Name: 3660-90-0|1,4-Dibromophthalazine|95%
Brand: Ambeed
SKU: A802914
Rating: 90 (35 reviews)

1
[ 1445-69-8 ]
[ 3660-90-0 ]
[ 19064-73-4 ]

Reference： [1]Journal fur praktische Chemie (Leipzig 1954),1932,vol. <2> 135,p. 128,131
[2]Journal fur praktische Chemie (Leipzig 1954),1932,vol. <2> 135,p. 128,131
[3]Journal of Medicinal Chemistry,2011,vol. 54,p. 312 - 319

2
[ 1445-69-8 ]
[ 7789-69-7 ]
[ 3660-90-0 ]
[ 19064-73-4 ]

Yield	Reaction Conditions	Operation in experiment
	In 1,2-dichloro-ethane; for 48h;Heating / reflux;	Example E- 1 : 2-Benzyl-4- f 5-methyl- lH-pyrazol-3-ylaminalpha V2H-phthalazin- 1 -one4-Bromo-2H-phthalazin- 1 -one2,3-Dihydro-l,4-phthalazinedione (12.5g, 78mmol) was suspended in dichloroethane (200ml) and phosphorous pentabromide (50.Og, 116mmol) was added in one portion and the reaction heated to reflux for 24 hours. A further portion of phosphorous pentabromide (20.Og, 70mol) was added and the reaction heated for a further 24 hours. The reaction was cooled to room temperature and poured into ice water. The resulting precipitate was filtered and washed with water to give a crude mixture of mono and dibrominated product (22.8g).

Reference： [1]Patent: WO2006/32518,2006,A1 .Location in patent: Page/Page column 154

3
[ 3660-90-0 ]
[ 19064-73-4 ]

Yield	Reaction Conditions	Operation in experiment
60%		This crude material was suspended in acetic acid (230.OmL) and heated to 12O0C for 2 hrs. The reaction was cooled to room temperature and poured into ice water EPO <DP n="156"/>and the resulting precipitate filtered. The solid was washed with water and dried to give the title compound (10.4g, 60% yield) as a white solid. 1H-NMR: (400 MHz, D6-DMSO), 12.95 (IH, s), 8.25 (IH, dd), 8.03 (IH, ddd), 7.96-7.90-(2H, m); MS (ESI+) = (M+H)+ 225 & 227

Reference： [1]Patent: WO2006/32518,2006,A1 .Location in patent: Page/Page column 154; 155
[2]Bioorganic and Medicinal Chemistry,2018,vol. 26,p. 3217 - 3226

4
[ 3660-90-0 ]
[ 108612-54-0 ]
[ 1258861-47-0 ]

Yield	Reaction Conditions	Operation in experiment
95%	With potassium carbonate; In 1-methyl-pyrrolidin-2-one; at 80℃;	Preparation 5 tert-Butyl 1-(4-bromophthalazin-1-yl)piperidin-4-yl(methyl)carbamateCombine 1,4-dibromophthalazine (0.70 g, 2.38 mmol), N-methylpyrrolidone (7.0 mL), potassium carbonate (395 mg, 2.86 mmol), and methyl-piperidin-4-yl-carbamic acid tert-butyl ester (532 mg, 2.38 mmol). Heat at 80 C. overnight. Cool and pour into water. Collect the solid and dry in a vacuum oven at ambient temperature overnight to obtain the final product (0.96 g, 95%). ES/MS m/z (81Br) 421.0 (M+1).

Reference： [1]Patent: US2010/324048,2010,A1 .Location in patent: Page/Page column 4

5
[ 1445-69-8 ]
[ 3660-90-0 ]

Yield	Reaction Conditions	Operation in experiment
93%	With phosphorus pentabromide at 140℃; Sealed tube;	4 Preparation 41,4-DibromophthalazineCharge a pressure tube with phosphorus pentabromide (24.5 g, 54 1 mmol) and 2,3-dihydro-phthalazine-1,4-dione (5.00 g, 30.8 mmol). Seal the tube and heat at 140° C. for 6-7 h. Allow to cool overnight. Carefully open the tube due to pressure. Chisel out the solid and pour into ice water. Allow to stir in ice water and collect the resulting solid by vacuum filtration. Dry in a vacuum oven to obtain the final product (8.31 g, 93%). ES/MS (79Br, 81Br) m/z 288.8 (M+). Ref.: Can. J. Chem. 1965, 43, 2708.
88%	With phosphorus(V) oxybromide In 1,2-dichloro-ethane at 100℃; for 18h;	4.1.1. Synthesis of 1,4-dibromophthalazine (2) Phosphorus oxybromide (861 mg, 3.0 mmol) was added to a stirred suspension of 2,3-dihydrophthalazine-1,4-dione (162 mg, 1.0 mmol) in 1,2-dichloroethane (5 mL). The mixture was heated to 100 °C for 18 h and poured into water (100 mL) upon cooling to rt The aqueous layer was neutralized with saturated Na2CO3 solution and concentrated to give a residue, which was washed with water to afford the product as a white solid. Yield: 88%, m.p. 160.1-161.6 °C. 1H NMR (400 MHz, CDCl3) δ (ppm): 8.37-8.33 (m, 2H), 8.12-8.08 (m, 2H). GC-MS (EI): m/z calc. 285.8, m/z found 285.8.
83%	With phosphorus(V) oxybromide In 1,2-dichloro-ethane at 100℃; for 18h;	1.1 1) Intermediate product synthesis phosphorus oxybromide (53.1 g, 185.0 mmol) was slowly added dropwise. For 18 hours and the mixture was stirred for 100 deg C . The reaction solution was cooled to room temperature, and the reaction solution was poured into distilled water. The aqueous solution was neutralized with saturated Na2CO3 solution and the product was washed several times with distilled water to give a yield of 83% white solid.

71%	With carbon tetrabromide; phosphorus pentabromide at 80 - 130℃; for 6h;	2 Synthesis of 1,4-dibromophthalazine The title compound was prepared using a modification of a previously reported procedure [30]. To a round bottomed flask equipped with a stir bar and reflux condenser was added a mixture of 1,4-phthalahydrazide (1.375g, 8.49mmol) and carbon tetrabromide (85g). The reaction mixture was heated to 80°C and phosphorous pentabromide (9.135g, 21.2mmol, 2.5eq.) introduced. The temperature was then raised to 130°C and stirred at this temperature for 6h. After cooling to room temperature, the solid mass was treated with CH2Cl2 (60mL) until all lumps had been disintegrated to form a suspension. This mixture was then added to ice water (250mL) and stirred overnight. The organic layer was extracted and dried over magnesium sulfate. Following filtration, the filtrate was concentrated until a paste was formed; the paste was filtered and washed with copious amounts of hexane. The crude product was recrystallised from hot THF and left to stand at -30°C overnight. The yellow needles were collected and dried; additional crops of the product were combined (71%, 1.721g). Mp: 156-158°C (lit. [30]: 160°C). 1H NMR (300MHz, CDCl3, 298K): δ 8.05 (dd, J(HH) 6.3, 3.0, Ar-H), 8.29 (dd, J(HH) 6.3, 3.0, Ar-H). IR (cm-1) 2353 (br s), 1873 (br m), 1601 (w), 1558 (m), 1496 (w), 1471 (s), 1404 (s), 1344 (m), 1295 (s), 1255 (s), 1151 (w), 1139 (w), 1055 (w), 993 (s), 944 (m), 796 (s), 773 (s). FABMS: m/z 288 [M]+. HRMS (FAB): calcd for C8H5N279Br2 [M+H]+ 286.88195, found 286.88190.
	With phosphorus(V) oxybromide In 1,2-dichloro-ethane Reflux;
	With phosphorus(V) oxybromide In 1,2-dichloro-ethane Reflux;

Reference： [1]Current Patent Assignee: ELI LILLY & CO - US2010/324048, 2010, A1 Location in patent: Page/Page column 4
[2]Gao, Rui; Liao, Sha; Zhang, Chen; Zhu, Weilong; Wang, Liyan; Huang, Jin; Zhao, Zhenjiang; Li, Honglin; Qian, Xuhong; Xu, Yufang [European Journal of Medicinal Chemistry, 2013, vol. 62, p. 597 - 604]
[3]Current Patent Assignee: LG DISPLAY CO.,LTD. - KR2017/79353, 2017, A Location in patent: Paragraph 0256; 0257-0259
[4]Savjani, Nicky; Singh, Kuldip; Solan, Gregory A. [Inorganica Chimica Acta, 2015, vol. 436, p. 184 - 194]
[5]Wang, Wei; Feng, Xiu; Liu, Huan-Xiang; Chen, Shi-Wu; Hui, Ling [Bioorganic and Medicinal Chemistry, 2018, vol. 26, # 12, p. 3217 - 3226]
[6]Chen, Shi-Wu; Hao, Shu-Yi; Mou, Hong-Xia; Wang, Shuai; Xu, Yu; Zhang, Xiu-Juan [Bioorganic and Medicinal Chemistry Letters, 2020, vol. 30, # 23]

6
[ 85-44-9 ]
[ 3660-90-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: ethanol / 80 °C 2: phosphorus pentabromide / 1,2-dichloro-ethane / 48 h / Reflux
	Multi-step reaction with 2 steps 1: hydrazine; acetic acid / 120 °C 2: phosphorus(V) oxybromide / 1,2-dichloro-ethane / Reflux
	Multi-step reaction with 2 steps 1: acetic acid; hydrazine hydrate / Reflux 2: phosphorus(V) oxybromide / 1,2-dichloro-ethane / Reflux

Reference： [1]Prime, Michael E.; Courtney, Stephen M.; Brookfield, Frederick A.; Marston, Richard W.; Walker, Victoria; Warne, Justin; Boyd, Andrew E.; Kairies, Norman A.; Von Der Saal, Wolfgang; Limberg, Anja; Georges, Guy; Engh, Richard A.; Goller, Bernhard; Rueger, Petra; Rueth, Matthias [Journal of Medicinal Chemistry, 2011, vol. 54, # 1, p. 312 - 319]
[2]Wang, Wei; Feng, Xiu; Liu, Huan-Xiang; Chen, Shi-Wu; Hui, Ling [Bioorganic and Medicinal Chemistry, 2018, vol. 26, # 12, p. 3217 - 3226]
[3]Chen, Shi-Wu; Hao, Shu-Yi; Mou, Hong-Xia; Wang, Shuai; Xu, Yu; Zhang, Xiu-Juan [Bioorganic and Medicinal Chemistry Letters, 2020, vol. 30, # 23]

7
[ 3660-90-0 ]
[ 1402423-52-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 12 h / 90 °C 2: potassium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / water; 1,2-dimethoxyethane / 12 h / Inert atmosphere; Reflux
	Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 90 °C 2: sodium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / ethanol; water; toluene / 8 h / 80 °C / Inert atmosphere

Reference： [1]Gao, Rui; Liao, Sha; Zhang, Chen; Zhu, Weilong; Wang, Liyan; Huang, Jin; Zhao, Zhenjiang; Li, Honglin; Qian, Xuhong; Xu, Yufang [European Journal of Medicinal Chemistry, 2013, vol. 62, p. 597 - 604]
[2]Boshta, Nader M.; Bua, Silvia; Lee, Sang-Yong; Mirza, Salahuddin; Namasivayam, Vigneshwaran; Perotti, Arianna; Supuran, Claudiu T.; Müller, Christa E. [2021, vol. 12, # 7, p. 1187 - 1206]

8
[ 3660-90-0 ]
[ 1402423-44-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 12 h / 90 °C 2: sodium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / ethanol; water; toluene / 8 h / 80 °C / Inert atmosphere
	Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 90 °C 2: sodium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / ethanol; water; toluene / 8 h / 80 °C / Inert atmosphere

Reference： [1]Gao, Rui; Liao, Sha; Zhang, Chen; Zhu, Weilong; Wang, Liyan; Huang, Jin; Zhao, Zhenjiang; Li, Honglin; Qian, Xuhong; Xu, Yufang [European Journal of Medicinal Chemistry, 2013, vol. 62, p. 597 - 604]
[2]Boshta, Nader M.; Bua, Silvia; Lee, Sang-Yong; Mirza, Salahuddin; Namasivayam, Vigneshwaran; Perotti, Arianna; Supuran, Claudiu T.; Müller, Christa E. [2021, vol. 12, # 7, p. 1187 - 1206]

9
[ 3660-90-0 ]
[ 63-74-1 ]
[ 1402423-55-5 ]

Yield	Reaction Conditions	Operation in experiment
20%	With potassium carbonate In N,N-dimethyl-formamide at 90℃; for 12h;	4.1.2. Synthesis of 4-((4-bromophthalazin-1-yl)aminobenzenesulfonamide (3) To a mixture of 1,4-dibromophthalazine (286 mg, 1.0 mmol) and 4-aminobenzenesulfonamide (172 mg, 1.0 mmol) in DMF (10 mL) was added potassium carbonate (276 mg, 2.0 mmol). The reaction was heated at 90 °C overnight. The reaction mixture was distilled under reduced pressure to remove most of the DMF, and the remaining residue was partitioned between CH2Cl2 (250 mL) and saturated ammonium chloride solution (50 mL). The water layer was extracted with CH2Cl2 (2 × 100 mL). The combined organic layers were washed with brine (50 mL), dried over MgSO4, and evaporated under reduced pressure. Purification was performed by flash chromatography on silica gel (CH2Cl2) to give the title compound as a yellow crystal. Yield: 20%, 1H NMR (400 MHz, DMSO-d6) δ (ppm): 12.83 (s, 1H), 8.35 (d, J = 8.0 Hz, 1H), 8.10-8.05 (m, 1H), 8.00-7.95 (m, 2H), 7.67 (d, J = 8.8 Hz, 2H), 6.60 (d, J = 8.8 Hz, 2H), 5.93 (s, 2H). LC-MS (ESI): C14H12BrN4O2S calc. 379.9, found 380.0.
	With potassium carbonate In N,N-dimethyl-formamide at 90℃;

Reference： [1]Gao, Rui; Liao, Sha; Zhang, Chen; Zhu, Weilong; Wang, Liyan; Huang, Jin; Zhao, Zhenjiang; Li, Honglin; Qian, Xuhong; Xu, Yufang [European Journal of Medicinal Chemistry, 2013, vol. 62, p. 597 - 604]
[2]Boshta, Nader M.; Bua, Silvia; Lee, Sang-Yong; Mirza, Salahuddin; Namasivayam, Vigneshwaran; Perotti, Arianna; Supuran, Claudiu T.; Müller, Christa E. [2021, vol. 12, # 7, p. 1187 - 1206]

10
[ 3660-90-0 ]
[ 98-18-0 ]
[ 1402423-56-6 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate In N,N-dimethyl-formamide at 90℃; for 12h;

Reference： [1]Gao, Rui; Liao, Sha; Zhang, Chen; Zhu, Weilong; Wang, Liyan; Huang, Jin; Zhao, Zhenjiang; Li, Honglin; Qian, Xuhong; Xu, Yufang [European Journal of Medicinal Chemistry, 2013, vol. 62, p. 597 - 604]

11
[ 3660-90-0 ]
[ 106-50-3 ]
[ 1402423-58-8 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate In N,N-dimethyl-formamide at 90℃; for 12h;

Reference： [1]Gao, Rui; Liao, Sha; Zhang, Chen; Zhu, Weilong; Wang, Liyan; Huang, Jin; Zhao, Zhenjiang; Li, Honglin; Qian, Xuhong; Xu, Yufang [European Journal of Medicinal Chemistry, 2013, vol. 62, p. 597 - 604]

12
[ 3660-90-0 ]
[ 769-92-6 ]
[ 1402423-59-9 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate In N,N-dimethyl-formamide at 90℃; for 12h;

Reference： [1]Gao, Rui; Liao, Sha; Zhang, Chen; Zhu, Weilong; Wang, Liyan; Huang, Jin; Zhao, Zhenjiang; Li, Honglin; Qian, Xuhong; Xu, Yufang [European Journal of Medicinal Chemistry, 2013, vol. 62, p. 597 - 604]

13
2-(2-methyl-1,3-dioxolan-2-yl)-6-tributylstannyl-pyridine [ No CAS ]
[ 3660-90-0 ]
C₂₂H₁₆N₄O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; copper(I) bromide In toluene at 100℃; for 72h; Inert atmosphere; Schlenk technique;	Synthesis of 1,4-{(O=CMe)C₅H₃N}₂C₈H₄N₂ An oven-dried Schlenk flask equipped with a magnetic stir bar was evacuated and backfilled with nitrogen. The flask was charged with 1,4-dibromophthalazine (1.30g, 4.52mmol), 6-tributylstannyl-2-(2-methyl-1,3-dioxolan-2-yl)pyridine (4.51g, 9.94mmol, 2.2 eq.), tetrakis(triphenylphosphine)palladium(0) (0.42g, 0.36mmol, 0.08 eq.), cuprous bromide (0.104g, 0.72mmol, 0.16 eq.) and toluene (50mL). The reaction mixture was stirred and heated to 100°C for 72h. After removal of the solvent under reduced pressure, the resulting oil was stirred for 12h in 4M HCl (50mL). On cooling to room temperature, the reaction mixture was neutralised with sodium hydrogen carbonate and extracted with chloroform (3×40mL). The combined organic extracts washed with water (3×40mL), a saturated solution of the disodium salt of EDTA (2×30mL) and brine (1×50mL) and then dried over magnesium sulfate. Following filtration, the solvent was removed under reduced pressure and the crude product crystallised from ethanol at -30°C to give 1,4-{(O=CMe)2C5H4N2}2C8H4N2 as a pale yellow solid (72%, 1.21g). Mp: 167-169°C. 1H NMR (300MHz, CDCl3, 298K): δ 2.81 (s, 6H, C(O)CH3), 7.99 (dd, J(HH) 7.2, 3.3, 2H, phth-H), 8.15 (t, J(HH) 7.5, 2H, Py-H), 8.25 (d, J(HH) 7.5, 2H, Py-H), 8.55 (d, J(HH) 7.5, 2H, Py-H), 8.98 (dd, J(HH) 7.2, 3.3, 2H, phth-H). 13C{1H} NMR (75MHz, CDCl3, 298K): δ 24.9 (C(O)CH3), 120.9 (Py-CH/phth-CH), 125.2 (phth-C), 125.9 (Py-CH/phth-CH), 128.1 (Py-CH/phth-CH), 131.4 (Py-CH/phth-CH), 137.3 (Py-CH/phth-CH), 151.5 (Py-CN/phth-CN), 154.2 (Py-CN/phth-CN), 155.2 (Py-CN/phth-CN), 198.6 (C(O)CH3). IR (cm-1) 2941 (w), 1708 (s, C=O), 1583 (s, C=Npy), 1451 (w), 1376 (s), 1353 (s), 1294 (m), 1239 (m), 1214 (m), 1154 (w), 1075 (s), 1025 (s), 993 (s), 818 (s), 768(m), 750 (w), 733 (s), 694 (m), 678 (m). FABMS: m/z 369 [M]+. HRMS (FAB): calcd for C22H17N6O2 [M]+ 369.13515, found 369.13521.

Reference： [1]Savjani, Nicky; Singh, Kuldip; Solan, Gregory A. [Inorganica Chimica Acta, 2015, vol. 436, p. 184 - 194]

14
[ 3660-90-0 ]
[ 1227040-87-0 ]
C₆₀H₄₂N₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In ethanol; water; toluene at 80℃; Schlenk technique;

Reference： [1]Tang, Ruizhi; Wang, Xinyang; Zhang, Wanzheng; Zhuang, Xiaodong; Bi, Shuai; Zhang, Wenbei; Zhang, Fan [Journal of Materials Chemistry C, 2016, vol. 4, # 32, p. 7640 - 7648]

15
[ 3660-90-0 ]
[ 109-77-3 ]
C₁₄H₄N₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
20%	Stage #1: 1,4-dibromophthalazine; malononitrile With bis-triphenylphosphine-palladium(II) chloride; sodium hydride In tetrahydrofuran; mineral oil for 48h; Reflux; Inert atmosphere; Stage #2: With hydrogenchloride; lead dioxide In ethanol; water; benzene at 20℃; for 0.333333h;	1.2 2) PD-1 synthesis Reactant 1 (5.00 g, 17.4 mmol) was added to a 250 ml two-necked round flask, malononitrile (5.75 g, 87.0 mmol), sodium hydride (60%, oil suspension, 4.39 g, 182.7 mmol) and Pd (PPh3) 2Cl2 (25 mol%) were dissolved in dry THF and refluxed at a high temperature for 48 hours under nitrogen. The reaction mixture is poured into distilled water, washed with methylene chloride, acidified with 5% aqueous hydrochloric acid, and extracted with methylene chloride. After washing the extracted solution with brine, decompress the solvent. The contents were dissolved in an aqueous solution of benzene, ethanol and 5% hydrochloric acid, and then PbO2 (25 mol%) was added thereto, followed by stirring at room temperature for 20 minutes. Extraction with Methylene Chloride afforded the final compound with a yield of 20%

Reference： [1]Current Patent Assignee: LG DISPLAY CO.,LTD. - KR2017/79353, 2017, A Location in patent: Paragraph 0256; 0260-0262

16
[ 3660-90-0 ]
4-(cyanomethyl)-2,3,5,6-tetrahydrofluorobenzonitrile [ No CAS ]
C₂₆H₄F₈N₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
25%	Stage #1: 1,4-dibromophthalazine; 4-(cyanomethyl)-2,3,5,6-tetrahydrofluorobenzonitrile With bis-triphenylphosphine-palladium(II) chloride; sodium hydride In tetrahydrofuran; mineral oil for 48h; Reflux; Inert atmosphere; Stage #2: With hydrogenchloride; lead dioxide In ethanol; water; benzene at 20℃; for 0.333333h;	3 Synthesis Example 3: Synthesis of PD-3 Reactant 1 (5.00 g, 17.4 mmol) was added to a 250 ml two-necked round flask, Reactant 2 (18.6 g, 87.0 mmol), sodium hydride (60%, oil suspension, 4.39 g, 182.7 mmol) and Pd (PPh3) 2Cl2 (25 mol%) were dissolved in dry THF and refluxed at a high temperature for 48 hours under nitrogen. The reaction mixture was poured into distilled water, washed with methylene chloride, acidified with 5% aqueous hydrochloric acid, and extracted with methylene chloride. The extracted solution was washed with brine, and the solvent was reduced in pressure. The contents were dissolved in an aqueous solution of benzene, ethanol and 5% hydrochloric acid, and then PbO2 (25 mol%) was added thereto, followed by stirring at room temperature for 20 minutes. And extracted with methylene chloride to give the final compound with a yield of 25%.

Reference： [1]Current Patent Assignee: LG DISPLAY CO.,LTD. - KR2017/79353, 2017, A Location in patent: Paragraph 0271-0273

17
[ 3660-90-0 ]
1-(4-chlorophenyl)-3-(4-(4-(1-methyl-1H-pyrazol-4-yl)-1-oxophthalazin-2(1H)-yl)phenyl)urea [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1.1: acetic acid / Reflux 2.1: sodium hydride / N,N-dimethyl-formamide / 2 h / 20 °C 2.2: 20 h 3.1: sodium carbonate; palladium bis[bis(diphenylphosphino)ferrocene] dichloride / 1,4-dioxane / 12 h / Reflux; Inert atmosphere 4.1: iron; ammonium chloride / ethanol; water / 2 h / Reflux 5.1: dichloromethane / 24 h / 20 °C

Reference： [1]Chen, Shi-Wu; Hao, Shu-Yi; Mou, Hong-Xia; Wang, Shuai; Xu, Yu; Zhang, Xiu-Juan [Bioorganic and Medicinal Chemistry Letters, 2020, vol. 30, # 23]

18
[ 3660-90-0 ]
1-(2,4-difluorophenyl)-3-(4-(4-(1-methyl-1H-pyrazol-4-yl)-1-oxophthalazin-2(1H)-yl)phenyl)urea [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1.1: acetic acid / Reflux 2.1: sodium hydride / N,N-dimethyl-formamide / 2 h / 20 °C 2.2: 20 h 3.1: sodium carbonate; palladium bis[bis(diphenylphosphino)ferrocene] dichloride / 1,4-dioxane / 12 h / Reflux; Inert atmosphere 4.1: iron; ammonium chloride / ethanol; water / 2 h / Reflux 5.1: dichloromethane / 24 h / 20 °C

Reference： [1]Chen, Shi-Wu; Hao, Shu-Yi; Mou, Hong-Xia; Wang, Shuai; Xu, Yu; Zhang, Xiu-Juan [Bioorganic and Medicinal Chemistry Letters, 2020, vol. 30, # 23]

19
[ 3660-90-0 ]
[ 1402423-58-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: triethylamine / ethanol / 48 h / 65 °C 2: trifluoroacetic acid / dichloromethane / 1 h

Reference： [1]Chen, Shi-Wu; Hao, Shu-Yi; Mou, Hong-Xia; Wang, Shuai; Xu, Yu; Zhang, Xiu-Juan [Bioorganic and Medicinal Chemistry Letters, 2020, vol. 30, # 23]

20
[ 3660-90-0 ]
1-(4-((4-bromophthalazin-1-yl)amino)phenyl)-3-(4-chloro-3-(trifluoromethyl)phenyl)urea [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: triethylamine / ethanol / 48 h / 65 °C 2: trifluoroacetic acid / dichloromethane / 1 h 3: dichloromethane / 24 h / 20 °C

Reference： [1]Chen, Shi-Wu; Hao, Shu-Yi; Mou, Hong-Xia; Wang, Shuai; Xu, Yu; Zhang, Xiu-Juan [Bioorganic and Medicinal Chemistry Letters, 2020, vol. 30, # 23]

21
[ 3660-90-0 ]
1-(4-((4-bromophthalazin-1-yl)amino)phenyl)-3-(3-(trifluoromethyl)phenyl)urea [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: triethylamine / ethanol / 48 h / 65 °C 2: trifluoroacetic acid / dichloromethane / 1 h 3: dichloromethane / 24 h / 20 °C

Reference： [1]Chen, Shi-Wu; Hao, Shu-Yi; Mou, Hong-Xia; Wang, Shuai; Xu, Yu; Zhang, Xiu-Juan [Bioorganic and Medicinal Chemistry Letters, 2020, vol. 30, # 23]

22
[ 3660-90-0 ]
1-(4-chloro-3-(trifluoromethyl)phenyl)-3-(4-((4-oxo-3,4-dihydrophthalazin-1-yl) amino)phenyl)urea [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: triethylamine / ethanol / 48 h / 65 °C 2: trifluoroacetic acid / dichloromethane / 1 h 3: dichloromethane / 24 h / 20 °C 4: sodium acetate; acetic acid / 2 h / Reflux

Reference： [1]Chen, Shi-Wu; Hao, Shu-Yi; Mou, Hong-Xia; Wang, Shuai; Xu, Yu; Zhang, Xiu-Juan [Bioorganic and Medicinal Chemistry Letters, 2020, vol. 30, # 23]

23
[ 3660-90-0 ]
1-(4-((4-oxo-3,4-dihydrophthalazin-1-yl)amino)phenyl)-3-(3-(trifluoromethyl)phenyl) urea [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: triethylamine / ethanol / 48 h / 65 °C 2: trifluoroacetic acid / dichloromethane / 1 h 3: dichloromethane / 24 h / 20 °C 4: sodium acetate; acetic acid / 2 h / Reflux

Reference： [1]Chen, Shi-Wu; Hao, Shu-Yi; Mou, Hong-Xia; Wang, Shuai; Xu, Yu; Zhang, Xiu-Juan [Bioorganic and Medicinal Chemistry Letters, 2020, vol. 30, # 23]

24
[ 3660-90-0 ]
4-((4-nitrobenzyl)amino)phthalazin-1(2H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: triethylamine / ethanol / 48 h / 65 °C 2: sodium acetate; acetic acid / 2 h / Reflux

Reference： [1]Chen, Shi-Wu; Hao, Shu-Yi; Mou, Hong-Xia; Wang, Shuai; Xu, Yu; Zhang, Xiu-Juan [Bioorganic and Medicinal Chemistry Letters, 2020, vol. 30, # 23]

25
[ 3660-90-0 ]
4-((4-nitrophenethyl)amino)phthalazin-1(2H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: triethylamine / ethanol / 48 h / 65 °C 2: anhydrous Sodium acetate; glacial acetic acid / 2 h / Reflux
	Multi-step reaction with 2 steps 1: anhydrous sodium carbonate / ethanol / 72 h / 65 °C 2: glacial acetic acid / 2 h / 120 °C

Reference： [1]Chen, Shi-Wu; Hao, Shu-Yi; Mou, Hong-Xia; Wang, Shuai; Xu, Yu; Zhang, Xiu-Juan [Bioorganic and Medicinal Chemistry Letters, 2020, vol. 30, # 23]
[2]Current Patent Assignee: LANZHOU UNIVERSITY - CN113773263, 2021, A

26
[ 3660-90-0 ]
4-((4-aminobenzyl)amino)phthalazin-1(2H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: triethylamine / ethanol / 48 h / 65 °C 2: sodium acetate; acetic acid / 2 h / Reflux 3: iron; ammonium chloride / ethanol; water / 2 h / Reflux

Reference： [1]Chen, Shi-Wu; Hao, Shu-Yi; Mou, Hong-Xia; Wang, Shuai; Xu, Yu; Zhang, Xiu-Juan [Bioorganic and Medicinal Chemistry Letters, 2020, vol. 30, # 23]

27
[ 3660-90-0 ]
4-((4-aminophenethyl)amino)phthalazin-1(2H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: triethylamine / ethanol / 48 h / 65 °C 2: anhydrous Sodium acetate; glacial acetic acid / 2 h / Reflux 3: iron⁽⁰⁾; ammonia hydrochloride / ethanol; lithium hydroxide monohydrate / 2 h / Reflux
	Multi-step reaction with 3 steps 1: anhydrous sodium carbonate / ethanol / 72 h / 65 °C 2: glacial acetic acid / 2 h / 120 °C 3: iron⁽⁰⁾; ammonia hydrochloride; ethanol; lithium hydroxide monohydrate / 2 h / Reflux

Reference： [1]Chen, Shi-Wu; Hao, Shu-Yi; Mou, Hong-Xia; Wang, Shuai; Xu, Yu; Zhang, Xiu-Juan [Bioorganic and Medicinal Chemistry Letters, 2020, vol. 30, # 23]
[2]Current Patent Assignee: LANZHOU UNIVERSITY - CN113773263, 2021, A

28
[ 3660-90-0 ]
1-(4-chloro-3-(trifluoromethyl)phenyl)-3-(4-(((4-oxo-3,4-dihydrophthalazin-1-yl)amino)methyl)phenyl)urea [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: triethylamine / ethanol / 48 h / 65 °C 2: sodium acetate; acetic acid / 2 h / Reflux 3: iron; ammonium chloride / ethanol; water / 2 h / Reflux 4: dichloromethane / 24 h / 20 °C

Reference： [1]Chen, Shi-Wu; Hao, Shu-Yi; Mou, Hong-Xia; Wang, Shuai; Xu, Yu; Zhang, Xiu-Juan [Bioorganic and Medicinal Chemistry Letters, 2020, vol. 30, # 23]

29
[ 3660-90-0 ]
C₂₃H₁₈F₃N₅O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: triethylamine / ethanol / 48 h / 65 °C 2: sodium acetate; acetic acid / 2 h / Reflux 3: iron; ammonium chloride / ethanol; water / 2 h / Reflux 4: dichloromethane / 24 h / 20 °C

Reference： [1]Chen, Shi-Wu; Hao, Shu-Yi; Mou, Hong-Xia; Wang, Shuai; Xu, Yu; Zhang, Xiu-Juan [Bioorganic and Medicinal Chemistry Letters, 2020, vol. 30, # 23]

30
[ 3660-90-0 ]
1-(4-chloro-3-(trifluoromethyl)phenyl)-3-(4-(2-((4-oxo-3,4-dihydrophthalazin-1-yl)amino)ethyl)phenyl)urea [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: triethylamine / ethanol / 48 h / 65 °C 2: sodium acetate; acetic acid / 2 h / Reflux 3: iron; ammonium chloride / ethanol; water / 2 h / Reflux 4: dichloromethane / 24 h / 20 °C

Reference： [1]Chen, Shi-Wu; Hao, Shu-Yi; Mou, Hong-Xia; Wang, Shuai; Xu, Yu; Zhang, Xiu-Juan [Bioorganic and Medicinal Chemistry Letters, 2020, vol. 30, # 23]

31
[ 3660-90-0 ]
1-(4-(2-((4-oxo-3,4-dihydrophthalazin-1-yl)amino)ethyl)phenyl)-3-(3-(trifluoromethyl) phenyl)urea [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: triethylamine / ethanol / 48 h / 65 °C 2: anhydrous Sodium acetate; glacial acetic acid / 2 h / Reflux 3: iron⁽⁰⁾; ammonia hydrochloride / ethanol; lithium hydroxide monohydrate / 2 h / Reflux 4: dichloromethane / 24 h / 20 °C
	Multi-step reaction with 4 steps 1: anhydrous sodium carbonate / ethanol / 72 h / 65 °C 2: glacial acetic acid / 2 h / 120 °C 3: iron⁽⁰⁾; ammonia hydrochloride; ethanol; lithium hydroxide monohydrate / 2 h / Reflux 4: dichloromethane / 24 h / 20 °C

Reference： [1]Chen, Shi-Wu; Hao, Shu-Yi; Mou, Hong-Xia; Wang, Shuai; Xu, Yu; Zhang, Xiu-Juan [Bioorganic and Medicinal Chemistry Letters, 2020, vol. 30, # 23]
[2]Current Patent Assignee: LANZHOU UNIVERSITY - CN113773263, 2021, A

32
[ 3660-90-0 ]
1-(4-chlorophenyl)-3-(4-(2-((4-oxo-3,4-dihydrophthalazin-1-yl)amino)ethyl)phenyl)urea [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: triethylamine / ethanol / 48 h / 65 °C 2: anhydrous Sodium acetate; glacial acetic acid / 2 h / Reflux 3: iron⁽⁰⁾; ammonia hydrochloride / ethanol; lithium hydroxide monohydrate / 2 h / Reflux 4: dichloromethane / 24 h / 20 °C
	Multi-step reaction with 4 steps 1: anhydrous sodium carbonate / ethanol / 72 h / 65 °C 2: glacial acetic acid / 2 h / 120 °C 3: iron⁽⁰⁾; ammonia hydrochloride; ethanol; lithium hydroxide monohydrate / 2 h / Reflux 4: dichloromethane / 24 h / 20 °C

Reference： [1]Chen, Shi-Wu; Hao, Shu-Yi; Mou, Hong-Xia; Wang, Shuai; Xu, Yu; Zhang, Xiu-Juan [Bioorganic and Medicinal Chemistry Letters, 2020, vol. 30, # 23]
[2]Current Patent Assignee: LANZHOU UNIVERSITY - CN113773263, 2021, A

33
[ 3660-90-0 ]
1-cyclohexyl-3-(4-(2-((4-oxo-3,4-dihydrophthalazin-1-yl)amino)ethyl)phenyl)urea [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: triethylamine / ethanol / 48 h / 65 °C 2: anhydrous Sodium acetate; glacial acetic acid / 2 h / Reflux 3: iron⁽⁰⁾; ammonia hydrochloride / ethanol; lithium hydroxide monohydrate / 2 h / Reflux 4: dichloromethane / 24 h / 20 °C
	Multi-step reaction with 4 steps 1: anhydrous sodium carbonate / ethanol / 72 h / 65 °C 2: glacial acetic acid / 2 h / 120 °C 3: iron⁽⁰⁾; ammonia hydrochloride; ethanol; lithium hydroxide monohydrate / 2 h / Reflux 4: dichloromethane / 24 h / 20 °C

Reference： [1]Chen, Shi-Wu; Hao, Shu-Yi; Mou, Hong-Xia; Wang, Shuai; Xu, Yu; Zhang, Xiu-Juan [Bioorganic and Medicinal Chemistry Letters, 2020, vol. 30, # 23]
[2]Current Patent Assignee: LANZHOU UNIVERSITY - CN113773263, 2021, A

34
[ 3660-90-0 ]
4-chloro-N-(4-(2-((4-oxo-3,4-dihydrophthalazin-1-yl)amino)ethyl)phenyl)-3-(trifluoromethyl)benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: triethylamine / ethanol / 48 h / 65 °C 2: anhydrous Sodium acetate; glacial acetic acid / 2 h / Reflux 3: iron⁽⁰⁾; ammonia hydrochloride / ethanol; lithium hydroxide monohydrate / 2 h / Reflux 4: N-[3-(N,N-dimethylamino)-propyl]-N'-ethyl-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 12 h / 20 °C
	Multi-step reaction with 4 steps 1: anhydrous sodium carbonate / ethanol / 72 h / 65 °C 2: glacial acetic acid / 2 h / 120 °C 3: iron⁽⁰⁾; ammonia hydrochloride; ethanol; lithium hydroxide monohydrate / 2 h / Reflux 4: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 24 h / 20 °C

Reference： [1]Chen, Shi-Wu; Hao, Shu-Yi; Mou, Hong-Xia; Wang, Shuai; Xu, Yu; Zhang, Xiu-Juan [Bioorganic and Medicinal Chemistry Letters, 2020, vol. 30, # 23]
[2]Current Patent Assignee: LANZHOU UNIVERSITY - CN113773263, 2021, A

35
[ 3660-90-0 ]
N-(4-(2-((4-oxo-3,4-dihydrophthalazin-1-yl)amino)ethyl)phenyl)-3-(trifluoromethyl)benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: triethylamine / ethanol / 48 h / 65 °C 2: sodium acetate; acetic acid / 2 h / Reflux 3: iron; ammonium chloride / ethanol; water / 2 h / Reflux 4: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 12 h / 20 °C

Reference： [1]Chen, Shi-Wu; Hao, Shu-Yi; Mou, Hong-Xia; Wang, Shuai; Xu, Yu; Zhang, Xiu-Juan [Bioorganic and Medicinal Chemistry Letters, 2020, vol. 30, # 23]

36
[ 3660-90-0 ]
N-(4-(2-((4-oxo-3,4-dihydrophthalazin-1-yl)amino)ethyl)phenyl)-2-(3-(trifluoromethyl)phenyl)acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: triethylamine / ethanol / 48 h / 65 °C 2: sodium acetate; acetic acid / 2 h / Reflux 3: iron; ammonium chloride / ethanol; water / 2 h / Reflux 4: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 12 h / 20 °C

Reference： [1]Chen, Shi-Wu; Hao, Shu-Yi; Mou, Hong-Xia; Wang, Shuai; Xu, Yu; Zhang, Xiu-Juan [Bioorganic and Medicinal Chemistry Letters, 2020, vol. 30, # 23]

37
[ 3660-90-0 ]
2-cyclohexyl-N-(4-(2-((4-oxo-3,4-dihydrophthalazin-1-yl)amino)ethyl)phenyl)acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: triethylamine / ethanol / 48 h / 65 °C 2: sodium acetate; acetic acid / 2 h / Reflux 3: iron; ammonium chloride / ethanol; water / 2 h / Reflux 4: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 12 h / 20 °C

Reference： [1]Chen, Shi-Wu; Hao, Shu-Yi; Mou, Hong-Xia; Wang, Shuai; Xu, Yu; Zhang, Xiu-Juan [Bioorganic and Medicinal Chemistry Letters, 2020, vol. 30, # 23]

38
[ 3660-90-0 ]
N-(4-(2-((4-oxo-3,4-dihydrophthalazin-1-yl)amino)ethyl)phenyl)cyclohexanecarboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: triethylamine / ethanol / 48 h / 65 °C 2: sodium acetate; acetic acid / 2 h / Reflux 3: iron; ammonium chloride / ethanol; water / 2 h / Reflux 4: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 12 h / 20 °C

Reference： [1]Chen, Shi-Wu; Hao, Shu-Yi; Mou, Hong-Xia; Wang, Shuai; Xu, Yu; Zhang, Xiu-Juan [Bioorganic and Medicinal Chemistry Letters, 2020, vol. 30, # 23]

39
[ 3660-90-0 ]
4-bromo-2-(4-nitrophenyl)phthalazin-1(2H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: acetic acid / Reflux 2.1: sodium hydride / N,N-dimethyl-formamide / 2 h / 20 °C 2.2: 20 h

Reference： [1]Chen, Shi-Wu; Hao, Shu-Yi; Mou, Hong-Xia; Wang, Shuai; Xu, Yu; Zhang, Xiu-Juan [Bioorganic and Medicinal Chemistry Letters, 2020, vol. 30, # 23]

40
[ 3660-90-0 ]
4-(1-methyl-1H-pyrazol-4-yl)-2-(4-nitrophenyl)phthalazin-1(2H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: acetic acid / Reflux 2.1: sodium hydride / N,N-dimethyl-formamide / 2 h / 20 °C 2.2: 20 h 3.1: sodium carbonate; palladium bis[bis(diphenylphosphino)ferrocene] dichloride / 1,4-dioxane / 12 h / Reflux; Inert atmosphere

Reference： [1]Chen, Shi-Wu; Hao, Shu-Yi; Mou, Hong-Xia; Wang, Shuai; Xu, Yu; Zhang, Xiu-Juan [Bioorganic and Medicinal Chemistry Letters, 2020, vol. 30, # 23]

41
[ 3660-90-0 ]
2-(4-aminophenyl)-4-(1-methyl-1H-pyrazol-4-yl)phthalazin-1(2H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: acetic acid / Reflux 2.1: sodium hydride / N,N-dimethyl-formamide / 2 h / 20 °C 2.2: 20 h 3.1: sodium carbonate; palladium bis[bis(diphenylphosphino)ferrocene] dichloride / 1,4-dioxane / 12 h / Reflux; Inert atmosphere 4.1: iron; ammonium chloride / ethanol; water / 2 h / Reflux

Reference： [1]Chen, Shi-Wu; Hao, Shu-Yi; Mou, Hong-Xia; Wang, Shuai; Xu, Yu; Zhang, Xiu-Juan [Bioorganic and Medicinal Chemistry Letters, 2020, vol. 30, # 23]

42
[ 3660-90-0 ]
1-(4-chloro-3-(trifluoromethyl)phenyl)-3-(4-(4-(1-methyl-1H-pyrazol-4-yl)-1-oxophthalazin-2(1H)-yl)phenyl)urea [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1.1: acetic acid / Reflux 2.1: sodium hydride / N,N-dimethyl-formamide / 2 h / 20 °C 2.2: 20 h 3.1: sodium carbonate; palladium bis[bis(diphenylphosphino)ferrocene] dichloride / 1,4-dioxane / 12 h / Reflux; Inert atmosphere 4.1: iron; ammonium chloride / ethanol; water / 2 h / Reflux 5.1: dichloromethane / 24 h / 20 °C

Reference： [1]Chen, Shi-Wu; Hao, Shu-Yi; Mou, Hong-Xia; Wang, Shuai; Xu, Yu; Zhang, Xiu-Juan [Bioorganic and Medicinal Chemistry Letters, 2020, vol. 30, # 23]

43
[ 3660-90-0 ]
1-(4-(4-(1-methyl-1H-pyrazol-4-yl)-1-oxophthalazin-2(1H)-yl)phenyl)-3-(3-(trifluoro methyl)phenyl)urea [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1.1: acetic acid / Reflux 2.1: sodium hydride / N,N-dimethyl-formamide / 2 h / 20 °C 2.2: 20 h 3.1: sodium carbonate; palladium bis[bis(diphenylphosphino)ferrocene] dichloride / 1,4-dioxane / 12 h / Reflux; Inert atmosphere 4.1: iron; ammonium chloride / ethanol; water / 2 h / Reflux 5.1: dichloromethane / 24 h / 20 °C

Reference： [1]Chen, Shi-Wu; Hao, Shu-Yi; Mou, Hong-Xia; Wang, Shuai; Xu, Yu; Zhang, Xiu-Juan [Bioorganic and Medicinal Chemistry Letters, 2020, vol. 30, # 23]

44
[ 3660-90-0 ]
[ 71026-66-9 ]
tert-butyl (4-((4-bromophthalazin-1-yl)amino)phenyl)carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
71%	With triethylamine In ethanol at 65℃; for 48h;	1.1.4. General procedures for preparation of compounds 8 and 11a-b General procedure: Triethylamine (2 mL, 14.43 mmol) was added to the mixture of 1,4-dibromoph- thalazine (1.73 g, 6.00 mmol) and appropriate amines (4.81 mmol) in ethanol (15 mL), and the resulting mixture was heated at 65°C for 48 h. Subsequently, the mixture was cooled to room temperature and poured into water (50 mL). Then, the insoluble matter was filtered, and the filter cake was dried. The crude product was purified by column chromatography (eluted with 00.5% methanol in DCM) to give compounds 8 and 11ab. 1.1.4.1. tert-Butyl (4-((4-bromophthalazin-1-yl)amino)phenyl)carbamate (8). Yield 71%; white solid; 1H NMR (600 MHz, DMSO-d6) δ 9.32 (s, 1H), 9.28 (d, J = 9.0 Hz, 1H), 8.61 (d, J = 7.8 Hz, 1H), 8.08 (s, 3H), 7.69 (d, J = 8.4 Hz, 2H), 7.45 (d, J = 6.6 Hz, 2H), 1.49 (s, 9H).

Reference： [1]Chen, Shi-Wu; Hao, Shu-Yi; Mou, Hong-Xia; Wang, Shuai; Xu, Yu; Zhang, Xiu-Juan [Bioorganic and Medicinal Chemistry Letters, 2020, vol. 30, # 23]

45
[ 3660-90-0 ]
[ 7409-30-5 ]
4-bromo-N-(4-nitrobenzyl)phthalazin-1-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	With triethylamine In ethanol at 65℃; for 48h;	1.1.4. General procedures for preparation of compounds 8 and 11a-b General procedure: Triethylamine (2 mL, 14.43 mmol) was added to the mixture of 1,4-dibromoph- thalazine (1.73 g, 6.00 mmol) and appropriate amines (4.81 mmol) in ethanol (15 mL), and the resulting mixture was heated at 65°C for 48 h. Subsequently, the mixture was cooled to room temperature and poured into water (50 mL). Then, the insoluble matter was filtered, and the filter cake was dried. The crude product was purified by column chromatography (eluted with 00.5% methanol in DCM) to give compounds 8 and 11ab.

Reference： [1]Chen, Shi-Wu; Hao, Shu-Yi; Mou, Hong-Xia; Wang, Shuai; Xu, Yu; Zhang, Xiu-Juan [Bioorganic and Medicinal Chemistry Letters, 2020, vol. 30, # 23]

46
[ 3660-90-0 ]
[ 24954-67-4 ]
4-bromo-N-(4-nitrophenethyl)phthalazin-1-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With triethylamine In ethanol at 65℃; for 48h;	1.1.4. General procedures for preparation of compounds 8 and 11a-b General procedure: Triethylamine (2 mL, 14.43 mmol) was added to the mixture of 1,4-dibromoph- thalazine (1.73 g, 6.00 mmol) and appropriate amines (4.81 mmol) in ethanol (15 mL), and the resulting mixture was heated at 65°C for 48 h. Subsequently, the mixture was cooled to room temperature and poured into water (50 mL). Then, the insoluble matter was filtered, and the filter cake was dried. The crude product was purified by column chromatography (eluted with 00.5% methanol in DCM) to give compounds 8 and 11ab.

Reference： [1]Chen, Shi-Wu; Hao, Shu-Yi; Mou, Hong-Xia; Wang, Shuai; Xu, Yu; Zhang, Xiu-Juan [Bioorganic and Medicinal Chemistry Letters, 2020, vol. 30, # 23]

47
[ 3660-90-0 ]
[ 118-10-5 ]
(ECin)<SUB>2</SUB>PHAL [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
79%	Stage #1: Cinchonin With sodium hydride In N,N-dimethyl-formamide at 25℃; for 0.166667h; Inert atmosphere; Stage #2: 1,4-dibromophthalazine In N,N-dimethyl-formamide at 65℃; for 72h; Inert atmosphere;

Reference： [1]Jiang, Xiaojian; Xu, Xi; Xu, Wei; Yu, Pei; Yeung, Ying-Yeung [Organic Letters, 2021, vol. 23, # 16, p. 6316 - 6320]

48
[ 3660-90-0 ]
(+)-cinchonine [ No CAS ]
(Cin)<SUB>2</SUB>PHAL [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	Stage #1: (+)-cinchonine With sodium hydride In N,N-dimethyl-formamide at 25℃; for 0.166667h; Inert atmosphere; Stage #2: 1,4-dibromophthalazine In N,N-dimethyl-formamide at 65℃; for 72h; Inert atmosphere;

Reference： [1]Jiang, Xiaojian; Xu, Xi; Xu, Wei; Yu, Pei; Yeung, Ying-Yeung [Organic Letters, 2021, vol. 23, # 16, p. 6316 - 6320]

49
[ 3660-90-0 ]
[ 53297-70-4 ]
4-[(4-bromophthalazin-1-yl)amino]-3-methylbenzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
48%	With potassium carbonate In N,N-dimethyl-formamide at 90℃;

Reference： [1]Boshta, Nader M.; Bua, Silvia; Lee, Sang-Yong; Mirza, Salahuddin; Namasivayam, Vigneshwaran; Perotti, Arianna; Supuran, Claudiu T.; Müller, Christa E. [2021, vol. 12, # 7, p. 1187 - 1206]

50
[ 3660-90-0 ]
[ 29968-78-3 ]
4-bromo-N-(4-nitrophenethyl)phthalazin-1-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With anhydrous sodium carbonate In ethanol at 65℃; for 72h;	1 Example 1: Preparation of 4-bromo-N-(4-nitrophenethyl)phthalazin-1-amine The raw material 1,4-dibromophthalazine (21.0mmol) was dissolved in dry ethanol (30mL), Na2CO3 (60mmol) was added, 4-nitrophenethylamine hydrochloride (16.5mmol) was added, and the reaction was carried out at 65°C After 3 days, after the reaction, ethanol was evaporated under reduced pressure, and 5.31 g of white solid was obtained by column chromatography. The product testing data are as follows:

Reference： [1]Current Patent Assignee: LANZHOU UNIVERSITY - CN113773263, 2021, A Location in patent: Paragraph 0019-0022

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
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CAS No. :	3660-90-0	MDL No. :	MFCD13659422
Formula :	C₈H₄Br₂N₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	CNGXORPRECUFGX-UHFFFAOYSA-N
M.W :	287.94	Pubchem ID :	59627392
Synonyms :

Num. heavy atoms :	12
Num. arom. heavy atoms :	10
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	54.94
TPSA :	25.78 Å²

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.46 cm/s

Log Po/w (iLOGP) :	2.36
Log Po/w (XLOGP3) :	3.66
Log Po/w (WLOGP) :	3.15
Log Po/w (MLOGP) :	3.13
Log Po/w (SILICOS-IT) :	3.29
Consensus Log Po/w :	3.12

[ CAS No. 3660-90-0 ] {[proInfo.proName]}

Quality Control of [ 3660-90-0 ]

Related Doc. of [ 3660-90-0 ]

Product Details of [ 3660-90-0 ]

Calculated chemistry of [ 3660-90-0 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 3660-90-0 ]

Application In Synthesis of [ 3660-90-0 ]

[ 3660-90-0 ] Synthesis Path-Upstream 1~3

[ 3660-90-0 ] Synthesis Path-Downstream 1~50

Related Parent Nucleus of
[ 3660-90-0 ]

Phthalazines

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

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Inquiry

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	0.0
Bioavailability Score :	0.55

Log S (ESOL) :	-4.55
Solubility :	0.00816 mg/ml ; 0.0000283 mol/l
Class :	Moderately soluble
Log S (Ali) :	-3.89
Solubility :	0.037 mg/ml ; 0.000129 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-5.03
Solubility :	0.00271 mg/ml ; 0.0000094 mol/l
Class :	Moderately soluble

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.0

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

[ CAS No. 3660-90-0 ] {[proInfo.proName]}

Quality Control of [ 3660-90-0 ]

Related Doc. of [ 3660-90-0 ]

Product Details of [ 3660-90-0 ]

Calculated chemistry of [ 3660-90-0 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 3660-90-0 ]

Application In Synthesis of [ 3660-90-0 ]

[ 3660-90-0 ] Synthesis Path-Upstream 1~3

[ 3660-90-0 ] Synthesis Path-Downstream 1~50

Related Parent Nucleus of [ 3660-90-0 ]

Phthalazines

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Parent Nucleus of
[ 3660-90-0 ]