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[ CAS No. 1351401-26-7 ] {[proInfo.proName]}

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Chemical Structure| 1351401-26-7
Chemical Structure| 1351401-26-7
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CAS No. :1351401-26-7 MDL No. :MFCD30471207
Formula : C10H9FN2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W :208.19 Pubchem ID :-
Synonyms :

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Application In Synthesis of [ 1351401-26-7 ]

* 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.

  • Downstream synthetic route of [ 1351401-26-7 ]

[ 1351401-26-7 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 959615-64-6 ]
  • [ 540-51-2 ]
  • [ 1351401-26-7 ]
YieldReaction ConditionsOperation in experiment
75% With caesium carbonate In N,N-dimethyl-formamide at 120℃; for 4h; Sealed tube; 4.1.3 General procedure for synthesis of 7-fluoro-1-(2-hydroxyethyl)-1,5-naphthyridin-2(1H)-one (7) To a solution corresponding 7-fluoro-1,5-naphthyridin-2(1H)-one (6) (1g, 6.09 mmol) in dry N,N′-dimethyl formamide (10 mL) was added Cs2CO3 (4.95 g, 15.23 mmol) and followed by 2-bromoethanol (0.913 g, 7.31 mmol) and heated in sealed tube at 120°C for 4h (monitored by TLC & LCMS for completion). The reaction mixture was then filtered through celite and washed with dichloromethane. The filtrate was concentrated under reduced pressure. The reaction mixture was further extracted with ethyl acetate (3 × 40 mL). The combined organic extracts were washed with brine (2 × 40 mL) and water (3 × 50 mL), dried (MgSO4) and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography using hexane: ethyl acetate as eluent to give the corresponding 7-fluoro-1-(2-hydroxyethyl)-1,5-naphthyridin-2(1H)-one (7) (0.953 g, 75 %) as pale yellow solid. M.p: 241-243°C. 1H NMR [300MHz, DMSO-d6] δH: 8.14-6.52 (m, 4H), 3.74-3.47 (m, 5H). 13C NMR [DMSO-d6] δC: 162.3, 157.8, 147.5, 140.1, 132.3, 125.6, 123.2, 110.1, 64.5, 46.2. ESI-MS m/z 209 (M+H)+. Anal Calcd for C10H9FN2O2: C, 57.69; H, 4.36; N, 13.46; Found: C, 57.72; H, 4.38; N, 13.45.
75.6% With caesium carbonate In N,N-dimethyl-formamide for 4h; Sealed tube; General procedure for synthesis of 7-fluoro-1-(2-hydroxyethyl)-1,5-naphthyridin-2(1H)-one (2) To a solution of corresponding 7-fluoro-1,5-naphthyridin-2(1H)-one (1) (1 g, 6.09 mmol) (1 equiv) in dry N,N' dimethyl formamide (10 mL) was added Cs2CO3 (4.95 g, 15.23 mmol) (2.5 equiv) and followed by 2-bromoethanol (0.913 g, 7.31 mmol) (1.2 equiv) and heated in sealed tube at 120 °C for 4 h (monitored by TLC & LCMS for completion). The reaction mixture was then filtered through celite and washed with dichloromethane. The filtrate was concentrated under reduced pressure. The reaction mixture was further extracted with ethyl acetate (3 * 40 mL). The combined organic extracts were washed with brine (2 * 40 mL) and water (3 * 50 mL), dried (MgSO4) and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography using hexane (40%)/ethyl acetate (60%) as eluent to give the corresponding 7-fluoro-1-(2-hydroxyethyl)-1,5-naphthyridin-2(1H)-one (0.953 g, 75.6%) as pale yellow solid. 1H NMR [300 MHz, DMSO-d6] δH: 3.68 (t, J = 6 Hz, 2H, -CH2), 4.28 (t, J = 6 Hz, 2H, -CH2), 6.67 (d, J = 9.6 Hz, 1H, -C=CH), 7.51 (s, 1H, Ar-H), 7.86 (d, J = 9.6 Hz, 1H, -C=CH), 8.13 (s, 1H, -OH), 8.37 (d, J = 2.6 Hz, 1H, Ar-H). 13C NMR [DMSO-d6] δc: 162.3, 157.8, 147.5, 140.1, 132.3, 125.6, 123.2, 110.1, 64.5, 46.2. ESI-MS m/z (Calcd for C10H9FN2O2: 208.19); Found: 209.24 (M+H)+. Anal Calcd for C10H9FN2O2: C, 57.69; H, 4.36; N, 13.46; Found: C, 57.72; H, 4.38; N, 13.45.
71.7% Stage #1: 7-fluoro-1,5-naphthyridin-2(1H)-one With caesium carbonate In dimethyl sulfoxide at 20℃; for 0.166667h; Stage #2: 2-bromoethanol In dimethyl sulfoxide at 90℃;
71.7% Stage #1: 7-fluoro-1,5-naphthyridin-2(1H)-one With caesium carbonate In dimethyl sulfoxide at 20℃; for 0.166667h; Stage #2: 2-bromoethanol In dimethyl sulfoxide at 20 - 90℃;

Reference: [1]Bobesh, Karyakulam Andrews; Renuka, Janupally; Jeankumar, Variam Ullas; Shruti, Singh Kakan; Sridevi, Jonnalagadda Padma; Yogeeswari, Perumal; Sriram, Dharmarajan [European Journal of Medicinal Chemistry, 2014, vol. 85, p. 593 - 604]
[2]Bobesh, Karyakulam Andrews; Renuka, Janupally; Srilakshmi, Rudraraju Reshma; Yellanki, Swapna; Kulkarni, Pushkar; Yogeeswari, Perumal; Sriram, Dharmarajan [Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 1, p. 42 - 52]
[3]Hameed P, Shahul; Patil, Vikas; Solapure, Suresh; Sharma, Umender; Madhavapeddi, Prashanti; Raichurkar, Anandkumar; Chinnapattu, Murugan; Manjrekar, Praveena; Shanbhag, Gajanan; Puttur, Jayashree; Shinde, Vikas; Menasinakai, Sreenivasaiah; Rudrapatana, Suresh; Achar, Vijayashree; Awasthy, Disha; Nandishaiah, Radha; Humnabadkar, Vaishali; Ghosh, Anirban; Narayan, Chandan; Ramya; Kaur, Parvinder; Sharma, Sreevalli; Werngren, Jim; Hoffner, Sven; Panduga, Vijender; Kumar, C. N. Naveen; Reddy, Jitendar; Kumar Kn, Mahesh; Ganguly, Samit; Bharath, Sowmya; Bheemarao, Ugarkar; Mukherjee, Kakoli; Arora, Uma; Gaonkar, Sheshagiri; Coulson, Michelle; Waterson, David; Sambandamurthy, Vasan K.; De Sousa, Sunita M. [Journal of Medicinal Chemistry, 2014, vol. 57, # 11, p. 4889 - 4905]
[4]Hameed P, Shahul; Raichurkar, Anandkumar; Madhavapeddi, Prashanti; Menasinakai, Sreenivasaiah; Sharma, Sreevalli; Kaur, Parvinder; Nandishaiah, Radha; Panduga, Vijender; Reddy, Jitendar; Sambandamurthy, Vasan K.; Sriram [ACS Medicinal Chemistry Letters, 2014, vol. 5, # 7, p. 820 - 825]
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  • [ 884495-37-8 ]
  • [ 1351401-26-7 ]
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