brs, 2 H), 3 65 - 3 72 (m, 4 H), and 3 17 (dt, J =4 9 and 24 Hz, 4 H)
100% With hydrogen In methanol at 20℃; for 2.5 h; The mixture of Ib (300mg, 1.36mmol) and Pd/C (10percent, 300mg) in methanol was hydro genated at atmosphere at r.t. for 2.5h, filtered and concentrated to give Ic (258mg, 100percent).
99% With hydrogen; palladium In tetrahydrofuran at 20℃; To a solution of 4-(5-nitropyridin-2-yl) morpholine (3.89 g, 18.60 mmol) in THE (100 mL) was added catalyst Pd/C (0.5 g). The reaction was stirred at rt under H2 overnight, and filtered. The filtrate was concentrated in vacuo to give the title compound as a brown-red solid (3.30 g, 99percent).
99% With palladium on activated charcoal; hydrogen In tetrahydrofuran at 20℃; To a solution of 4-(5-nitropyridin-2-yl)morpholine (3.89 g, 18.60 mmol) in THF (100 mL) was added catalyst Pd/C (0.5 g).
The reaction was stirred at rt under H2 overnight, and filtered.
The filtrate was concentrated in vacuo to give the title compound as a brown-red solid (3.30 g, 99percent).
99% With palladium on activated charcoal; hydrogen In tetrahydrofuran at 20℃; In a 100 mL round bottom flask, 4-(5-nitropyridin-2-yl)morpholine (3.89 g, 18.60 mmol) was dissolved in THF (100 mL),After palladium/carbon (0.5 g) was added, H2 was bubbled in and stirred overnight at room temperature.After the mixture was filtered, the filtrate was collected and the solvent was evaporated under reduced pressure and dried in vacuo to give a red-brown solid (3.30 g, 99percent).
97% With palladium 10% on activated carbon; hydrogen In ethanol; ethyl acetate at 70℃; for 0.5 h; H-Cube.(TM). (General flow chemistry reduction method). Using 10percent Pd/C as catalyst, a solution of compound 3b (1 mmol, 208 mg) in a 1:1 mixture of ethyl acetate: ethanol (30 mL) was pumped though the H-Cube.(TM).. The pressure of the system was set to 1 bar, and the temperature to 70 °C. After 30 minutes, all the reaction mixture had passed though the HCube.(TM).. The fraction was analyzed using TLC, which showed complete conversion of the product, and the solvent was reduced to dryness, affording a dark red oil 171 mg (96percent) yield. The CatCart.(TM). was then washed with ethanol for approximately 10 minutes and the washings were discarded.
88% With hydrogen In ethanol at 20℃; for 2 h; Into a EtOH (250 mL) solution of 4-(5-nitropyridin-2-yl)morpholine (4.9 g, 23.4 mmol), 10percent Pd on activated carbon, 500 mg, was added. Hydrogenation was carried out in a Parr flask at room temperature, at 40 psi for 2 hr. The solids were filtered off and the filtrate was collected. The solvent was removed in vacuo. 6-Morpholinopyridin-3-amine, as a purple solid, was obtained: 3.7 g (88percent yield); 1H NMR (300 MHz, DMSO) δ 7.64 (d, J=2.7, 1H), 6.96 (dd, J=2.7, 8.8, 1H), 6.65 (d, J=8.8, 1H), 4.63 (s, 2H), 3.72-3.69 (m, 4H), 3.21-3.18 (m, 4H); LCMS (M+) m/z 180.08.
87% With palladium 10% on activated carbon; hydrogen In ethanol at 25℃; for 16 h; Under hydrogen (1 atm), to a solution of compound 62-b (2.0 g, 9.62 mmol) in ethanol (20 mL) was added 10percent Pd—C (0.2 g). The mixture was stirred at 25° C. for 16 hours, and then filtrated, the filtrate was concentrated under reduced pressure to give brown solid 62-a (1.5 g, yield: 87percent), which was used directly for the next step without purification. LC-MS (ESI): m/z=180 [M+H]+.
85% for 2 h; To a solution of the compound ha (2.50g, 11.9Smmol) in MeOH (5OmL) palladium 10percent on carbon (0.51 g) was added. The resulting mixture was stirred under hydrogen atmosphere for 2 hours. After completion of the reaction, the reaction mixture was filtered and the filtrate was concentrated to afford the compound lib (1.82g, 85percent).
84% With palladium on activated charcoal; hydrogen In methanol at 20℃; for 3 h; To a solution of 4-(5-nitropyridin-2-yl)morpholine (210 mg, 1 mmol) in methanol (15 mL) was added Pd/C (20 mg), and the mixture was hydrogenated at r.t under atmosphere pressure for 3 h. TLC showed that the reaction was complete. The resultant was filtered to remove Pd/C, and the filtrate was purified by silica gel column (PE/EtOAc, 1/1) to give 150 mg (yield: 84percent) of 6-morpholinopyridin-3-amine as a brown solid
79.3% With hydrogenchloride; iron In ethanol; water at 80℃; for 3 h; General procedure: To the solution of 14a-c, 14e-g, 15a-g, 16a-c or 17a-c (0.005mol) in ethanol/water (9:1, 30mL) was added hydrochloric acid (1.0mL) and iron powder (1.12g, 0.02mol). The resulting mixture was heated at 80°C for 3h, filtered through celite and concentrated to remove ethanol. The aqueous solution was extracted with ethyl acetate (3×100mL) and the combined organic layers were washed with water, brine, dried over Na2SO4 and concentrated to gain 18a-c, 18e-g, 19a-g, 20a-c or 21a-c
74% With palladium on activated charcoal; hydrazine hydrate In butan-1-ol at 120℃; for 6 h; Pd-C (5 mmol) catalyst was added to the solution ofcompound 2 (10 mmol) in butanol, and the mixture wasallowed to reflux in the presence of hydrazine hydrate (50mmol) for 6 hours. The progress of the reaction was monitoredby TLC. After completion of the reaction, the catalyst wasremoved by filtration, and the reaction solvent was removedunder reduced pressure. The obtained white solid wasrecrystallized from ethanol to afford the desired compound
70% With palladium on carbon; hydrogen In methanol at 20℃; for 12 h; General procedure: A mixture of 2-chloro-5-nitropyridine (3) (50mmol), morpholine (100mmol), and K2CO3 (100mmol) in THF (50mL) were stirred at 80°C for 4h. And then the mixture was concentrated to 20mL and poured into water (100mL), the yellow solid precipitation formed. After filtration, wash with purified water and dry, the desired compound 3a was obtained. 3b Was got with the same method. The mixture of 3a–3b (20mmol) and Pd/C (20percent, 500mg) in methanol was hydrogenated at atmosphere at r.t. for 12h, followed by filtration and concentration to afford compounds 4a–4b.

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[2] Patent: WO2009/76140, 2009, A1, . Location in patent: Page/Page column 237
[3] Patent: WO2010/104899, 2010, A1, . Location in patent: Page/Page column 106
[4] Patent: WO2009/154769, 2009, A1, . Location in patent: Page/Page column 35
[5] Patent: WO2014/12360, 2014, A1, . Location in patent: Paragraph 00355
[6] Patent: US2015/87639, 2015, A1, . Location in patent: Paragraph 0638
[7] Patent: TWI607995, 2017, B, . Location in patent: Page/Page column 144
[8] Journal of Medicinal Chemistry, 2018, vol. 61, # 9, p. 3855 - 3869
[9] Tetrahedron Letters, 2011, vol. 52, # 45, p. 5905 - 5909
[10] Patent: US2010/190770, 2010, A1, . Location in patent: Page/Page column 85
[11] Patent: US2015/336982, 2015, A1, . Location in patent: Paragraph 0391; 0393
[12] Patent: WO2018/19252, 2018, A1, . Location in patent: Page/Page column 39; 40
[13] Patent: WO2013/126608, 2013, A1, . Location in patent: Paragraph 00643
[14] Bioorganic Chemistry, 2018, vol. 81, p. 689 - 699
[15] RSC Advances, 2016, vol. 6, # 9, p. 6896 - 6904
[16] Revue Roumaine de Chimie, 2017, vol. 62, # 3, p. 199 - 205
[17] Molecules, 2012, vol. 17, # 4, p. 4703 - 4716
[18] Chinese Chemical Letters, 2016, vol. 27, # 1, p. 1 - 6
[19] Journal of the American Chemical Society, 1945, vol. 67, p. 536,537
[20] Patent: EP1389611, 2004, A1, . Location in patent: Page 6
[21] Patent: US6407120, 2002, B1, . Location in patent: Page column 34
[22] Patent: US2007/123504, 2007, A1, . Location in patent: Page/Page column 12
[23] ACS Medicinal Chemistry Letters, 2011, vol. 2, # 6, p. 481 - 484
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  • 2
  • [ 110-91-8 ]
  • [ 4548-45-2 ]
  • [ 52023-68-4 ]
YieldReaction ConditionsOperation in experiment
93%
Stage #1: With triethylamine In dichloromethane at 20℃; for 12 h;
Stage #2: With palladium on activated charcoal; hydrogen In ethanol for 2 h;
A mixture of 2-chloro-5-nitropyridine (303 mg, 1.91 mmol, 1.0 equiv), morpholine (0.5 mL,5.74 mmol, 3.0 equiv) and Et3N (483 mg, 0.67 mL, 2.5 equiv) in CH2Cl2 (4 mL) was stirred at roomtemperature overnight. The reaction mixture was diluted with water (10 mL) and extracted withCH2Cl2 (30 mL 3). The combined organic layers were washed with water (30 mL 6) and brine(1x30 mL), dried over anhydrous Na2SO4 and concentrated in vacuo to give a yellow solid. 70 mg ofthe yellow solid (0.335 mmol, 1.0 eq) were diluted in EtOH (5 mL) and a spatula tip of catalyst Pd/Cwas added. The obtained mixture was hydrogenated for 2 h, using a Hypem XP hydrogen generator(h2planet, Milan, Italy), Pressure was set at 1.5 bar. The crude mixture was filtered on Celite, and thefiltrate was evaporated to obtain a red solid. Yield: 93percent over two steps. TLC (hexane:ethyl acetate =4:6 v/v + Et3N): Rf = 0.15. 1H-NMR (CDCl3) δ 7.79 (d, J = 2.7 Hz, 1H), 7.01 (dd, J = 8.8, 2.7 Hz, 1H),6.73 (brs, 2H, NH2), 6.56 (d, J = 8.8 Hz, 1H), 3.82 (m, 4H), 3.33 (m, 4H). 13C-NMR (CDCl3) δ 154.02,135.09, 134.58, 126.42, 108.41, 66.80 (2C), 47.08 (2C). ESI()MS: m/z 178 [M-H]-.
Reference: [1] Molecules, 2018, vol. 23, # 8,
  • 3
  • [ 110-91-8 ]
  • [ 13534-97-9 ]
  • [ 52023-68-4 ]
Reference: [1] Organic Letters, 2017, vol. 19, # 11, p. 2809 - 2812
  • 4
  • [ 4548-45-2 ]
  • [ 52023-68-4 ]
Reference: [1] Molecules, 2012, vol. 17, # 4, p. 4703 - 4716
[2] Patent: WO2013/91502, 2013, A1,
[3] Patent: WO2013/126608, 2013, A1,
[4] Organic Process Research and Development, 2006, vol. 10, # 6, p. 1157 - 1166
[5] Patent: WO2014/12360, 2014, A1,
[6] Patent: US2014/329800, 2014, A1,
[7] Patent: US2015/87639, 2015, A1,
[8] Patent: TWI607995, 2017, B,
[9] Patent: WO2015/131080, 2015, A1,
[10] Patent: US2015/336982, 2015, A1,
[11] Chinese Chemical Letters, 2015, vol. 26, # 10, p. 1307 - 1310
[12] Chinese Chemical Letters, 2016, vol. 27, # 1, p. 1 - 6
[13] RSC Advances, 2016, vol. 6, # 9, p. 6896 - 6904
[14] European Journal of Medicinal Chemistry, 2017, vol. 125, p. 1036 - 1050
[15] Patent: WO2018/19252, 2018, A1,
[16] Bioorganic Chemistry, 2018, vol. 81, p. 689 - 699
[17] Patent: WO2009/154769, 2009, A1,
  • 5
  • [ 4487-59-6 ]
  • [ 52023-68-4 ]
Reference: [1] Tetrahedron Letters, 2011, vol. 52, # 45, p. 5905 - 5909
  • 6
  • [ 456-24-6 ]
  • [ 52023-68-4 ]
Reference: [1] Revue Roumaine de Chimie, 2017, vol. 62, # 3, p. 199 - 205
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