Name: 959615-64-6|7-Fluoro-1,5-naphthyridin-2(1H)-one|95%
Brand: Ambeed
SKU: A418995
Rating: 94 (27 reviews)

1
[ 1003944-32-8 ]
[ 959615-64-6 ]

Yield	Reaction Conditions	Operation 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+).

Reference： [1]Current Patent Assignee: GLAXOSMITHKLINE PLC - WO2008/9700, 2008, A1 Location in patent: Page/Page column 41

2
[ 4360-63-8 ]
[ 959615-64-6 ]
[ 959615-65-7 ]

Yield	Reaction Conditions	Operation 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)

Reference： [1]Current Patent Assignee: TAISHO PHARMACEUTICAL HOLDINGS CO., LTD.; FUJIFILM HOLDINGS CORP. - EP2022793, 2009, A1 Location in patent: Page/Page column 33

3
[ 959615-62-4 ]
[ 959615-64-6 ]

Yield	Reaction Conditions	Operation 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)

Reference： [1]Current Patent Assignee: TAISHO PHARMACEUTICAL HOLDINGS CO., LTD.; FUJIFILM HOLDINGS CORP. - EP2022793, 2009, A1 Location in patent: Page/Page column 32-33

4
[ 884495-03-8 ]
[ 140-88-5 ]
[ 959615-64-6 ]
[ 959615-62-4 ]

Yield	Reaction Conditions	Operation 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)

Reference： [1]Patent: EP2022793,2009,A1 .Location in patent: Page/Page column 32

5
[ 959617-75-5 ]
[ 959615-64-6 ]

Yield	Reaction Conditions	Operation 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)

Reference： [1]Current Patent Assignee: TAISHO PHARMACEUTICAL HOLDINGS CO., LTD.; FUJIFILM HOLDINGS CORP. - EP2022793, 2009, A1 Location in patent: Page/Page column 108

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 ]

Yield	Reaction Conditions	Operation 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)

Reference： [1]Current Patent Assignee: ASTRAZENECA PLC - WO2010/55348, 2010, A1 Location in patent: Page/Page column 58

7
[ 959615-64-6 ]
[ 1378470-92-8 ]

Yield	Reaction Conditions	Operation in experiment
75%	With trichlorophosphate In N,N-dimethyl-formamide; toluene at 110℃;
	With thionyl chloride; N,N-dibutylformamide In toluene for 1h; Heating;

Reference： [1]Abele, Stefan; Schmidt, Gunther; Fleming, Matthew J.; Steiner, Heinz [Organic Process Research and Development, 2014, vol. 18, # 8, p. 993 - 1001]
[2]Voight, Eric A.; Yin, Hao; Downing, Susan V.; Calad, Stacie A.; Matsuhashi, Hayao; Giordano, Ilaria; Hennessy, Alan J.; Goodman, Richard M.; Wood, Jeffery L. [Organic Letters, 2010, vol. 12, # 15, p. 3422 - 3425]

8
[ 1159266-53-1 ]
[ 959615-64-6 ]

Yield	Reaction Conditions	Operation in experiment
102 g	With sodium hydroxide In tert-butyl methyl ether; water

Reference： [1]Voight, Eric A.; Yin, Hao; Downing, Susan V.; Calad, Stacie A.; Matsuhashi, Hayao; Giordano, Ilaria; Hennessy, Alan J.; Goodman, Richard M.; Wood, Jeffery L. [Organic Letters, 2010, vol. 12, # 15, p. 3422 - 3425]

9
[ 959615-64-6 ]
[ 540-51-2 ]
[ 1351401-26-7 ]

Yield	Reaction Conditions	Operation 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]

10
[ 141-32-2 ]
[ 884495-03-8 ]
[ 959615-64-6 ]

Reference： [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 4889 - 4905
[2]ACS Medicinal Chemistry Letters,2014,vol. 5,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 ]

Yield	Reaction Conditions	Operation 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

Reference： [1]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]

12
[ 959615-64-6 ]
[ 959616-29-6 ]

Yield	Reaction Conditions	Operation 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

Reference： [1]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]
[2]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]

13
[ 959615-64-6 ]
[ 1610628-08-4 ]

Yield	Reaction Conditions	Operation 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: methanol / 2 h / 75 °C
	Multi-step reaction with 2 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

Reference： [1]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]
[2]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]

14
[ 959615-64-6 ]
[ 959617-72-2 ]

Yield	Reaction Conditions	Operation 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

Reference： [1]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]
[2]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]
[3]Current Patent Assignee: TAISHO PHARMACEUTICAL HOLDINGS CO., LTD.; FUJIFILM HOLDINGS CORP. - EP2022793, 2009, A1

15
[ 959615-64-6 ]
[ 959616-35-4 ]

Yield	Reaction Conditions	Operation 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

Reference： [1]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]
[2]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]

16
[ 959615-64-6 ]
[ 1610628-07-3 ]

Yield	Reaction Conditions	Operation 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

Reference： [1]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]
[2]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]

17
[ 959615-64-6 ]
[ 1610628-09-5 ]

Yield	Reaction Conditions	Operation 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

Reference： [1]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]
[2]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]

18
[ 917341-20-9 ]
[ 959615-64-6 ]
[ 959616-74-1 ]

Yield	Reaction Conditions	Operation in experiment
78%	With caesium carbonate In N,N-dimethyl-formamide at 90℃;

Reference： [1]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]

19
[ 959615-64-6 ]
[ 1613053-67-0 ]

Yield	Reaction Conditions	Operation 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

Reference： [1]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]
[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]

20
[ 959615-64-6 ]
[ 1613053-68-1 ]

Yield	Reaction Conditions	Operation 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

Reference： [1]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]
[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]

21
[ 959615-64-6 ]
[ 1613053-69-2 ]

Yield	Reaction Conditions	Operation 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

Reference： [1]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]

22
[ 959615-64-6 ]
[ 1613053-70-5 ]

Yield	Reaction Conditions	Operation 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

Reference： [1]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]
[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]

23
[ 959615-64-6 ]
[ 1613053-75-0 ]

Yield	Reaction Conditions	Operation 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

Reference： [1]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]

24
[ 959615-64-6 ]
[ 1613053-76-1 ]

Yield	Reaction Conditions	Operation 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

Reference： [1]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]

25
[ 959615-64-6 ]
[ 1613053-77-2 ]

Yield	Reaction Conditions	Operation 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

Reference： [1]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]

26
[ 959615-64-6 ]
[ 1613053-78-3 ]

Yield	Reaction Conditions	Operation 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

Reference： [1]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]

27
[ 959615-64-6 ]
[ 1613053-79-4 ]

Yield	Reaction Conditions	Operation 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

Reference： [1]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]

28
[ 959615-64-6 ]
[ 1613053-80-7 ]

Yield	Reaction Conditions	Operation 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

Reference： [1]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]

29
[ 959615-64-6 ]
[ 1613053-81-8 ]

Yield	Reaction Conditions	Operation 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

Reference： [1]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]

30
[ 959615-64-6 ]
[ 1613053-82-9 ]

Yield	Reaction Conditions	Operation 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

Reference： [1]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]

31
[ 959615-64-6 ]
[ 1613053-83-0 ]

Yield	Reaction Conditions	Operation 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

Reference： [1]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]

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
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CAS No. :	959615-64-6	MDL No. :	MFCD18836778
Formula :	C₈H₅FN₂O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	164.14 g/mol	Pubchem ID :	-
Synonyms :

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:

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 959615-64-6 ]

Quality Control of [ 959615-64-6 ]

Related Doc. of [ 959615-64-6 ]

Product Details of [ 959615-64-6 ]

Safety of [ 959615-64-6 ]

Application In Synthesis of [ 959615-64-6 ]

[ 959615-64-6 ] Synthesis Path-Downstream 1~31

Related Functional Groups of
[ 959615-64-6 ]

Amides

Related Parent Nucleus of
[ 959615-64-6 ]

Naphthyridines

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

[ CAS No. 959615-64-6 ]

Quality Control of [ 959615-64-6 ]

Related Doc. of [ 959615-64-6 ]

Product Details of [ 959615-64-6 ]

Safety of [ 959615-64-6 ]

Application In Synthesis of [ 959615-64-6 ]

[ 959615-64-6 ] Synthesis Path-Downstream 1~31

Related Functional Groups of [ 959615-64-6 ]

Amides

Related Parent Nucleus of [ 959615-64-6 ]

Naphthyridines

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 959615-64-6 ]

Related Parent Nucleus of
[ 959615-64-6 ]