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Product Details of [ 959615-64-6 ]

CAS No. :959615-64-6 MDL No. :MFCD18836778
Formula : C8H5FN2O Boiling Point : -
Linear Structure Formula :- InChI Key :UHBAZQRMLAHIPL-UHFFFAOYSA-N
M.W :164.14 Pubchem ID :46900801
Synonyms :

Safety of [ 959615-64-6 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338 UN#:
Hazard Statements:H302-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 959615-64-6 ]

* 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 [ 959615-64-6 ]

[ 959615-64-6 ] Synthesis Path-Downstream   1~52

  • 1
  • [ 1003944-32-8 ]
  • [ 959615-64-6 ]
YieldReaction ConditionsOperation in experiment
86% Stage #1: 7-fluoro-2-methoxy-1,5-naphthyridine With hydrogen bromide; acetic acid at 20℃; for 18h; Stage #2: With water; sodium hydrogencarbonate at 20℃; for 1h; 7.b (b) .7-Fluoro- 1 , 5 -naphthyridin-2( 1 H)-one; A suspension of 7-fluoro-2-(methoxy)-l,5-naphthyridine (3.044g, 17.101mmol) in glacial acetic acid (50ml) at rt under argon, was treated with 33% HBr in acetic acid (50ml). After stirring at rt for 18 h, the solvents were evaporated (copious fumes of HBr were produced). The residue was treated with acetic acid (100ml) and re-evaporated, then stirred with water (200ml) and the pH of the suspension was adjusted to pH 4 by addition of solid sodium hydrogen carbonate. The mixture was then stirred at rt for 1 hour then the solid was isolated by filtration with suction to give an off-white damp solid. The product was dried on the sinter with suction for 2 hours then dried in a vacuum desiccator over P2O5 overnight to give the desired compound as a white solid (2.412g, 86%). MS (ES+) m/z 165 (MH+).
  • 2
  • [ 4360-63-8 ]
  • [ 959615-64-6 ]
  • [ 959615-65-7 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 7-fluoro-1,5-naphthyridin-2(1H)-one With sodium hydride In N,N-dimethyl-formamide at 20 - 60℃; for 1h; Stage #2: 2-bromomethyl-1,3-dioxolane In N,N-dimethyl-formamide at 85 - 95℃; for 4h; 7 To a suspension of 0.32 g of 7-fluoro-1,5-naphthyridin-2(1H)-one in 3 mL of N,N-dimethylformamide, 0.12 g of 60% sodium hydride was added at room temperature, and the mixture was stirred at 50 to 60°C for 1 hour. Thereto was added 0.60 mL of 2-bromomethyl-1,3-dioxolan, the temperature was increased to 85 to 95°C, and the reaction mixture was stirred for 4 hours. The reaction mixture was cooled to room temperature, and water and ethyl acetate were then added thereto. The organic layer was separated, and the aqueous layer was extracted with ethyl acetate. The organic layer and the extract were combined, the resultant solution was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. To the resultant residue, chloroform was added, the solid was filtered off and purified by flash silica gel column chromatography using gradient elution with hexane:ethyl acetate = 100:0 to 30:70 to obtain 0.23 g of 1-(1,3-dioxolan-2-ylmethyl)-7-fluoro-1,5-naphthyridin-2(1H)-one as a light yellow solid. 1H-NMR (CDCl3) δ: 3.84-3.93 (2H, m), 3.96-4.05 (2H, m), 4.45 (2H, d, J = 4.2 Hz), 5.19 (1H, t, J = 4.2 Hz), 6.88 (1H, d, J = 9.8 Hz), 7.69 (1H, dd, J = 10.5, 2.4 Hz), 7.90 (1H, d, J = 9.8 Hz), 8.41 (1H, d, J = 2.4 Hz)
  • 3
  • [ 959615-62-4 ]
  • [ 959615-64-6 ]
YieldReaction ConditionsOperation in experiment
With sodium methylate In methanol at 20℃; for 5.33333h; Heating / reflux; 6 To a solution of 0.36 g of ethyl (2E)-3-(3-amino-5-fluoropyridin-2-yl)acrylate in 3 mL of methanol, 0.37 g of a 28% sodium methoxide/methanol solution was added at room temperature, and the mixture was heated under reflux while stirring for 2 hours 40 minutes. Thereto was added 72 mg of a 28% sodium methoxide/methanol solution, and the mixture was heated under reflux while stirring for 1 hour. The reaction mixture was cooled to room temperature, the solvent was then distilled off under reduced pressure, and the resultant residue was charged with ethyl acetate and water and adjusted to pH 6.7 with 1 mol/L hydrochloric acid. The solvent was distilled off under reduced pressure, the solid was filtered off and washed with water and diethyl ether to obtain 0.17 g of 7-fluoro-1,5-naphthyridin-2(1H)-one as a light brown solid. 1H-NMR (DMSO-d6) δ: 6.72 (1H, d, J = 9.8 Hz), 7.47 (1H, dd, J = 9.6, 2.4 Hz), 7.94 (1H, d, J = 9.8 Hz), 8.50 (1H, d, J = 2.4 Hz), 11.99 (1H, brs)
  • 4
  • [ 884495-03-8 ]
  • [ 140-88-5 ]
  • [ 959615-64-6 ]
  • [ 959615-62-4 ]
YieldReaction ConditionsOperation in experiment
With triethylamine;bis(tri-t-butylphosphine)palladium(0); at 145 - 150℃; for 5.0h; To 0.99 g of <strong>[884495-03-8]2-bromo-5-fluoropyridin-3-amine</strong>, 0.67 mL of ethyl acrylate, 3.5 mL of triethylamine, and 0.13 g of bis(tri-tert-butylphosphine)palladium(0) were added, and the mixture was stirred at an external temperature of 145 to 150C for 5 hours in a sealed tube. The reaction mixture was cooled to room temperature and the solvent was distilled off under reduced pressure. The resultant residue was purified by flash silica gel column chromatography using gradient elution with chloroform:methanol = 100:0 to 90:10 to obtain 0.37 g of ethyl (2E)-3-(3-amino-5-fluoropyridin-2-yl)acrylate and 0.15 g of 7-fluoro-1,5-naphthyridin-2(1H)-one as light brown solids. Ethyl (2E)-3-(3-amino-5-fluoropyridin-2-yl)acrylate 1H-NMR (CDCl3) delta: 1.33 (3H, t, J = 7.1 Hz), 4.02-4.12 (2H, broad), 4.27 (2H, q, J = 7.1 Hz), 6.71 (1H, dd, J = 9.8, 2.4 Hz), 6.85 (1H, d, J = 15.1 Hz), 7.71 (1H, d, J = 15.1 Hz), 7.94 (1H, d, J = 2.4 Hz) 7-fluoro-1,5-naphthyridin-2(1H)-one 1H-NMR (DMSO-d6) delta: 6.72 (1H, dd, J = 9.8, 1.7 Hz), 7.47 (1H, dd, J = 9.6, 2.5 Hz), 7.94 (1H, d, J = 9.8 Hz), 8.50 (1H, d, J = 2.5 Hz), 11.99 (1H, s)
  • 5
  • [ 959617-75-5 ]
  • [ 959615-64-6 ]
YieldReaction ConditionsOperation in experiment
With water; potassium carbonate; p-toluenesulfonyl chloride In chloroform at 20℃; 220 To a solution of 60 mg of 7-fluoro-1,5-naphthyridine 1-oxide in 1.6 mL of chloroform, 84 mg of p-toluenesulfonyl chloride, 171 mg of potassium carbonate and 0.5 mL of water were added, and the mixture was stirred at room temperature overnight. The solid was filtered off, and purified by silica gel column chromatography using silica gel; Chromatorex-NH made by Fuji Silysia Chemical Ltd., and an eluent of chloroform:methanol = 10:1 to obtain 14 mg of 7-fluoro-1,5-naphthyridin-2(1H)-one as a white solid. 1H-NMR (CDCl3) δ: 6.71 (1H, d, J = 10.1 Hz), 7.29-7.57 (1H, m), 7.94 (1H, d, J = 10.1 Hz), 8.50 (1H, d, J = 2.3 Hz), 12.00 (1H, s)
  • 6
  • [ 959615-64-6 ]
  • trans-tert-butyl 4-(1-(2-nitrophenylsulfonyl)aziridin-2-yl)-cyclohexylcarbamate (-) enantiomer [ No CAS ]
  • trans-tert-butyl 4-(2-(7-fluoro-2-oxo-1,5-naphthyridin-1(2H)-yl)-1-(2-nitrophenylsulfonamido)ethyl)cyclohexylcarbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
27% Stage #1: 7-fluoro-1,5-naphthyridin-2(1H)-one With sodium hydride In N,N-dimethyl-formamide at 20℃; for 0.25h; Inert atmosphere; Cooling with ice; Stage #2: trans-tert-butyl 4-(1-(2-nitrophenylsulfonyl)aziridin-2-yl)-cyclohexylcarbamate (-) enantiomer In N,N-dimethyl-formamide 30 7-Fluoro-l,5-naphthyridin-2(lH)-one (prepared according to the procedure in WO07138974, 137 mg, 0.83 mmol) was suspended in dry DMF (1 mL) under nitrogen and cooled in an ice bath. Sodium hydride (40 mg, 1.0 mmol) was added and the reaction was removed from the ice bath, stirred at room temperature for 15 minutes. Trans-te/t-butyl 4-(l-(2-nitrophenylsulfonyl)- aziridin-2-yl)-cyclohexylcarbamate, ((-) enantiomer (Intermediate ll(b), 355 mg, 0.83 mmol) in 1.0 mL dry DMF was added dropwise. After 30 minutes the mixture was cooled in an ice bath and quenched with potassium phosphate buffer (IM, pΗ 7), diluted with water and extracted with ethyl acetate twice. The combined organic phases were washed with water (3 times 5 mL), then with brine, dried over sodium sulfate and concentrated under reduced pressure. Chromatography was done on silica gel with 20-100% ethyl acetate in hexanes giving 135 mg of product as a single enantiomer in the form of a yellow foam (27%). MS (ES): 612 (MNa+) for C27H32FN5O7S1H NMR (CDCl3) δ ppm 8.25 (s, IH), 7.96 (s, IH), 7.53 (m, 4H), 7.43 (t, IH), 7.31 (t, IH), 6.60 (d, IH), 6.38 (bs, IH), 4.56 (d, IH), 4.39 (m, IH), 4.12 (m,lH), 3.88 (m, IH), 3.26 (brs, IH), 1.75 (m, 2H), 1.58 (m, IH), 1.36 (brs, 10H), 1.06 (m, 3H)
  • 7
  • [ 959615-64-6 ]
  • [ 1378470-92-8 ]
YieldReaction ConditionsOperation in experiment
75% With trichlorophosphate In N,N-dimethyl-formamide; toluene at 110℃;
With thionyl chloride; N,N-dibutylformamide In toluene for 1h; Heating;
  • 8
  • [ 1159266-53-1 ]
  • [ 959615-64-6 ]
YieldReaction ConditionsOperation in experiment
102 g With sodium hydroxide In tert-butyl methyl ether; water
  • 9
  • [ 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]
  • 11
  • [ 959615-64-6 ]
  • 6-((1-(2-(7-methoxy-2-oxo-1,5-naphthyridin-1(2H)-yl)ethyl)-piperidin-4-ylamino)methyl)-3-methylpyrazine-2-carbonitrile bis(hydrochloride) [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: caesium carbonate / N,N-dimethyl-formamide / 90 °C 2.1: 1.5 h / 60 °C / Inert atmosphere 3.1: hydrogenchloride / 1,4-dioxane / 0.5 h / 70 °C 4.1: sodium carbonate / N,N-dimethyl-formamide / 0.03 h 4.2: 2 h / 70 °C 5.1: zinc diacetate; zinc; tris-(dibenzylideneacetone)dipalladium(0); 1,1'-bis-(diphenylphosphino)ferrocene / N,N-dimethyl-formamide / 1 h / 100 °C 5.2: 0 °C
  • 12
  • [ 959615-64-6 ]
  • [ 959616-29-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: caesium carbonate / N,N-dimethyl-formamide / 90 °C 2: 1.5 h / 60 °C / Inert atmosphere
Multi-step reaction with 4 steps 1: caesium carbonate / N,N-dimethyl-formamide / 4 h / 120 °C / Sealed tube 2: dichloromethane; pyridine / 0.5 h / -20 - 20 °C 3: potassium carbonate / N,N-dimethyl-formamide / 4 h / 100 °C / Sealed tube 4: methanol / 3 h / 65 °C
  • 14
  • [ 959615-64-6 ]
  • [ 959617-72-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: caesium carbonate / N,N-dimethyl-formamide / 90 °C 2: hydrogenchloride / 1,4-dioxane / 2 h / 80 °C
Multi-step reaction with 4 steps 1: caesium carbonate / N,N-dimethyl-formamide / 4 h / 120 °C / Sealed tube 2: dichloromethane; pyridine / 0.5 h / -20 - 20 °C 3: potassium carbonate / N,N-dimethyl-formamide / 4 h / 100 °C / Sealed tube 4: hydrogenchloride / dichloromethane; 1,4-dioxane / 1 h / 0 °C
Multi-step reaction with 4 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 20 - 60 °C 1.2: 4 h / 85 - 95 °C 2.1: water; trifluoroacetic acid / 4.08 h / 20 - 90 °C 2.2: pH 7.4 3.1: acetic acid / chloroform / 7.5 h / 20 °C 3.2: 10 h 4.1: hydrogenchloride / ethanol; chloroform / 40 h / 20 - 40 °C
  • 15
  • [ 959615-64-6 ]
  • [ 959616-35-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: caesium carbonate / N,N-dimethyl-formamide / 90 °C 2: 1.5 h / 60 °C / Inert atmosphere 3: hydrogenchloride / 1,4-dioxane / 0.5 h / 70 °C
Multi-step reaction with 5 steps 1: caesium carbonate / N,N-dimethyl-formamide / 4 h / 120 °C / Sealed tube 2: dichloromethane; pyridine / 0.5 h / -20 - 20 °C 3: potassium carbonate / N,N-dimethyl-formamide / 4 h / 100 °C / Sealed tube 4: methanol / 3 h / 65 °C 5: hydrogenchloride / dichloromethane; 1,4-dioxane / 1 h / 0 °C
  • 16
  • [ 959615-64-6 ]
  • [ 1610628-07-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: caesium carbonate / dimethyl sulfoxide / 0.17 h / 20 °C 1.2: 90 °C 2.1: triethylamine / dichloromethane / 0.5 h / Inert atmosphere; Cooling with ice
Multi-step reaction with 2 steps 1.1: caesium carbonate / dimethyl sulfoxide / 0.17 h / 20 °C 1.2: 20 - 90 °C 2.1: triethylamine / dichloromethane / 0.5 h / 0 °C / Inert atmosphere
  • 17
  • [ 959615-64-6 ]
  • [ 1610628-09-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: caesium carbonate / dimethyl sulfoxide / 0.17 h / 20 °C 1.2: 90 °C 2.1: methanol / 2 h / 75 °C 3.1: triethylamine / dichloromethane / Inert atmosphere 3.2: 0.75 h / 0 °C
Multi-step reaction with 3 steps 1.1: caesium carbonate / dimethyl sulfoxide / 0.17 h / 20 °C 1.2: 20 - 90 °C 2.1: sodium methylate / 2 h / 75 °C 3.1: triethylamine / dichloromethane / 0.75 h / 0 °C / Inert atmosphere
  • 19
  • [ 959615-64-6 ]
  • [ 1613053-67-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: caesium carbonate / dimethyl sulfoxide / 0.17 h / 20 °C 1.2: 20 - 90 °C 2.1: triethylamine / dichloromethane / 0.5 h / 0 °C / Inert atmosphere 3.1: sodium carbonate / N,N-dimethyl-formamide / 3 h / 92 °C
Multi-step reaction with 3 steps 1: caesium carbonate / N,N-dimethyl-formamide / 4 h / Sealed tube 2: pyridine / dichloromethane / -20 °C 3: potassium carbonate / N,N-dimethyl-formamide / 4 h / 100 °C / Sealed tube
  • 20
  • [ 959615-64-6 ]
  • [ 1613053-68-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: caesium carbonate / dimethyl sulfoxide / 0.17 h / 20 °C 1.2: 20 - 90 °C 2.1: triethylamine / dichloromethane / 0.5 h / 0 °C / Inert atmosphere 3.1: sodium carbonate / N,N-dimethyl-formamide / 3 h / 92 °C 4.1: sodium methylate / 70 °C / Inert atmosphere
Multi-step reaction with 4 steps 1: caesium carbonate / N,N-dimethyl-formamide / 4 h / Sealed tube 2: pyridine / dichloromethane / -20 °C 3: potassium carbonate / N,N-dimethyl-formamide / 4 h / 100 °C / Sealed tube 4: methanol / 3 h / 65 °C
  • 21
  • [ 959615-64-6 ]
  • [ 1613053-69-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: caesium carbonate / dimethyl sulfoxide / 0.17 h / 20 °C 1.2: 20 - 90 °C 2.1: triethylamine / dichloromethane / 0.5 h / 0 °C / Inert atmosphere 3.1: sodium carbonate / N,N-dimethyl-formamide / 3 h / 92 °C 4.1: hydrogenchloride / 1,4-dioxane / 2 h / 80 °C
  • 22
  • [ 959615-64-6 ]
  • [ 1613053-70-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: caesium carbonate / dimethyl sulfoxide / 0.17 h / 20 °C 1.2: 20 - 90 °C 2.1: triethylamine / dichloromethane / 0.5 h / 0 °C / Inert atmosphere 3.1: sodium carbonate / N,N-dimethyl-formamide / 3 h / 92 °C 4.1: sodium methylate / 70 °C / Inert atmosphere 5.1: hydrogenchloride / 1,4-dioxane / 2 h / 80 °C
Multi-step reaction with 5 steps 1: caesium carbonate / N,N-dimethyl-formamide / 4 h / Sealed tube 2: pyridine / dichloromethane / -20 °C 3: potassium carbonate / N,N-dimethyl-formamide / 4 h / 100 °C / Sealed tube 4: methanol / 3 h / 65 °C 5: hydrogenchloride / dichloromethane; 1,4-dioxane / 0 °C
  • 23
  • [ 959615-64-6 ]
  • [ 1613053-75-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: caesium carbonate / dimethyl sulfoxide / 0.17 h / 20 °C 1.2: 20 - 90 °C 2.1: sodium methylate / 2 h / 75 °C 3.1: triethylamine / dichloromethane / 0.75 h / 0 °C / Inert atmosphere 4.1: sodium carbonate / N,N-dimethyl-formamide / 2 h / 90 °C
  • 24
  • [ 959615-64-6 ]
  • [ 1613053-76-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: caesium carbonate / dimethyl sulfoxide / 0.17 h / 20 °C 1.2: 20 - 90 °C 2.1: sodium methylate / 2 h / 75 °C 3.1: triethylamine / dichloromethane / 0.75 h / 0 °C / Inert atmosphere 4.1: sodium carbonate / N,N-dimethyl-formamide / 2 h / 90 °C
  • 25
  • [ 959615-64-6 ]
  • [ 1613053-77-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: caesium carbonate / dimethyl sulfoxide / 0.17 h / 20 °C 1.2: 20 - 90 °C 2.1: sodium methylate / 2 h / 75 °C 3.1: triethylamine / dichloromethane / 0.75 h / 0 °C / Inert atmosphere 4.1: sodium carbonate / N,N-dimethyl-formamide / 2 h / 90 °C
  • 26
  • [ 959615-64-6 ]
  • [ 1613053-78-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: caesium carbonate / dimethyl sulfoxide / 0.17 h / 20 °C 1.2: 20 - 90 °C 2.1: sodium methylate / 2 h / 75 °C 3.1: triethylamine / dichloromethane / 0.75 h / 0 °C / Inert atmosphere 4.1: sodium carbonate / N,N-dimethyl-formamide / 2 h / 90 °C
  • 27
  • [ 959615-64-6 ]
  • [ 1613053-79-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: caesium carbonate / dimethyl sulfoxide / 0.17 h / 20 °C 1.2: 20 - 90 °C 2.1: triethylamine / dichloromethane / 0.5 h / 0 °C / Inert atmosphere 3.1: sodium carbonate / N,N-dimethyl-formamide / 3 h / 92 °C 4.1: sodium methylate / 70 °C / Inert atmosphere 5.1: hydrogenchloride / 1,4-dioxane / 2 h / 80 °C 6.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 2 h / 130 °C / Microwave irradiation
  • 28
  • [ 959615-64-6 ]
  • [ 1613053-80-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: caesium carbonate / dimethyl sulfoxide / 0.17 h / 20 °C 1.2: 20 - 90 °C 2.1: triethylamine / dichloromethane / 0.5 h / 0 °C / Inert atmosphere 3.1: sodium carbonate / N,N-dimethyl-formamide / 3 h / 92 °C 4.1: sodium methylate / 70 °C / Inert atmosphere 5.1: hydrogenchloride / 1,4-dioxane / 2 h / 80 °C 6.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 2 h / 130 °C / Microwave irradiation
  • 29
  • [ 959615-64-6 ]
  • [ 1613053-81-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: caesium carbonate / dimethyl sulfoxide / 0.17 h / 20 °C 1.2: 20 - 90 °C 2.1: triethylamine / dichloromethane / 0.5 h / 0 °C / Inert atmosphere 3.1: sodium carbonate / N,N-dimethyl-formamide / 3 h / 92 °C 4.1: hydrogenchloride / 1,4-dioxane / 2 h / 80 °C 5.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 2 h / 130 °C / Microwave irradiation
  • 30
  • [ 959615-64-6 ]
  • [ 1613053-82-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: caesium carbonate / dimethyl sulfoxide / 0.17 h / 20 °C 1.2: 20 - 90 °C 2.1: triethylamine / dichloromethane / 0.5 h / 0 °C / Inert atmosphere 3.1: sodium carbonate / N,N-dimethyl-formamide / 2 h / 90 °C
  • 31
  • [ 959615-64-6 ]
  • [ 1613053-83-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: caesium carbonate / dimethyl sulfoxide / 0.17 h / 20 °C 1.2: 20 - 90 °C 2.1: triethylamine / dichloromethane / 0.5 h / 0 °C / Inert atmosphere 3.1: sodium carbonate / N,N-dimethyl-formamide / 2 h / 90 °C
  • 32
  • [ 959615-64-6 ]
  • [ 1613053-84-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: caesium carbonate / dimethyl sulfoxide / 0.17 h / 20 °C 1.2: 20 - 90 °C 2.1: sodium methylate / 2 h / 75 °C 3.1: triethylamine / dichloromethane / 0.75 h / 0 °C / Inert atmosphere 4.1: sodium carbonate / N,N-dimethyl-formamide / 2 h / 90 °C
  • 33
  • [ 959615-64-6 ]
  • [ 1613053-85-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: caesium carbonate / dimethyl sulfoxide / 0.17 h / 20 °C 1.2: 20 - 90 °C 2.1: sodium methylate / 2 h / 75 °C 3.1: triethylamine / dichloromethane / 0.75 h / 0 °C / Inert atmosphere 4.1: sodium carbonate / N,N-dimethyl-formamide / 2 h / 90 °C
  • 34
  • [ 959615-64-6 ]
  • [ 1613053-86-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: caesium carbonate / dimethyl sulfoxide / 0.17 h / 20 °C 1.2: 20 - 90 °C 2.1: sodium methylate / 2 h / 75 °C 3.1: triethylamine / dichloromethane / 0.75 h / 0 °C / Inert atmosphere 4.1: sodium carbonate / N,N-dimethyl-formamide / 2 h / 90 °C
  • 35
  • [ 959615-64-6 ]
  • [ 1613053-87-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: caesium carbonate / dimethyl sulfoxide / 0.17 h / 20 °C 1.2: 20 - 90 °C 2.1: sodium methylate / 2 h / 75 °C 3.1: triethylamine / dichloromethane / 0.75 h / 0 °C / Inert atmosphere 4.1: sodium carbonate / N,N-dimethyl-formamide / 2 h / 90 °C
  • 36
  • [ 959615-64-6 ]
  • [ 1613053-88-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: caesium carbonate / dimethyl sulfoxide / 0.17 h / 20 °C 1.2: 20 - 90 °C 2.1: triethylamine / dichloromethane / 0.5 h / 0 °C / Inert atmosphere 3.1: sodium carbonate / N,N-dimethyl-formamide / 2 h / 90 °C
  • 37
  • [ 959615-64-6 ]
  • [ 1613053-90-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: caesium carbonate / dimethyl sulfoxide / 0.17 h / 20 °C 1.2: 20 - 90 °C 2.1: triethylamine / dichloromethane / 0.5 h / 0 °C / Inert atmosphere 3.1: sodium carbonate / N,N-dimethyl-formamide / 2 h / 90 °C
  • 38
  • [ 959615-64-6 ]
  • [ 1613053-91-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: caesium carbonate / dimethyl sulfoxide / 0.17 h / 20 °C 1.2: 20 - 90 °C 2.1: sodium methylate / 2 h / 75 °C 3.1: triethylamine / dichloromethane / 0.75 h / 0 °C / Inert atmosphere 4.1: sodium carbonate / N,N-dimethyl-formamide / 2 h / 90 °C
  • 39
  • [ 959615-64-6 ]
  • [ 1613053-92-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: caesium carbonate / dimethyl sulfoxide / 0.17 h / 20 °C 1.2: 20 - 90 °C 2.1: triethylamine / dichloromethane / 0.5 h / 0 °C / Inert atmosphere 3.1: sodium carbonate / N,N-dimethyl-formamide / 3 h / 92 °C 4.1: sodium methylate / 70 °C / Inert atmosphere 5.1: hydrogenchloride / 1,4-dioxane / 2 h / 80 °C 6.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 2 h / 130 °C / Microwave irradiation
  • 40
  • [ 959615-64-6 ]
  • [ 1613053-93-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: caesium carbonate / dimethyl sulfoxide / 0.17 h / 20 °C 1.2: 20 - 90 °C 2.1: triethylamine / dichloromethane / 0.5 h / 0 °C / Inert atmosphere 3.1: sodium carbonate / N,N-dimethyl-formamide / 2 h / 90 °C 4.1: caesium carbonate / dimethyl sulfoxide / 0.5 h / 20 °C 4.2: 120 °C
  • 41
  • [ 959615-64-6 ]
  • [ 1613053-94-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: caesium carbonate / dimethyl sulfoxide / 0.17 h / 20 °C 1.2: 20 - 90 °C 2.1: triethylamine / dichloromethane / 0.5 h / 0 °C / Inert atmosphere 3.1: sodium carbonate / N,N-dimethyl-formamide / 2 h / 90 °C 4.1: caesium carbonate / dimethyl sulfoxide / 0.5 h / 20 °C 4.2: 120 °C
Multi-step reaction with 6 steps 1.1: caesium carbonate / dimethyl sulfoxide / 0.17 h / 20 °C 1.2: 20 - 90 °C 2.1: triethylamine / dichloromethane / 0.5 h / 0 °C / Inert atmosphere 3.1: sodium carbonate / N,N-dimethyl-formamide / 3 h / 92 °C 4.1: hydrogenchloride / 1,4-dioxane / 2 h / 80 °C 5.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 2 h / 130 °C / Microwave irradiation 6.1: caesium carbonate / dimethyl sulfoxide / 0.5 h / 20 °C 6.2: 120 °C
  • 42
  • [ 141-32-2 ]
  • [ 884495-37-8 ]
  • [ 959615-64-6 ]
YieldReaction ConditionsOperation in experiment
53% With N-Methyldicyclohexylamine; palladium diacetate; Tetra(tert-butyl)phosphonium-tetrafluoroborat; at 150℃; for 4h;Inert atmosphere; To a stirred mixture of substituted<strong>[884495-37-8]2-chloro-5-fluoropyridin-3-amine</strong> (5) (2 g, 13.65 mmol) and butyl acrylate (2.09g, 16.38mmol) in cumene (10mL) at room temperature, was added N-methyldicyclohexylamine (7.99 g, 40.9 4 mmol), followed by catalytic amounts of tri tert-butyl phosphoniumtetrafluroborate (0.158 g, 0.546 mmol). This reaction mixture was purged for 5 min with argon followed by the addition of Pd(OAc)2 (0.061 g, 0.273 mmol). The reaction mixture was heated at 150C for 4h (monitored by TLC & LCMS for completion), and the reaction mixture was filtered through celite bed and solvent was evaporated under reduced pressure. The reaction mixture was further extracted with ethyl acetate (3×40mL). 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 residue was purified by silica gel column chromatography using hexane: ethyl acetate as eluent to give 7-fluoro-1, 5-naphthyridin-2(1H)-one (6) (1.23 g, 53 %) as brown solid. M.p: 282-284C. 1H NMR [300MHz, DMSO-d6]: deltaH12.31 (s, 1H), 8.21-6.95 (m, 4H). 13C NMR [100MHz, DMSO-d6] deltac: 163.5, 157.9, 142.8, 140.5, 132.3, 127.1, 123.2, 110.2 ESI-MS m/z 165 (M+H)+. Anal Calcd for C8H5FN2O: C, 58.54; H, 3.07; N, 17.07; Found: C, 58.58; H, 3.12; N, 17.03.
  • 43
  • [ 959615-64-6 ]
  • [ 1623153-48-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: caesium carbonate / N,N-dimethyl-formamide / 4 h / 120 °C / Sealed tube 2: dichloromethane; pyridine / 0.5 h / -20 - 20 °C
Multi-step reaction with 2 steps 1: caesium carbonate / N,N-dimethyl-formamide / 4 h / Sealed tube 2: pyridine / dichloromethane / -20 °C
  • 44
  • [ 959615-64-6 ]
  • [ 959616-74-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: caesium carbonate / N,N-dimethyl-formamide / 4 h / 120 °C / Sealed tube 2: dichloromethane; pyridine / 0.5 h / -20 - 20 °C 3: potassium carbonate / N,N-dimethyl-formamide / 4 h / 100 °C / Sealed tube
Multi-step reaction with 3 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 20 - 60 °C 1.2: 4 h / 85 - 95 °C 2.1: water; trifluoroacetic acid / 4.08 h / 20 - 90 °C 2.2: pH 7.4 3.1: acetic acid / chloroform / 7.5 h / 20 °C 3.2: 10 h
  • 45
  • C15H13FN2O2 [ No CAS ]
  • [ 959615-64-6 ]
YieldReaction ConditionsOperation in experiment
99% With tributylphosphine; acetic acid at 110℃;
  • 46
  • [ 959615-64-6 ]
  • [ 1003944-32-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: trichlorophosphate / N,N-dimethyl-formamide; toluene / 110 °C 2: toluene / 50 °C
  • 47
  • [ 959615-64-6 ]
  • [ 1373311-88-6 ]
  • (R)-trans-tert-butyl 4-(2-(7-fluoro-2-oxo-1,5-naphthyridin-1(2H)-yl)-1-(2-nitrophenylsulfonamido)ethyl)cyclohexylcarbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
720 mg Stage #1: 7-fluoro-1,5-naphthyridin-2(1H)-one With sodium hydride In N,N-dimethyl-formamide at 20℃; for 0.25h; Inert atmosphere; Stage #2: tert-butyl (1R,4r)-4-[(R)-1-(2-nitrophenylsulfonyl)aziridin-2-yl]cyclohexylcarbamate In N,N-dimethyl-formamide at 20℃; Inert atmosphere; 7. General procedure for 4, by alkylation of 2 General procedure: To a solution of 2 (2 mmol) in DMF (10 mL) was added sodium hydride (120 mg, 3.0 mmol), and the mixture was stirred at roomtem perature for 15 min under nitrogen. A solution of 3 (850 mg,2.00 mmol) in DMF (6 mL) was added and the mixture was stirredat room temperature over night. The mixture was quenched withice water and extracted with ethyl acetate (100 mL). The organic phase was washed with brine twice (100 mL) and dried over magnesium sulfate, then concentrated under reduced pressure. 7.7. (R)-trans-tert-Butyl 4-(2-(7-fluoro-2-oxo-1,5-naphthyridin-1(2H)-yl)-1-(2-nitrophenylsulfonamido)ethyl)cyclohexylcarbamate (4g); 7-Fluoro-1,5-naphthyridin-2(1H)-one 2 g52 (680 mg, 4.14mmol) was reacted with sodium hydride (199 mg, 4.97 mmol) and 3, (R) isomer, (1.76 g, 4.14 mmol) following the general procedure for 4. Chromatography was done on silica gel with 20-100% ethyl acetate in hexanes to give 720 mg of the product as a yellow foam.
  • 48
  • [ 724788-70-9 ]
  • [ 959615-64-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: hydrogen; sodium hydrogencarbonate / palladium 10% on activated carbon / methanol / 4 h / 760.05 Torr 2.1: hydrogen bromide; acetic acid / 18 h / 20 °C 2.2: 1 h / 20 °C / pH 4
  • 49
  • [ 14756-77-5 ]
  • [ 959615-64-6 ]
  • 50
  • [ 959615-64-6 ]
  • [ 959617-47-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 20 - 60 °C 1.2: 4 h / 85 - 95 °C 2.1: sodium hydroxide; water / tetrahydrofuran / 9 h / Heating / reflux 3.1: sodium hydroxide / tetrabutylammomium bromide / water; N,N-dimethyl-formamide; toluene / 4.5 h
  • 51
  • [ 884495-03-8 ]
  • [ 959615-64-6 ]
  • 52
  • [ 17965-71-8 ]
  • [ 959615-64-6 ]
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