[ CAS No. 14148-44-8 ] {[proInfo.proName]}

Name: 14148-44-8|N-Methylquinolin-8-amine|95%
Brand: Ambeed
SKU: A289647
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Quality Control of [ 14148-44-8 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 14148-44-8 ]

CAS No. :	14148-44-8	MDL No. :	MFCD08693107
Formula :	C₁₀H₁₀N₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	NVDZAZXIBALFGT-UHFFFAOYSA-N
M.W :	158.20	Pubchem ID :	12270074
Synonyms :

Safety of [ 14148-44-8 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313	UN#:
Hazard Statements:	H315-H319	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 14148-44-8 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 14148-44-8 ]

[ 14148-44-8 ] Synthesis Path-Downstream 1~43

1
[ 578-66-5 ]
[ 80-48-8 ]
[ 14148-44-8 ]

Reference： [1]Yasuye; Yasukawa [Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1946, vol. 66, p. 4][Chem.Abstr., 1951, p. 6204]

2
[ 148-24-3 ]
[ 74-89-5 ]
[ 14148-44-8 ]

Yield	Reaction Conditions	Operation in experiment
80%	With ammonium chloride In ethanol at 200℃; for 20h;

Reference： [1]Terenin, V. I.; Gerasimenko, V. A.; Nikishova, N. G.; Kurts, A. L.; Afanas'eva, T. A.; Bundel', Yu. G. [Journal of Organic Chemistry USSR (English Translation), 1990, vol. 26, # 10.2, p. 1890 - 1896][Zhurnal Organicheskoi Khimii, 1990, vol. 26, # 10, p. 2191 - 2198]

Yield	Reaction Conditions	Operation in experiment
	8-Hydroxychinolin (VI), Dimethylamin;
	8-Aminochinolin, CH3I;
	8-Formamidochinolin, LiAlH4;

8-Chinolinol, m. SO2 behandelte 33percentig. wss. Methylaminlsg. (3d, Kochen, pH 6);

4
[ 7647-01-0 ]
[ 578-66-5 ]
[ 14148-44-8 ]
[ 29526-42-9 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium bromide; calcium chloride; copper dichloride at 185℃;

Reference： [1]Yoshida [Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1947, vol. 67, p. 70][Chem.Abstr., 1951, p. 9544]

5
[ 14148-44-8 ]
[ 753-73-1 ]
8-methylaminoquinolinium tetrachlorodimethylstannate(IV) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
47%	In chloroform boiling equimolar amts. for 5 min; addn. of petroleum ether, crystn. (freezer, 1 h), recrystn. (MeOH/CHCl3=1:5);

Reference： [1]Hazell, Alan; Khoo, Lian Ee; Ouyang, Jiexiang; Rausch, Bernhard J.; Tavares, Zara Miravent [Acta Crystallographica, Section C: Crystal Structure Communications, 1998, vol. 54, # 6, p. 728 - 732]

6
[ 14148-44-8 ]
[ 1135-99-5 ]
8-methylaminoquinolinium tetrachlorodiphenylstannate(IV) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
46%	In chloroform boiling equimolar amts. for 5 min; addn. of petroleum ether, crystn. (freezer, 1 h), recrystn. (MeOH/CHCl3=1:5);

7
[ 578-66-5 ]
[ 13061-96-6 ]
[ 14148-44-8 ]

Yield	Reaction Conditions	Operation in experiment
30%	With pyridine; copper diacetate In 1,4-dioxane for 2h; Reflux;

Reference： [1]Gonzalez, Israel; Mosquera, Jesus; Guerrero, Cesar; Rodriguez, Ramon; Cruces, Jacobo [Organic Letters, 2009, vol. 11, # 8, p. 1677 - 1680]

8
[ 14148-44-8 ]
[ 75-24-1 ]
nickel dichloride [ No CAS ]
C₁₄H₂₁AlN₂Ni [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 8-(N-methylamino)quinoline; nickel dichloride In hexane Stage #2: trimethylaluminum In hexane for 0.5h;	1 To a stirring slurry of 1.30 g (0.01 mole) anhydrous NiCl2 in 50 mL of hexane, 1.58 g (0.01 mole) 8-(methylamino)quinoline is added in portions over a period of twenty minutes. The mixture is allowed to stir overnight and 50 mL (0.1 mole) of trimethyl aluminum (2.0 M in hexane) is added over a period of 30 minutes. The expected active component is: which is used “as is.”

Reference： [1]Current Patent Assignee: LYONDELLBASELL INDUSTRIES N.V. - US2005/70728, 2005, A1 Location in patent: Page/Page column 4

9
[ 578-66-5 ]
[ 14148-44-8 ]
[ 65198-16-5 ]

Yield	Reaction Conditions	Operation in experiment
1: 8% 2: 82%	Stage #1: 8-amino quinoline With sodium hydride; dimethyl sulfate In tetrahydrofuran at 75℃; for 24h; Inert atmosphere; Stage #2: With sodium hydroxide In tetrahydrofuran; water at 20℃; Inert atmosphere;

Reference： [1]Location in patent: experimental part Brancatelli, Giovanna; Drommi, Dario; Femino, Giusy; Saporita, Maria; Bottari, Giovanni; Faraone, Felice [New Journal of Chemistry, 2010, vol. 34, # 12, p. 2853 - 2860]

10
[ 14148-44-8 ]
[ 1028491-21-5 ]
C₃₆H₃₆N₆O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate

Reference： [1]Location in patent: scheme or table Stollenz, Michael; Gehring, Henrike; Konstanzer, Vera; Fischer, Stefan; Dechert, Sebastian; Grosse, Christian; Meyer, Franc [Organometallics, 2011, vol. 30, # 14, p. 3708 - 3725]

11
[ 14148-44-8 ]
[ 1028491-21-5 ]
[ 1192541-71-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: sodium carbonate 2: hydrogenchloride / ethanol

Reference： [1]Stollenz, Michael; Gehring, Henrike; Konstanzer, Vera; Fischer, Stefan; Dechert, Sebastian; Grosse, Christian; Meyer, Franc [Organometallics, 2011, vol. 30, # 14, p. 3708 - 3725]

12
[ 14148-44-8 ]
[ 3282-30-2 ]
[ 1429896-64-9 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine In dichloromethane at 20℃; for 6h; Inert atmosphere;

Reference： [1]Shang, Rui; Ilies, Laurean; Matsumoto, Arimasa; Nakamura, Eiichi [Journal of the American Chemical Society, 2013, vol. 135, # 16, p. 6030 - 6032,3]

13
[ 916314-51-7 ]
[ 74-89-5 ]
[ 14148-44-8 ]

Yield	Reaction Conditions	Operation in experiment
57%	With potassium phosphate; bis[chloro(1,2,3-trihapto-allylbenzene)palladium(II)]; N-[2-(di(1-adamantyl)phosphino)phenyl]morpholine In 1,4-dioxane; <i>tert</i>-butyl alcohol at 110℃; Inert atmosphere; Glovebox; chemoselective reaction;

Reference： [1]Alsabeh, Pamela G.; Stradiotto, Mark [Angewandte Chemie - International Edition, 2013, vol. 52, # 28, p. 7242 - 7246][Angew. Chem., 2013, vol. 125, # 28, p. 7383 - 7387]

14
[ 14148-44-8 ]
[ 1281554-27-5 ]
[ 1623481-94-6 ]

Yield	Reaction Conditions	Operation in experiment
	With N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In dichloromethane at 20℃; for 12h; Inert atmosphere;

Reference： [1]Gentry, Patrick R.; Kokubo, Masaya; Bridges, Thomas M.; Cho, Hyekyung P.; Smith, Emery; Chase, Peter; Hodder, Peter S.; Utley, Thomas J.; Rajapakse, Anuruddha; Byers, Frank; Niswender, Colleen M.; Morrison, Ryan D.; Daniels, J. Scott; Wood, Michael R.; Conn, P. Jeffrey; Lindsley, Craig W. [ChemMedChem, 2014, vol. 9, # 8, p. 1677 - 1682]

15
[ 14148-44-8 ]
[ 13918-92-8 ]
2,4-difluoro-N-methyl-N-(quinolin-8-yl)benzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
24%	With pyridine at 25℃; for 1h;

Reference： [1]Zhong, Fudi; Geng, Guannan; Chen, Bing; Pan, Ting; Li, Qianwen; Zhang, Hui; Bai, Chuan [Organic and Biomolecular Chemistry, 2015, vol. 13, # 6, p. 1792 - 1799]

16
[ 578-66-5 ]
[ 74-88-4 ]
[ 14148-44-8 ]

Yield	Reaction Conditions	Operation in experiment
67%	With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 24h;
62%	Stage #1: 8-amino quinoline With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: methyl iodide In N,N-dimethyl-formamide at 20℃; for 24h;
61%	In ethanol for 20h; Reflux;

61%	With potassium carbonate In N,N-dimethyl-formamide at 25℃;
60%	With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 24h;
31%	In ethanol at 0℃; for 20h; Reflux;
	With potassium carbonate In N,N-dimethyl-formamide at 55℃; for 24h; Sealed tube;

Reference： [1]Yan, Qi; Fang, Ye Chen; Jia, Yun Xue; Duan, Xin Hong [New Journal of Chemistry, 2017, vol. 41, # 6, p. 2372 - 2377]
[2]Kazi, Imran; Guha, Somraj; Sekar, Govindasamy [Journal of Organic Chemistry, 2019, vol. 84, # 11, p. 6642 - 6654]
[3]Zhong, Fudi; Geng, Guannan; Chen, Bing; Pan, Ting; Li, Qianwen; Zhang, Hui; Bai, Chuan [Organic and Biomolecular Chemistry, 2015, vol. 13, # 6, p. 1792 - 1799]
[4]Kumar, Vipin; Banert, Klaus; Ray, Devalina; Saha, Biswajit [Organic and Biomolecular Chemistry, 2019, vol. 17, # 48, p. 10245 - 10250]
[5]Zhu, Lifan; Guo, Hongyu; Feng, Xiujuan; Yamamoto, Yoshinori; Bao, Ming [Journal of Organic Chemistry, 2020, vol. 85, # 13, p. 8740 - 8748]
[6]Arockiam, Percia Beatrice; Guillemard, Lucas; Wencel-Delord, Joanna [Advanced Synthesis and Catalysis, 2017, vol. 359, # 15, p. 2571 - 2579]
[7]Cheng, Hanchao; Lam, Tsz-Lung; Liu, Yungen; Tang, Zhou; Che, Chi-Ming [Angewandte Chemie - International Edition, 2021, vol. 60, # 3, p. 1383 - 1389][Angew. Chem., 2021, vol. 133, # 3, p. 1403 - 1409,7]

17
[ 14148-44-8 ]
[ 98-59-9 ]
N-methyl-5-tosylquinolin-8-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With potassium carbonate; copper(I) bromide In 1,2-dichloro-ethane at 100℃; for 12h; Inert atmosphere; Sealed tube; regioselective reaction;

Reference： [1]Wei, Jun; Jiang, Jingxing; Xiao, Xinsheng; Lin, Dongen; Deng, Yuanfu; Ke, Zhuofeng; Jiang, Huanfeng; Zeng, Wei [Journal of Organic Chemistry, 2016, vol. 81, # 3, p. 946 - 955]

18
[ 14148-44-8 ]
[ 423-39-2 ]
N-methyl-5-(perfluorobutyl)quinolin-8-amine [ No CAS ]
N-methyl-5,7-bis(perfluorobutyl)quinolin-8-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 29% 2: 43%	With potassium carbonate In acetone at 20℃; for 20h; Sealed tube; Inert atmosphere; Irradiation;

Reference： [1]Arockiam, Percia Beatrice; Guillemard, Lucas; Wencel-Delord, Joanna [Advanced Synthesis and Catalysis, 2017, vol. 359, # 15, p. 2571 - 2579]

19
N,4-dimethyl-N-(quinolin-8-yl)benzenesulfonamide [ No CAS ]
[ 14148-44-8 ]

Yield	Reaction Conditions	Operation in experiment
71%	With trifluorormethanesulfonic acid In 1,2-dichloro-ethane at 25 - 90℃; for 70h; Inert atmosphere;

Reference： [1]Javorskis, Tomas; Orentas, Edvinas [Journal of Organic Chemistry, 2017, vol. 82, # 24, p. 13423 - 13439]

20
[ 37366-09-9 ]
[ 14148-44-8 ]
C₁₆H₁₆ClN₂Ru⁽¹⁺⁾ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68%	In methanol at 20℃; for 24h;

Reference： [1]Patra, Soumyadip; Awasthi, Mahendra K.; Rai, Rohit K.; Deka, Hemanta; Mobin, Shaikh M.; Singh, Sanjay K. [European Journal of Inorganic Chemistry, 2019, vol. 2019, # 7, p. 1046 - 1053]

21
[ 578-66-5 ]
[ 50-00-0 ]
[ 14148-44-8 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 8-amino quinoline; formaldehyd With sodium methylate In methanol for 4h; Reflux; Inert atmosphere; Stage #2: With sodium tetrahydroborate In methanol for 2h; Reflux; Inert atmosphere;

22
[ 14148-44-8 ]
[ 1576-35-8 ]
N-methyl-5-(p-tolylthio)quinolin-8-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
21%	With copper(l) iodide; sodium carbonate In para-xylene at 120℃; for 12h;

Reference： [1]Yu, Qing; Yang, Yiming; Wan, Jie-Ping; Liu, Yunyun [Journal of Organic Chemistry, 2018, vol. 83, # 18, p. 11385 - 11391]

23
[ 67-56-1 ]
[ 578-66-5 ]
[ 14148-44-8 ]

Yield	Reaction Conditions	Operation in experiment
94%	With potassium <i>tert</i>-butylate; C₄₉H₅₀Cl₂Ir₂N₅O⁽¹⁺⁾*F₆P^(1-) at 130℃; for 4h;
92%	With C₃₁H₃₀ClIrN₃O⁽¹⁺⁾*F₆P^(1-); potassium <i>tert</i>-butylate at 130℃; for 12h;
43%	With rhodium(III) chloride hydrate; potassium <i>tert</i>-butylate at 150℃; for 48h; Sealed tube; High pressure;

Reference： [1]Huang, Shuang; Hong, Xi; Cui, He-Zhen; Zhan, Bing; Li, Zhi-Ming; Hou, Xiu-Feng [Organometallics, 2020, vol. 39, # 19, p. 3514 - 3523]
[2]Huang, Shuang; Hong, Xi; Cui, He-Zhen; Zhou, Quan; Lin, Yue-Jian; Hou, Xiu-Feng [Dalton Transactions, 2019, vol. 48, # 15, p. 5072 - 5082]
[3]Sarki, Naina; Goyal, Vishakha; Tyagi, Nitin Kumar; Puttaswamy; Narani, Anand; Ray, Anjan; Natte, Kishore [ChemCatChem, 2021, vol. 13, # 7, p. 1722 - 1729]

24
[ 14148-44-8 ]
5-iodo-N-methylquinolin-8-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	With pyridine; tert.-butylhydroperoxide; iodine In decane; water at 20℃; for 3h; regioselective reaction;

Reference： [1]Kazi, Imran; Guha, Somraj; Sekar, Govindasamy [Journal of Organic Chemistry, 2019, vol. 84, # 11, p. 6642 - 6654]

25
[ 14148-44-8 ]
[ 98-88-4 ]
[ 14788-57-9 ]

Yield	Reaction Conditions	Operation in experiment
81%	With triethylamine In dichloromethane at 0 - 20℃;

Reference： [1]Kumar, Sandeep; Pradhan, Sourav; Roy, Subhasish; De, Pinaki Bhusan; Punniyamurthy, Tharmalingam [Journal of Organic Chemistry, 2019, vol. 84, # 16, p. 10481 - 10489]

26
[ 67-56-1 ]
[ 607-35-2 ]
[ 14148-44-8 ]

Yield	Reaction Conditions	Operation in experiment
	With palladium 10% on activated carbon; potassium <i>tert</i>-butylate at 130℃; for 20h;

Reference： [1]Goyal, Vishakha; Gahtori, Jyoti; Narani, Anand; Gupta, Piyush; Bordoloi, Ankur; Natte, Kishore [Journal of Organic Chemistry, 2019, vol. 84, # 23, p. 15389 - 15398]

27
[ 14148-44-8 ]
[ 1666-13-3 ]
N-methyl-5-(phenylselanyl)quinolin-8-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
50%	With tert.-butylhydroperoxide; iodine In acetonitrile at 50℃; for 0.5h; Green chemistry; regioselective reaction;

Reference： [1]Kumar, Vipin; Banert, Klaus; Ray, Devalina; Saha, Biswajit [Organic and Biomolecular Chemistry, 2019, vol. 17, # 48, p. 10245 - 10250]

28
[ 14148-44-8 ]
4-chloro-6-(chloromethyl)-2-ethylpyrimidine [ No CAS ]
N-((6-chloro-2-ethylpyrimidin-4-yl)methyl)-N-methylquinolin-8-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
67%	With potassium carbonate; potassium iodide In acetonitrile Reflux;	4.1.10 General procedure for the synthesis of 19a-c General procedure: A mixture of N-methylquinolin-8-amine (3mmol, 1.0eq.), 18a/b/c (1.2eq.), KI (0.1eq.) and K2CO3 (2.0eq.) in CH3CN (10mL) was stirred at reflux overnight. The reaction solution was evaporated to remove most of CH3CN. The residue was purified by silica gel column chromatography (dichloromethane/methanol/ammonium hydroxide=100/1/1) to give the desired product.4.1.10.1 N-((6-Chloro-2-ethylpyrimidin-4-yl)methyl)-N-methylquinolin-8-amine (19a) (0040) Compound 19a was obtained as a yellow oil (yield 67%). 1H NMR (400MHz, CDCl3) δ 8.74 (d, J=2.8Hz, 1H), 8.11 (d, J=8.0Hz, 1H), 7.61 (s, 1H), 7.46-7.34 (m, 3H), 7.11 (d, J=7.2Hz, 1H), 4.86 (s, 2H), 3.05 (s, 3H), 2.95 (q, J=7.6Hz, 2H), 1.36 (q, J=7.6Hz, 3H). 13C NMR (150MHz, CDCl3) δ 172.7, 171.9, 161.4, 148.3, 147.7, 142.3, 136.6, 129.9, 126.8, 121.1, 120.6, 117.2, 115.4, 61.7, 41.0, 32.6, 12.8. MS (ESI/APCI) m/z 312.8 [M+H]+.

Reference： [1]Hao, Yongjin; He, Sudan; Li, Zhanhui; Lin, Yu; Luo, Lusong; Ma, Haikuo; Wu, Shuwei; Xia, Kaijiang; Xu, Chen; Yang, Qing; Zhang, Xiaohu; Zheng, Jiyue; Zhu, Fang [Bioorganic Chemistry, 2020, vol. 99]

29
[ 14148-44-8 ]
4-chloro-6-(chloromethyl)-2-cyclopropylpyrimidine [ No CAS ]
N-((6-chloro-2-cyclopropylpyrimidin-4-yl)methyl)-N-methylquinolin-8-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
33%	With potassium carbonate; potassium iodide In acetonitrile Reflux;	4.1.10 General procedure for the synthesis of 19a-c General procedure: A mixture of N-methylquinolin-8-amine (3mmol, 1.0eq.), 18a/b/c (1.2eq.), KI (0.1eq.) and K2CO3 (2.0eq.) in CH3CN (10mL) was stirred at reflux overnight. The reaction solution was evaporated to remove most of CH3CN. The residue was purified by silica gel column chromatography (dichloromethane/methanol/ammonium hydroxide=100/1/1) to give the desired product.

30
[ 14148-44-8 ]
4-chloro-6-(chloromethyl)-2-(methylthio)pyrimidine [ No CAS ]
N-((6-chloro-2-(methylthio)pyrimidin-4-yl)methyl)-N-methylquinolin-8-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
25%	With potassium carbonate; potassium iodide In acetonitrile Reflux;	4.1.10 General procedure for the synthesis of 19a-c General procedure: A mixture of N-methylquinolin-8-amine (3mmol, 1.0eq.), 18a/b/c (1.2eq.), KI (0.1eq.) and K2CO3 (2.0eq.) in CH3CN (10mL) was stirred at reflux overnight. The reaction solution was evaporated to remove most of CH3CN. The residue was purified by silica gel column chromatography (dichloromethane/methanol/ammonium hydroxide=100/1/1) to give the desired product.

31
[ 14148-44-8 ]
[ 85878-85-9 ]
N-((6-chloro-2-methylpyrimidin-4-yl)methyl)-N-methylquinolin-8-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
98%	With potassium carbonate; potassium iodide In acetonitrile Reflux;	4.1.6 N-((6-Chloro-2-methylpyrimidin-4-yl)methyl)-N-methylquinolin-8-amine (10) A mixture of 9 (890mg, 5.0mmol), N-methylquinolin-8-amine (530mg, 3.4mmol), KI (56mg, 0.34mmol) and K2CO3 (925mg, 6.7mmol) in CH3CN (20mL) was stirred at reflux overnight. The reaction solution was evaporated to remove most of CH3CN. The residue was purified by silica gel column chromatography (dichloromethane/methanol=100/1) to give the desired product (1.04g, 98%) as a yellow oil. 1H NMR (400MHz, CDCl3) δ 8.75 (d, J=2.4Hz, 1H), 8.13 (d, J=8.4Hz, 1H), 7.67 (s, 1H), 7.48-7.34 (m, 3H), 7.14 (d, J=7.6Hz, 1H), 4.83 (s, 2H), 3.04 (s, 3H), 2.72 (s, 3H). 13C NMR (150MHz, CDCl3) δ 171.9, 168.4, 161.4, 148.1, 147.7, 142.0, 136.9, 129.9, 126.9, 121.2, 120.8, 117.1, 115.7, 61.7, 41.1, 25.9. MS (ESI/APCI) m/z 298.8 [M+H]+.

32
[ 14148-44-8 ]
5-fluoro-4-(fluoromethyl)-2-methyl-6-(4-methylpiperazin-1-yl)pyrimidine [ No CAS ]
N-((5-fluoro-2-methyl-6-(4-methylpiperazin-1-yl)pyrimidin-4-yl)methyl)-N-methylquinolin-8-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
13%	With 1,1,1-tri(hydroxymethyl)propane; potassium iodide In water Reflux;	4.1.34 N-((5-Fluoro-2-methyl-6-(4-methylpiperazin-1-yl)pyrimidin-4-yl)methyl)-N-methylquinolin-8-amine (52) A mixture of 51 (48mg, 0.2mmol), N-methylquinolin-8-amine (63mg, 0.4mmol), KI (6mg, 0.036mmol) and 2-ethyl-2-(hydroxymethyl)propane-1,3-diol (295mg, 2.2mmol) in water (1mL) was stirred at reflux overnight. The reaction mixture was diluted with saturated NaHCO3 (10mL) and extracted with dichloromethane (20mL×3). The combined organic layer was dried over Na2SO4, filtered and evaporated. The residue was purified by silica gel column chromatography (dichloromethane/methanol=50/1) to give the product (20mg, 13%) as a yellow oil. 1H NMR (400MHz, CDCl3) δ 8.88 (d, J=4.0Hz, 1H), 8.08 (d, J=8.0Hz, 1H), 7.44-7.29 (m, 3H), 7.01 (s, 1H), 4.95 (s, 2H), 3.67-3.48 (m, 4H), 3.06 (s, 3H), 2.47-2.32 (m,7H), 2.26 (s, 3H). 13C NMR (150MHz, CDCl3) δ 161.3 (d, J=8.6Hz), 151.4 (d, J=5.1Hz), 150.7 (d, J=15.6Hz), 148.8, 147.7, 143.9 (d, J=255.2Hz), 142.9, 136.4, 129.5, 126.4, 120.9, 120.8, 117.3, 55.0, 46.2, 46.0, 45.9, 40.9, 25.5 (d, J=1.8Hz). HRMS (ESI): calcd for C21H26FN6 [M+H]+ 381.2197, found 381.2182. Purity: 95.3%.

33
[ 14148-44-8 ]
4,5-dichloro-6-(chloromethyl)-2-methylpyrimidine [ No CAS ]
N-((5,6-dichloro-2-methylpyrimidin-4-yl)methyl)-N-methylquinolin-8-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%	With potassium carbonate; potassium iodide In acetonitrile for 2h; Reflux;	4.1.37 N-((5,6-Dichloro-2-methylpyrimidin-4-yl)methyl)-N-methylquinolin-8-amine (56) A mixture of 55 (53mg, 0.25mmol), N-methylquinolin-8-amine (40mg, 0.25mmol), KI (5mg, 0.03mmol) and K2CO3 (70mg, 0.50mmol) in CH3CN (10mL) was stirred at reflux for 2h. The reaction mixture was filtered and the filtrate was evaporated. The residue was purified by silica gel column chromatography (dichloromethane/methanol=100/1) to give the desired product (60mg, 72%) as a colorless oil. 1H NMR (400MHz, CDCl3) δ 8.75 (d, J=2.4Hz, 1H), 8.09 (d, J=7.6Hz, 1H), 7.46-7.39 (m, 1H), 7.39-7.32 (m, 2H), 7.16 (d, J=7.2Hz, 1H), 5.24 (s, 2H), 3.25 (s, 3H), 2.60 (s, 3H). 13C NMR (150MHz, CDCl3) δ 167.1, 165.3, 158.0, 148.1, 147.4, 142.1, 136.7, 129.7, 126.7, 125.0, 120.9, 120.4, 116.7, 58.4, 41.6, 25.4. MS (ESI/APCI) m/z 332.7 [M+H] +.

34
[ 14148-44-8 ]
tert-butyl 4-(6-(chloromethyl)-5-cyano-2-methylpyrimidin-4-yl)piperazine-1-carboxylate [ No CAS ]
tert-butyl 4-(5-cyano-2-methyl-6-((methyl(quinolin-8-yl)amino)methyl)pyrimidin-4-yl)piperazine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
24%	With potassium carbonate; potassium iodide In acetonitrile for 2h; Reflux;	4.1.42 tert-Butyl 4-(5-cyano-2-methyl-6-((methyl(quinolin-8-yl)amino)methyl)pyrimidin-4-yl)piperazine-1-carboxylate (62) A mixture of 61 (85mg, 0.24mmol), N-methylquinolin-8-amine (38mg, 0.24mmol), KI (5mg, 0.03mmol) and K2CO3 (70mg, 0.5mmol) in 10mL of MeCN was stirred at reflux for 2h. The reaction solution was cold to room temperature and filtered. The filtrate was concentrated. The resulting residue was purified by silica gel column chromatography (dichloromethane/methanol=100/1) to give the desired product (20mg, 24%) as a yellow oil. 1H NMR (400MHz, CDCl3) δ 8.82 (s, 1H), 8.10 (d, J=7.2Hz, 1H), 7.51-7.34 (m, 3H), 7.09 (s, 1H), 5.12 (s, 2H), 3.82 (s, 4H), 3.67-3.40 (m, 4H), 3.18 (s, 3H), 2.47 (s, 3H), 1.47 (s, 9H). MS (ESI/APCI) m/z 473.9 [M+H]+.

35
[ 14148-44-8 ]
[ 79-04-9 ]
2-chloro-N-methyl-N-(quinolin-8-yl)acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	With triethylamine In dichloromethane at 0℃; for 3h;

Reference： [1]Zhu, Lifan; Guo, Hongyu; Feng, Xiujuan; Yamamoto, Yoshinori; Bao, Ming [Journal of Organic Chemistry, 2020, vol. 85, # 13, p. 8740 - 8748]

36
[ 578-66-5 ]
[ 33513-42-7 ]
[ 14148-44-8 ]

Yield	Reaction Conditions	Operation in experiment
38%	With trimethylamine-borane; sodium hydride at 80℃; for 24h; Inert atmosphere;

Reference： [1]Meng, Jing; Wang, Yi-Feng; Wang, Zhijuan; Xia, Hui-Min; Xu, Ai-Qing; Zhang, Feng-Lian [Organic and biomolecular chemistry, 2020, vol. 18, # 26, p. 4922 - 4926]

37
[ 14148-44-8 ]
1,3-dimethyl-3,4-dihydro-1,10-phenanthrolin-2(1H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: triethylamine / dichloromethane / 20 °C 2: C₃₁H₃₀N₂OPt; caesium carbonate / acetonitrile / 10 h / 20 °C / Irradiation; Sealed tube; Inert atmosphere

Reference： [1]Cheng, Hanchao; Lam, Tsz-Lung; Liu, Yungen; Tang, Zhou; Che, Chi-Ming [Angewandte Chemie - International Edition, 2021, vol. 60, # 3, p. 1383 - 1389][Angew. Chem., 2021, vol. 133, # 3, p. 1403 - 1409,7]

38
[ 14148-44-8 ]
[ 920-46-7 ]
N-methyl-N-(quinolin-8-yl)methacrylamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine In dichloromethane at 20℃;

39
[ 14148-44-8 ]
[ 625-38-7 ]
N-methyl-N-(quinolin-8-yl)but-3-enamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
51%	With dmap; diisopropyl-carbodiimide In dichloromethane at 20℃; for 2.5h;

Reference： [1]Yang, Tao; Jiang, Yi; Luo, Yixin; Lim, Joel Jun Han; Lan, Yu; Koh, Ming Joo [Journal of the American Chemical Society, 2020, vol. 142, # 51, p. 21410 - 21419]

40
[ 14148-44-8 ]
[ 4857-04-9 ]
N-((1H-benzo[d]imidazol-2-yl)methyl)-N-methylquinolin-8-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	Stage #1: N-methylquinolin-8-amine; 2-chloromethyl-1H-benzimidazole With potassium iodide In ethanol at 80℃; for 8h; Inert atmosphere; Stage #2: With potassium hydroxide In ethanol at 20 - 80℃; for 3h; Inert atmosphere;

Reference： [1]Maji, Ankur; Gupta, Shivangi; Maji, Milan; Kundu, Sabuj [Journal of Organic Chemistry, 2022, vol. 87, # 13, p. 8351 - 8367]

41
[ 14148-44-8 ]
[ 4857-04-9 ]
C₁₈H₁₆Cl₂MnN₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: potassium iodide / ethanol / 8 h / 80 °C / Inert atmosphere 1.2: 3 h / 20 - 80 °C / Inert atmosphere 2.1: acetonitrile / 4 h / 20 °C / Inert atmosphere

Reference： [1]Maji, Ankur; Gupta, Shivangi; Maji, Milan; Kundu, Sabuj [Journal of Organic Chemistry, 2022, vol. 87, # 13, p. 8351 - 8367]

42
[ 14148-44-8 ]
[ 4760-35-4 ]
N-methyl-N-((1-methyl-1H-benzo[d]imidazol-2-yl)methyl)quinolin-8-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	Stage #1: N-methylquinolin-8-amine; 2-chloromethyl-1-methyl-1H-benzoimidazole With potassium iodide In ethanol at 80℃; for 8h; Inert atmosphere; Stage #2: With potassium hydroxide In ethanol at 20 - 80℃; for 3h; Inert atmosphere;

Reference： [1]Maji, Ankur; Gupta, Shivangi; Maji, Milan; Kundu, Sabuj [Journal of Organic Chemistry, 2022, vol. 87, # 13, p. 8351 - 8367]

43
[ 14148-44-8 ]
[ 4760-35-4 ]
C₁₉H₁₈Cl₂MnN₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: potassium iodide / ethanol / 8 h / 80 °C / Inert atmosphere 1.2: 3 h / 20 - 80 °C / Inert atmosphere 2.1: acetonitrile / 4 h / 20 °C / Inert atmosphere

Reference： [1]Maji, Ankur; Gupta, Shivangi; Maji, Milan; Kundu, Sabuj [Journal of Organic Chemistry, 2022, vol. 87, # 13, p. 8351 - 8367]

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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

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
{[ item.p_purity ]}	{[ item.pr_size ]}	{[ getRatePrice(item.pr_usd, 1,1) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]}	{[ getRatePrice(item.pr_usd, 1,1) ]}	Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate) ]}	{[ item.pr_usastock ]}	Inquiry -	{[ item.pr_chinastock ]}	Inquiry -

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. 14148-44-8 ] {[proInfo.proName]}

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[ 14148-44-8 ] Synthesis Path-Downstream 1~43

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

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