Name: 27431-62-5|N1,N1-Diethylbutane-1,4-diamine|97%
Brand: Ambeed
SKU: A831367
Rating: 92 (25 reviews)

1
[ 27431-62-5 ]
[ 39787-83-2 ]
2-methoxy-4-nitro-benzoic acid-(4-diethylamino-butylamide) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With benzene

Reference： [1]Clinton et al. [Journal of the American Chemical Society, 1957, vol. 79, p. 2290,2291]

2
[ 27431-62-5 ]
[ 720656-95-1 ]
7-chloro-1-(2-chloro-benzyl)-4-(4-diethylamino-butylamino)-quinolinium; chloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With ethanol Behandeln des gebildeten Hydrojodids mit wss.-aethanol.Natronlauge und Behandeln einer Loesung des danach isolierten Reaktionsprodukts in Isopropylalkohol mit Chlorwasserstoff enthaldendem Aethanol;

Reference： [1]Surrey et al. [Journal of the American Chemical Society, 1959, vol. 81, p. 2894,2895]

3
[ 27431-62-5 ]
[ 3397-62-4 ]
N²-(4-diethylamino-butyl)-[1,3,5]triazine-2,4,6-triyltriamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine

Reference： [1]Mosher; Whitmore [Journal of the American Chemical Society, 1945, vol. 67, p. 662]

5
[ 27431-62-5 ]
[ 75090-52-7 ]
[ 47147-43-3 ]

Reference： [1]Journal of the American Chemical Society,1946,vol. 68,p. 113,115

6
[ 27431-62-5 ]
[ 13676-02-3 ]
N,N-diethyl-N'-(6-methoxy-[2]quinolyl)-butanediyldiamine [ No CAS ]

Reference： [1]Zhurnal Obshchei Khimii,1937,vol. 7,p. 1896,1904
Chemisches Zentralblatt,1938,vol. 109,p. 3774

7
[ 27431-62-5 ]
[ 6622-28-2 ]
[ 3562-70-7 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium iodide; phenol

Reference： [1]Andersag [Chemische Berichte, 1948, vol. 81, p. 499,505] Steck et al. [Journal of the American Chemical Society, 1946, vol. 68, p. 380,383]

8
[ 27431-62-5 ]
[ 4295-04-9 ]
N,N-diethyl-N'-(6-methoxy-[4]quinolyl)-butanediyldiamine [ No CAS ]

Reference： [1]Zhurnal Obshchei Khimii,1937,vol. 7,p. 1896,1904
Chemisches Zentralblatt,1938,vol. 109,p. 3774

9
[ 27431-62-5 ]
[ 181950-47-0 ]
N,N-diethyl-N'-benzo[h]quinolin-4-yl-butanediyldiamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	at 165℃;

Reference： [1]Foster et al. [Journal of the American Chemical Society, 1946, vol. 68, p. 1327,1330]

10
[ 27431-62-5 ]
[ 500790-63-6 ]
N,N-diethyl-N'-(5-chloro-3-methyl-[4]quinolyl)-butanediyldiamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium iodide; phenol

Reference： [1]Steck et al. [Journal of the American Chemical Society, 1946, vol. 68, p. 380,383]

11
[ 27431-62-5 ]
[ 61773-04-4 ]
N,N-diethyl-N'-(2-methyl-benzo[h]quinolin-4-yl)-butanediyldiamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	at 200℃;

Reference： [1]Utermohlen; Hamilton [Journal of the American Chemical Society, 1941, vol. 63, p. 156,158]

12
[ 27431-62-5 ]
[ 61773-06-6 ]
N,N-diethyl-N'-(4-methyl-benzo[h]quinolin-2-yl)-butanediyldiamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	at 200℃;

Reference： [1]Utermohlen; Hamilton [Journal of the American Chemical Society, 1941, vol. 63, p. 156,158]

13
[ 5336-75-4 ]
[ 27431-62-5 ]

Yield	Reaction Conditions	Operation in experiment
	With ethanol; sodium durch Reduktion;
	With nickel at 105℃; Hydrogenation;
	With methanol; ammonia; nickel at 20℃; Hydrogenation;

	With ammonium hydroxide; nickel at 100℃; Hydrogenation;
	With ammonia; nickel Hydrogenation;
	With lithium aluminium tetrahydride; diethyl ether
	With ammonia; hydrogen In methanol
	With ethanol; sodium durch Reduktion;
		R.93.h Reference Example 93h Reference Example 93h 4-(diethylamino)-butylamine. Using 4-(diethylamino)-butanenitrile (reference example 94h) as substrate. MS (ion spray) m/z 145 (M+H)+.

Reference： [1]Utermohlen; Hamilton [Journal of the American Chemical Society, 1941, vol. 63, p. 156,158]
[2]Whitmore et al. [Journal of the American Chemical Society, 1944, vol. 66, p. 725,728]
[3]Huber [Journal of the American Chemical Society, 1944, vol. 66, p. 876,877]
[4]Grigorowskii; Weselitskaja [Zhurnal Obshchei Khimii, 1956, vol. 26, p. 466,468;engl.Ausg.S.491,492]
[5]Wadia et al. [Journal Of Scientific and Industrial Research, 1958, vol. 17B, p. 11,20][Chem.Abstr., 1958, p. 15547]
[6]Mizzoni et al. [Journal of the American Chemical Society, 1954, vol. 76, p. 2414,2417]
[7]Lespagnol,A. et al. [Bulletin de la Societe Chimique de France, 1960, p. 1162 - 1165]
[8]Strukow [1933, p. 333][Chemisches Zentralblatt, 1934, vol. 105, # II, p. 3494]
[9]Current Patent Assignee: SANOFI - US6541505, 2003, B1

14
[ 5336-75-4 ]
[ 27431-62-5 ]
[ 854392-77-1 ]

Yield	Reaction Conditions	Operation in experiment
	With methanol; ammonia; nickel Hydrogenation;
	With hydrogen In methanol for 60h; Title compound not separated from byproducts.;

Reference： [1]Huber [Journal of the American Chemical Society, 1944, vol. 66, p. 876,877]
[2]Park, Soobong; Hayes, Brittany L.; Marankan, Fatima; Mulhearn, Debbie C.; Wanna, Linda; Mesecar, Andrew D.; Santarsiero, Bernard D.; Johnson, Michael E.; Venton, Duane L. [Journal of Medicinal Chemistry, 2003, vol. 46, # 6, p. 936 - 953]

15
[ 27431-62-5 ]
[ 57450-55-2 ]
[ 19057-88-6 ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine

Reference： [1]Archer; Suter [Journal of the American Chemical Society, 1952, vol. 74, p. 4296,4301]

16
[ 27431-62-5 ]
[ 484640-62-2 ]
(7-methyl-2-oxo-2H-chromen-4-yl)-acetic acid-(4-diethylamino-butylamide) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With xylene

Reference： [1]Laskowski; Clinton [Journal of the American Chemical Society, 1950, vol. 72, p. 3987,3989]

17
[ 27431-62-5 ]
(7-ethyl-2-oxo-2H-chromen-4-yl)-acetic acid ethyl ester [ No CAS ]
(7-ethyl-2-oxo-2H-chromen-4-yl)-acetic acid-(4-diethylamino-butylamide) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With xylene

Reference： [1]Laskowski; Clinton [Journal of the American Chemical Society, 1950, vol. 72, p. 3987,3989]

18
[ 27431-62-5 ]
[ 32632-43-2 ]
(7-methoxy-2-oxo-2H-chromen-4-yl)-acetic acid-(4-diethylamino-butylamide) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With xylene

Reference： [1]Laskowski; Clinton [Journal of the American Chemical Society, 1950, vol. 72, p. 3987,3989]

19
[ 27431-62-5 ]
[ 88-73-3 ]
N-(4-diethylamino-butyl)-o-phenylenediamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	at 160℃; Hydrieren des Reaktionsprodukts an Platin in Methanol;

Reference： [1]Adams; Weisel; Mosher [Journal of the American Chemical Society, 1946, vol. 68, p. 883,886]

20
[ 27431-62-5 ]
[ 4355-31-1 ]
[ 101725-23-9 ]

Reference： [1]Gazzetta Chimica Italiana,1959,vol. 89,p. 1164,1175

21
[ 27431-62-5 ]
[ 85-42-7 ]
[ 93143-96-5 ]

Yield	Reaction Conditions	Operation in experiment
	at 170℃;

Reference： [1]Rice et al. [Journal of the American Chemical Society, 1953, vol. 75, p. 4911,4914]

22
1,1-Diethyl-1,2,3,6-tetrahydro-pyridazin-1-ium; bromide [ No CAS ]
[ 27431-62-5 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogen In methanol

Reference： [1]Zelenin,K.N.; Bezhan,I.P. [Journal of Organic Chemistry USSR (English Translation), 1970, vol. 6, p. 2216 - 2222][Zhurnal Organicheskoi Khimii, 1970, vol. 6, p. 2206 - 2214]

23
[ 27431-62-5 ]
[ 53966-34-0 ]
[ 80092-55-3 ]

Yield	Reaction Conditions	Operation in experiment
40%	In ethanol for 1.5h; Heating;

Reference： [1]Kesten, Stephen J.; Degnan, Margaret J.; Hung, Jocelyn; McNamara, Dennis J.; Ortwine, Daniel F.; et al. [Journal of Medicinal Chemistry, 1992, vol. 35, # 19, p. 3429 - 3447]

24
[ 27431-62-5 ]
[ 37597-30-1 ]
[ 104839-81-8 ]

Yield	Reaction Conditions	Operation in experiment
91%	In 1,2-dichloro-ethane at 20℃; for 18h;

Reference： [1]Arendaruk, A. P.; Abramova, N. A.; Skoldinov, A. P.; Kharkevich, D. A. [Pharmaceutical Chemistry Journal, 1986, vol. 20, # 7, p. 464 - 467][Khimiko-Farmatsevticheskii Zhurnal, 1986, vol. 20, # 7, p. 802 - 806]

25
[ 27431-62-5 ]
[ 97267-61-3 ]
7-bromo-N-(4'-diethylaminobutyl)-1,5-naphthyridin-4-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
0.58 g	In n-heptane at 160℃; for 20h;

Reference： [1]Barlin; Tan [Australian Journal of Chemistry, 1985, vol. 38, # 6, p. 905 - 911]

26
[ 27431-62-5 ]
[ 80092-93-9 ]
[ 80092-67-7 ]

Yield	Reaction Conditions	Operation in experiment
29%	In ethanol for 1.5h; Heating;

Reference： [1]Kesten, Stephen J.; Degnan, Margaret J.; Hung, Jocelyn; McNamara, Dennis J.; Ortwine, Daniel F.; et al. [Journal of Medicinal Chemistry, 1992, vol. 35, # 19, p. 3429 - 3447]

27
[ 27431-62-5 ]
[ 91700-87-7 ]
[ 80092-77-9 ]

Yield	Reaction Conditions	Operation in experiment
80%	In ethanol for 1.5h; Heating;

Reference： [1]Kesten, Stephen J.; Degnan, Margaret J.; Hung, Jocelyn; McNamara, Dennis J.; Ortwine, Daniel F.; et al. [Journal of Medicinal Chemistry, 1992, vol. 35, # 19, p. 3429 - 3447]

28
[ 27431-62-5 ]
[ 26752-70-5 ]
[ 179343-21-6 ]

Yield	Reaction Conditions	Operation in experiment
64%	With aminosulfonic acid at 150℃; for 28h;

Reference： [1]Hamby, James M.; Connolly, Cleo J. C.; Schroeder, Mel C.; Winters, R. Thomas; Showalter, H. D. Hollis; Panek, Robert L.; Major, Terry C.; Olsewski, Bronislawa; Ryan, Michael J.; Dahring, Tawny; Lu, Gina H.; Keiser, Joan; Amar, Aneesa; Shen, Cindy; Kraker, Alan J.; Slintak, Veronika; Nelson, James M.; Fry, David W.; Bradford, Laura; Hallak, Hussein; Doherty, Annette M. [Journal of Medicinal Chemistry, 1997, vol. 40, # 15, p. 2296 - 2303]

29
[ 663176-28-1 ]
[ 27431-62-5 ]

Yield	Reaction Conditions	Operation in experiment
76%	With lithium aluminium tetrahydride In diethyl ether at 0 - 20℃; for 1h;

Reference： [1]Seguin, Helene; Gardette, Daniel; Moreau, Marie-France; Madelmont, Jean-Claude; Gramain, Jean-Claude [Synthetic Communications, 1998, vol. 28, # 22, p. 4257 - 4272]

30
[ 27431-62-5 ]
[ 220822-18-4 ]
3-(2,6-dichloro-phenyl)-7-(4-diethylamino-butylamino)-1H-[1,6]naphthyridin-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	In various solvent(s) for 16h; Heating;

Reference： [1]Thompson; Rewcastle; Boushelle; Hartl; Kraker; Lu; Batley; Panek; Hollis Showalter; Denny [Journal of Medicinal Chemistry, 2000, vol. 43, # 16, p. 3134 - 3147]

31
[ 27431-62-5 ]
[ 220822-21-9 ]
3-(2,6-dichlorophenyl)-7-[4-(diethylamino)butylamino]-1-methyl-1H-[1,6]naphthyridin-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%	In various solvent(s) for 24h; Heating;

Reference： [1]Thompson; Rewcastle; Boushelle; Hartl; Kraker; Lu; Batley; Panek; Hollis Showalter; Denny [Journal of Medicinal Chemistry, 2000, vol. 43, # 16, p. 3134 - 3147]

32
[ 27431-62-5 ]
[ 35382-88-8 ]
[ 853942-77-5 ]

Yield	Reaction Conditions	Operation in experiment
80%	In dimethyl sulfoxide at 20℃;
	In dimethyl sulfoxide

Reference： [1]Hasegawa, Hirohiko; Muraoka, Masami; Ohmori, Mikiko; Matsui, Kazuki; Kojima, Atsuyuki [Bioorganic and Medicinal Chemistry, 2005, vol. 13, # 11, p. 3721 - 3735]
[2]Hasegawa, Hirohiko; Muraoka, Masami; Matsui, Kazuki; Kojima, Atsuyuki [Bioorganic and Medicinal Chemistry Letters, 2003, vol. 13, # 20, p. 3471 - 3475]

33
[ 27431-62-5 ]
[ 239095-84-2 ]
[ 239095-87-5 ]

Yield	Reaction Conditions	Operation in experiment
100%	In tetrahydrofuran at 20℃; for 0.5h;

Reference： [1]Li, Jie Jack; Carson, Kenneth G.; Trivedi, Bharat K.; Yue, Wen Song; Ye, Qing; Glynn, Roberta A.; Miller, Steven R.; Connor, David T.; Roth, Bruce D.; Luly, Jay R.; Low, Joseph E.; Heilig, David J.; Yang, Weixing; Qin, Shixin; Hunt, Stephen [Bioorganic and Medicinal Chemistry, 2003, vol. 11, # 17, p. 3777 - 3790]

34
[ 27431-62-5 ]
[ 239095-84-2 ]
6,7-dichloro-N,N'-bis-(4-diethylamino-butyl)-quinoxaline-2,3-diamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
99%	In tetrahydrofuran Heating;

Reference： [1]Li, Jie Jack; Carson, Kenneth G.; Trivedi, Bharat K.; Yue, Wen Song; Ye, Qing; Glynn, Roberta A.; Miller, Steven R.; Connor, David T.; Roth, Bruce D.; Luly, Jay R.; Low, Joseph E.; Heilig, David J.; Yang, Weixing; Qin, Shixin; Hunt, Stephen [Bioorganic and Medicinal Chemistry, 2003, vol. 11, # 17, p. 3777 - 3790]

35
[ 852460-55-0 ]
[ 27431-62-5 ]
N'-[4-(2,4-dichloro-benzyloxy)-pyrimidin-2-yl]-N,N-diethyl-butane-1,4-diamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine In 1-methyl-pyrrolidin-2-one at 95℃;

Reference： [1]Purandare, Ashok V.; Gao, Aiming; Wan, Honghe; Somerville, John; Burke, Christine; Seachord, Carrie; Vaccaro, Wayne; Wityak, John; Poss, Michael A. [Bioorganic and Medicinal Chemistry Letters, 2005, vol. 15, # 10, p. 2669 - 2672]

36
[ 862370-78-3 ]
[ 27431-62-5 ]
[ 862370-79-4 ]

Yield	Reaction Conditions	Operation in experiment
72%	In 1,4-dioxane at 50℃;

Reference： [1]Thompson, Andrew M.; Delaney, Amy M.; Hamby, James M.; Schroeder, Mel C.; Spoon, Teresa A.; Crean, Sheila M.; Showalter, H. D. Hollis; Denny, William A. [Journal of Medicinal Chemistry, 2005, vol. 48, # 14, p. 4628 - 4653]

37
[ 862370-64-7 ]
[ 27431-62-5 ]
N-[3-(2,6-dichlorophenyl)-7-fluoro-1,6-naphthyridin-2-yl]-N'-[4-(diethylamino)butyl]urea [ No CAS ]
N-[3-(2,6-dichlorophenyl)-7-[[4-(diethylamino)butyl]amino]-1,6-naphthyridin-2-yl]-N'-[4-(diethylamino)butyl]urea [ No CAS ]
[ 293301-19-6 ]

Yield	Reaction Conditions	Operation in experiment
1: 75% 2: 9% 3: 9%	In various solvent(s) at 120℃; for 2h;

Reference： [1]Thompson, Andrew M.; Delaney, Amy M.; Hamby, James M.; Schroeder, Mel C.; Spoon, Teresa A.; Crean, Sheila M.; Showalter, H. D. Hollis; Denny, William A. [Journal of Medicinal Chemistry, 2005, vol. 48, # 14, p. 4628 - 4653]

38
[ 27431-62-5 ]
[ 293301-19-6 ]
[ 862370-06-7 ]

Yield	Reaction Conditions	Operation in experiment
36%	In 2-ethoxy-ethanol for 120h; Heating;

Reference： [1]Thompson, Andrew M.; Delaney, Amy M.; Hamby, James M.; Schroeder, Mel C.; Spoon, Teresa A.; Crean, Sheila M.; Showalter, H. D. Hollis; Denny, William A. [Journal of Medicinal Chemistry, 2005, vol. 48, # 14, p. 4628 - 4653]

39
[ 681247-06-3 ]
[ 27431-62-5 ]
2-[2-(4-diethylamino-butylcarbamoyl)-benzenesulfonylamino]-5,6,7,8-tetrahydro-naphthalene-1-carboxylic acid methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 2-([1-(methoxycarbonyl)-5,6,7,8-tetrahydro-2-naphthalenyl]amino}sulfonyl)benzoic acid With 4-methyl-morpholine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: 4-(diethylamino)butylamine In N,N-dimethyl-formamide at 20℃;

Reference： [1]Sheppard, George S.; Wang, Jieyi; Kawai, Megumi; Fidanze, Steve D.; BaMaung, Nwe Y.; Erickson, Scott A.; Barnes, David M.; Tedrow, Jason S.; Kolaczkowski, Lawrence; Vasudevan, Anil; Park, David C.; Wang, Gary T.; Sanders, William J.; Mantei, Robert A.; Palazzo, Fabio; Tucker-Garcia, Lora; Lou, Pingping; Zhang, Qian; Park, Chang H.; Kim, Ki H.; Petros, Andrew; Olejniczak, Edward; Nettesheim, David; Hajduk, Phillip; Henkin, Jack; Lesniewski, Richard; Davidsen, Steven K.; Bell, Randy L. [Journal of Medicinal Chemistry, 2006, vol. 49, # 13, p. 3832 - 3849]

40
[ 907190-39-0 ]
[ 27431-62-5 ]
4-[5-(3,5-dichloro-phenyl)-2-naphthalen-2-yl-2H-pyrazol-3-yl]-N-(4-diethylamino-butyl)-butyramide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃;

Reference： [1]Pinkerton, Anthony B.; Huang, Dehua; Cube, Rowena V.; Hutchinson, John H.; Struthers, Mary; Ayala, Julia M.; Vicario, Pasquale P.; Patel, Sima R.; Wisniewski, Thomas; DeMartino, Julie A.; Vernier, Jean-Michel [Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 3, p. 807 - 813]

41
[ 27431-62-5 ]
3-(4-diethylamino-butyl)-4-phenyl-3,4-dihydro-1H-quinazolin-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 80 percent / dimethylsulfoxide / 20 °C 2: 98 percent / NaBH₄ / dimethylformamide / cooling
	Multi-step reaction with 2 steps 1: dimethylsulfoxide 2: NaBH₄ / dimethylformamide

Reference： [1]Hasegawa, Hirohiko; Muraoka, Masami; Ohmori, Mikiko; Matsui, Kazuki; Kojima, Atsuyuki [Bioorganic and Medicinal Chemistry, 2005, vol. 13, # 11, p. 3721 - 3735]
[2]Hasegawa, Hirohiko; Muraoka, Masami; Matsui, Kazuki; Kojima, Atsuyuki [Bioorganic and Medicinal Chemistry Letters, 2003, vol. 13, # 20, p. 3471 - 3475]

42
[ 27431-62-5 ]
1-[3-(2,6-dichloro-phenyl)-7-(4-diethylamino-butylamino)-[1,6]naphthyridin-2-yl]-3-ethyl-urea [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: 36 percent / 2-ethoxy-ethanol / 120 h / Heating 2.1: NaH / dimethylsulfoxide / 0.67 h 2.2: 63 percent / dimethylsulfoxide / 16 h / 20 °C

Reference： [1]Thompson, Andrew M.; Delaney, Amy M.; Hamby, James M.; Schroeder, Mel C.; Spoon, Teresa A.; Crean, Sheila M.; Showalter, H. D. Hollis; Denny, William A. [Journal of Medicinal Chemistry, 2005, vol. 48, # 14, p. 4628 - 4653]

43
[ 27431-62-5 ]
1-tert-butyl-3-[3-(2,6-dichloro-phenyl)-7-(4-diethylamino-butylamino)-[1,6]naphthyridin-2-yl]-urea [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: 36 percent / 2-ethoxy-ethanol / 120 h / Heating 2.1: NaH / dimethylsulfoxide / 0.67 h 2.2: 59 percent / dimethylsulfoxide / 17 h / 20 °C

Reference： [1]Thompson, Andrew M.; Delaney, Amy M.; Hamby, James M.; Schroeder, Mel C.; Spoon, Teresa A.; Crean, Sheila M.; Showalter, H. D. Hollis; Denny, William A. [Journal of Medicinal Chemistry, 2005, vol. 48, # 14, p. 4628 - 4653]

44
[ 27431-62-5 ]
[ 88593-05-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 170 °C 2: lithium alanate; diethyl ether

Reference： [1]Rice et al. [Journal of the American Chemical Society, 1953, vol. 75, p. 4911,4914]

45
[ 27431-62-5 ]
[ 651734-86-0 ]
[ 651734-47-3 ]

Yield	Reaction Conditions	Operation in experiment
86%	In 1,4-dioxane at 75℃; for 24h;	32 EXAMPLE 3; 21-Cyclopentyl-7-(4-diethylamino-butylamino)-3-(3-ethoxy-2,6-difluoro-phenyl)-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one Using Procedure K, described above, 0.74 g (1.69 mmol) of 3-(3-ethoxy-2,6-difluoro-phenyl)-1-(1-ethyl-propyl)-7-methanesulfinyl-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one and 4-(diethylamino)butylamine in 20 ML of dioxane were reacted.Chromatography with 9:1:0.5 ethyl acetate/ethanol/ triethylamine gave 0.75 g (86%) of the title compound as a solid: mp 129° C.-130° C. 130° C. MS (APCI) (m+1)/z 5127.47.Analysis calculated for C27H38N6F2O2: C, 62.77; H, 7.41; N, 16.27.Found: C, 62.79; H, 7.35; N, 16.10.

Reference： [1]Current Patent Assignee: PFIZER INC - US2004/19210, 2004, A1 Location in patent: Page 24; 18

46
[ 27431-62-5 ]
[ 651734-99-5 ]
1-Cyclopentyl-7-(4-diethylamino-butylamino)-3-(2,6-difluoro-3,5-dimethoxy-phenyl)-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	In 1,4-dioxane for 10h; Heating / reflux;	2 In a 1-L round bottom flask, 8.00 g (17.78 mmol) of 1-cyclopentyl-3-(2,6-difluoro- 3,5-dimethoxy-phenyl)-7-methylsulfinyl-3,4-dihydro-1H-pyrimido[4,5-£/]pyrimidin-2-one in 260 mL of dioxane was treated with 5.1O g (35.36 mmol) of 4-diethylamino-butylamine and heated at reflux for 10 hours under nitrogen atmosphere. The dioxane was evaporated in vacuo. The crude product was purified using medium-pressure chromatography eluting with a gradient of 9:0.5:0.25 to 9:1:0.5 ethyl acetate/methanol/triethylamine to give 8.14 g (86%) of the title compound as a pure partially crystalline solid. A 50 mg portion of the solid was recrystallized with 25% ethanol in hexanes to give 35 mg of title compound as pure crystalline solid: mp 132°C-133°C. MS (APCI) (m+1 )/z 533.3.
86%	In 1,4-dioxane for 10h; Heating / reflux;	2 EXAMPLE 2; 1-Cyclopentyl-7-(4-diethylamino-butylamino)-3-(2,6-difluoro-3,5-dimethoxy-phenyl)-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one EXAMPLE 2 1-Cyclopentyl-7-(4-diethylamino-butylamino)-3-(2,6-difluoro-3,5-dimethoxy-phenyl)-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one In a 1-L round bottom flask, 8.00 g (17.78 mmol) of 1-cyclopentyl-3-(2,6-difluoro-3,5-dimethoxy-phenyl)-7-methylsulfinyl-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one in 260 ML of dioxane was treated with 5.10 g (35.36 mmol) of 4-diethylamino-butylamine and heated at reflux for 10 hours under nitrogen atmosphere.The dioxane was evaporated in vacuo.The crude product was purified using medium-pressure chromatography eluding with a gradient of 9:0.5:0.25 to 9:1:0.5 ethyl acetate/methanol/triethylamine to give 8.14 g (86%) of the title compound as a pure partially crystalline solid.A 50 mg portion of the solid was recrystallized with 25% ethanol in hexanes to give 35 mg of title compound as pure crystalline solid: mp 132° C.-133° C. MS (APCI) (m+1)/z 533.3.

Reference： [1]Current Patent Assignee: PFIZER INC - WO2006/38112, 2006, A1 Location in patent: Page/Page column 44
[2]Current Patent Assignee: PFIZER INC - US2004/19210, 2004, A1 Location in patent: Page 19

47
[ 27431-62-5 ]
[ 651734-99-5 ]
[ 651734-22-4 ]

Yield	Reaction Conditions	Operation in experiment
83%	In 1,4-dioxane at 75℃; for 24h;	9 EXAMPLE 9; 1-Cyclopropyl-7-(4-diethylamino-butylamino)-3-(2,6-difluoro-3,5-dimethoxy-phenyl)-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one Using Procedure K, 0.63 g (1.48 mmol) of 1-cyclopropyl-3-(2,6-difluoro-3,5-dimethoxy-phenyl)-7-methanesulfinyl-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one and 4-(diethylamino)butylamine in 20 ML of dioxane were reacted.Chromatography with 9:1:0.5 ethyl acetate/ethanol/triethylamine gave 0.62 g (83%) of the title compound as a solid: mp 139° C.-141° C. MS (APCI) (m+1)/z 505.2.Analysis calculated for C25H34N6F2O3: C, 59.51; H, 6.79; N, 16.66. Found: C, 59.56; H, 6.77; N, 16.49.

Reference： [1]Current Patent Assignee: PFIZER INC - US2004/19210, 2004, A1 Location in patent: Page 20

48
[ 27431-62-5 ]
aqueous Na₂ CO₃ [ No CAS ]
[ 121-44-8 ]
3-(2,6-dichlorophenyl)-7-[4-(diethylamino)butylamino]-1-methyl-1H-[1,6]naphthyridin-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In (+/-)-2-pentanol	F Preparation of 3-(2,6-dichlorophenyl)-7-[4-(diethylamino)butylamino]-1-methyl-1H-[1,6]naphthyridin-2-one Example F Preparation of 3-(2,6-dichlorophenyl)-7-[4-(diethylamino)butylamino]-1-methyl-1H-[1,6]naphthyridin-2-one A solution of (IX, where R2 is methyl) (104 mg, 0.32 mmol) and 4-(diethylamino)butylamine (0.51 g, 3.54 mmnol) in 2-pentanol (10 mL) was stirred at reflux for 1 day. The solvent was removed under reduced pressure, then the residue was diluted with aqueous Na2 CO3 (50 mL) and extracted with EtOAc (350 mL). The solvent was removed, then chromatography of the residue on silica gel, eluding with 2-5% MeOH/CH2 Cl2 containing 0.3% Et3 N, gave a crude product, which was treated with aqueous Na2 CO3 and extracted with CH2 Cl2 (450 mL). The solvent was removed, then chromatography of the residue on alumina, eluding with 0.5-1% MeOH/CH2 Cl2, gave 3-(2,6-dichlorophenyl)-7-[4-(diethylamino)butylamino]-1-methyl-1H-[1,6]naphthyridin-2-one; (125 mg, 87%): mp (pentane) 123-124.5° C. 1 H NMR (CDCl3) δ 8.32 (s, 1H, H-5), 7.52 (s, 1H, H-4), 7.39 (d, J=8.4 Hz, 2H, H-3',5'), 7.24 (dd, J=8.5, 7.6 Hz, 1H, H-4'), 6.03 (s, 1H, H-8), 5.59 (br s, 1H, NH), 3.64 (s, 3H, NCH3), 3.35 (td, J=6.5, 4.6 Hz, 2H, NHCH2), 2.56 (q, J=7.2 Hz, 4H, N(CH2)2), 2.49 (t, J=7.1 Hz, 2H, NCH2), 1.74 (pentet, J=7.0 Hz, 2H, CH2), 1.62 (pentet, J=7.0 Hz, 2H, CH2), 1.05 (t, J=7.1 Hz, 6H, 2CH3). 13 C NMR δ 160.81, 159.92 (2 s, C-2,7), 150.80 (d, C-5), 147.17 (s, C-8a), 138.32 (d, C-4), 135.86 (s, 2 C, C-2',6'), 134.92 (s, C-1'), 129.51 (d, C-4'), 127.91 (d, 2 C, C-3',5'), 123.89 (s, C-3), 109.21 (s, C-4a), 86.72 (d, C-8), 52.57 (t, NCH2), 46.69 (t, 2 C, N(CH2)2), 42.47 (t, NCH2), 29.34 (q, NCH3), 27.37, 24.91 (2 t, 2CH2), 11.47 (q, 2 C, 2CH3). Analysis calculated for C23 H28 Cl2 N4 O requires: C, 61.8; H, 6.3; N, 12.5%. Found: C, 61.6; H, 6.5; N, 12.4%.

Reference： [1]Current Patent Assignee: PFIZER INC - US6150359, 2000, A

49
[ 27431-62-5 ]
[ 651734-83-7 ]
[ 651734-22-4 ]

Yield	Reaction Conditions	Operation in experiment
83%	In 1,4-dioxane at 75℃; for 24h;	K; 9 Using Procedure K, 0.63 g (1.48 mmol) of 1-cyclopropyl-3-(2,6-difluoro-3,5- dimethoxy-phenyl)-7-methanesulfinyl-3,4-dihydro-1 H-pyrimido[4,5-d]pyrimidin-2-one and4-(diethylamino)butylamine in 20 mL of dioxane were reacted. Chromatography with9:1 :0.5 ethyl acetate/ethanol/triethylamine gave 0.62 g (83%) of the title compound as a solid: mp 139°C-141°C.MS (APCI) (m+1 )/z 505.2. Analysis calculated for C25H34N6F2O3: C, 59.51 ; H, 6.79; N, 16.66. Found: C, 59.56; H, 6.77; N, 16.49.Procedure K General Procedure for the Reaction of Substituted Alkylamines with SulfoxidesTo a sulfoxide prepared above was added a solution of 3 equivalents of amine in dry dioxane. The reaction was warmed to 75°C for 24 hours, then concentrated in vacuo. The residue was dissolved in dichloromethane. The dichloromethane solution was extracted twice with a saturated solution of sodium bicarbonate then once with a saturated solution of sodium chloride, dried with magnesium sulfate, and concentrated in vacuo. The crude product was chromatographed using a Biotage Quad 3 chromatographic apparatus with a 90 g silica gel column and the appropriate solvent systems. Pure fractions were combined and concentrated in vacuo. The residue was stirred with ether and concentrated in vacuo to give the desired product.

Reference： [1]Current Patent Assignee: PFIZER INC - WO2006/38112, 2006, A1 Location in patent: Page/Page column 40; 47

50
[ 27431-62-5 ]
[ 192705-78-5 ]
[ 862370-79-4 ]

Yield	Reaction Conditions	Operation in experiment
	With aminosulfonic acid at 140 - 180℃;	4 The starting material (synthesis described in: J. Med. Chem., 1997, 40, 2296-2303), sulfamic acid (2 equivalents) and 4-(diethylamino)butylamine (~15 equivalents) are heated at 150 0C according to the procedure described in J. Med. Chem., 1997, 40, 2296-2303. At the end of the reaction excess amine is removed in vacuo. The residue is suspended in a mixture of water and saturated aqueous sodium bicarbonate solution. This mixture is extracted with dichloromethane. The combined organic extracts are washed with saturated aqueous sodium bicarbonate solution, brine, and dried over sodium sulfate. Filtration and evaporation of the solvent yields a crude product. Further purification was achieved by flash chromatography on silica gel.The required isocyanate for step 2 is prepared from 2-amino ethyl phosphonic acid diethyl ester and phosgene according to a procedure from Organikum, 17th edition, VEB Deutscher Verlag der Wissenschaften, Berlin 1988, page 428. A solution of 2-amino ethyl phosphonic acid diethyl ester in an organic solvent such as dichloromethane or toluene is added to a cooled solution of phosgene in an organic solvent such as toluene or dichloromethane. After the addition of the amine, the cooling is removed and the solution was heated at 100 0C with further phosgene addition. Upon cessation of hydrochloric acid evolution, excess phosgene is removed and the solvents were removed in vacuo. The product of step 1 is treated with sodium hydride (~1.1 equivalents) in an organic solvent such as dimethylformamide, according to the procedure described in J Med. Chem., 1997, 40, 2296-2303. The phosphonate-containing EPO isocyanate is added and the reaction mixture is stirred at room temperature. At the end of the reaction, the mixture is filtered and the solvent is removed in vacuo. The crude material is partitioned between water and ethyl acetate. The aqueous layer is extracted with ethyl acetate and the combined organic layers washed with brine and dried over sodium sulfate. Filtration and evaporation of solvents yields the crude product. Further purification is achieved by flash chromatography on silica gel.

Reference： [1]Current Patent Assignee: GILEAD SCIENCES INC - WO2006/47507, 2006, A2 Location in patent: Page/Page column 147-148

51
[ 27431-62-5 ]
[ 530-62-1 ]
[ 85052-84-2 ]
N'-[4-(diethylamino)butyl]-N-(1-methylethyl)-N-[2-(phenylsulfonyl)ethyl]urea [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
2.29 g (26.2%)	In tetrahydrofuran; dichloromethane	88 N'-[4-(Diethylamino)butyl]-N-(1-methylethyl)-N-[2-(phenylsulfonyl)ethyl]urea EXAMPLE 88 N'-[4-(Diethylamino)butyl]-N-(1-methylethyl)-N-[2-(phenylsulfonyl)ethyl]urea A solution of 4.40 g (0.0272 mole) of 1,1'-carbonyldiimidazole and 3.46 g (0.024 mole) of N,N-diethyl-1,4-butanediamine in 400 ml of tetrahydrofuran was stirred at room temperature for 1 hr. A solution of 5.00 g (0.0220 mole) of N-[2-(phenylsulfonyl)ethyl]-2-propanamine in 50 ml of tetrahydrofuran was added, and the solution was refluxed overnight. The solvent was removed in vacuo, and the residue was dissolved in 600 ml of a 50/50 mixture of ether and methylene chloride. The organic solution was extracted with three portions of water and was dried over magnesium sulfate. The solvent was removed in vacuo to give an oil. Flash chromatography on silica gel (methanol) gave 2.29 g (26.2%) of clear colorless oil: 1 H NMR (CDCl3)δ7.4-8.05 (m, 5, aromatic); 4.95 (br t, 1, NH), 4.03 (m, 1, J=3 HZ, (CH3)2 CH) 3.40 (S, 4, SO2 CH2 CH2 --) 3.0-3.3 (br m, 2, NHCH2), 2.2-2.8 (m, 6, --CH2 N(CH2 CH3)2, 1.3-1.6 (m, 4, CH2 CH2 CH2 N), 1.10 (d, 6, J=3 HZ, (CH3)2 CH), 1.0 (t, 6, N(CH2 CH3)2. Analysis: Calculated for C20 H35 N3 O3 S: C, 60.42; H, 8.87; N, 10.57. Found: C, 60.05, H, 8.94; N, 10.45.

Reference： [1]Current Patent Assignee: PFIZER INC - US4597902, 1986, A

52
[ 27431-62-5 ]
[ 6626-40-0 ]
[ 108-95-2 ]
7-chloro-10-[(4-diethylaminobutyl)amino]-2-methoxypyrido[3,2-b]quinoline dihydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride In ethanol; acetone	2 7-Chloro-10-[(4-diethylaminobutyl)amino]-2-methoxypyrido[3,2-b]quinoline dihydrochloride EXAMPLE 2 7-Chloro-10-[(4-diethylaminobutyl)amino]-2-methoxypyrido[3,2-b]quinoline dihydrochloride A mixture of 2.8 g. of 7,10-dichloro-2-methoxypyrido[3,2-b]quinoline, 1.5 g. of 4-diethylaminobutylamine and 6.5 g. of phenol is heated at 100° C. for 3 hours. The reaction is cooled, 20 ml. of ethanol is added and this mixture is poured into a mixture of 200 ml. of acetone and 2.5 ml. of concentrated hydrochloric acid. The yellow solic is collected, air-dried and recrystallized from ethanol, giving the desired product, mp. 246°-274° C. (dec.).

Reference： [1]Current Patent Assignee: PFIZER INC - US4226869, 1980, A

53
[ 27431-62-5 ]
[4-carbamoyl-3-(2,3,6-trifluoro-4-methyl-benzyloxy)-isothiazol-5-yl]-carbamic acid phenyl ester [ No CAS ]
5-[3-(4-Diethylamino-butyl)-ureido]-3-(2,3,6-trifluoro-4-methyl-benzyloxy)-isothiazole-4-carboxylic acid amide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		54 5-[3-(4-Diethylamino-butyl)-ureido]-3-(2,3,6-trifluoro-4-methyl-benzyloxy)-isothiazole-4-carboxylic acid amide EXAMPLE 54 5-[3-(4-Diethylamino-butyl)-ureido]-3-(2,3,6-trifluoro-4-methyl-benzyloxy)-isothiazole-4-carboxylic acid amide The title compound was prepared from [4-carbamoyl-3-(2,3,6-trifluoro-4-methyl-benzyloxy)-isothiazol-5-yl]-carbamic acid phenyl ester and N,N-diethyl-butane-1,4-diamine by the procedure analogous to Example 1. MS (APCI, ml) 488 [M+H]+.

Reference： [1]Current Patent Assignee: PFIZER INC - US6235764, 2001, B1

54
[ 27431-62-5 ]
[ 251371-82-1 ]
[ 251370-23-7 ]

Yield	Reaction Conditions	Operation in experiment
0.34 g (56%)	With trifluoroacetic acid In hydrogenchloride; methanol; ethyl acetate; acetonitrile	53 7-(4-Diethylamino-butylamino)-3-(3,5-dimethoxy-phenyl)-1-ethyl-3,4-dihydro-pyrimido[4,5-d]pyrimidin-2(1H)-one EXAMPLE 53 7-(4-Diethylamino-butylamino)-3-(3,5-dimethoxy-phenyl)-1-ethyl-3,4-dihydro-pyrimido[4,5-d]pyrimidin-2(1H)-one A mixture of 3-(3,5-dimethoxy-phenyl)-1-ethyl-7-methanesulfinyl-3,4-dihydro-pyrimido[4,5-d]pyrimidin-2(1H)-one (0.5 g, 1.33 mmol), 4-diethylaminobutylamine (0.38 g, 2.66 mmol,) and trifluoroacetic acid (0.31 g, 2.66 mmol) in acetonitrile (6 mL) was heated in a sealed tube at 90° C. for 18 hours. The solvent was removed under reduced pressure and the residue taken up in 1N HCl. The solution was made basic with 50% NaOH and extracted twice with dichloromethane. The combined organic layers were dried over magnesium sulfate, filtered, and evaporated. The residue was purified by radial chromatography eluding with a solvent mixture of ethyl acetate/methanol/ethyl (89:10:1 v/v/v) to give 0.34 g (56%) of the titled compound: mp 83-85° C. Mass Spectrum (APCI, 80/20 CH3CN/H2O, Probe=450° C.) (m+1)/z 458.2 Analysis calculated for C24H36N6O3: C, 63.13; H, 7.95; N, 8.41. Found: C, 62.85; H,7.84; N, 18.06.

Reference： [1]Current Patent Assignee: PFIZER INC; PPG INDUSTRIES INC - US2004/44012, 2004, A1

55
[ 27431-62-5 ]
[ 401816-84-0 ]
[ 401816-95-3 ]

Yield	Reaction Conditions	Operation in experiment
		92 N-[4-(diethylamino)butyl]-N-(4-{6-(trifluoromethyl)-2-[4-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyridin-3-yl}pyrimidin-2-yl)amine Example 92 N-[4-(diethylamino)butyl]-N-(4-{6-(trifluoromethyl)-2-[4-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyridin-3-yl}pyrimidin-2-yl)amine In an analogous procedure to Example 88(d), methyl 4-{6-(trifluoromethyl)-2-[4-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyridin-3-yl}pyrimidin-2-yl sulfone (0.02 g) and 4-(diethylamino)butylamine (0.04 mL) gave the title compound; 1H NMR (d6-DMSO) δ 9.48 (1H, s), 8.44 (1H, bs), 8.14 (1H, d), 7.83 (4H, dd), 7.65 (1H, d), 6.96 (1H, bs), 6.36 (1H, bs), 2.36 (2H, bs), 2.28 (4H, bs), 1.44 (4H, bt), 1.33 (2H, bd); m/z 450, 535.

Reference： [1]Current Patent Assignee: GLAXOSMITHKLINE PLC - US2004/53942, 2004, A1

56
[ 27431-62-5 ]
[ 401816-92-0 ]
[ 401816-97-5 ]

Yield	Reaction Conditions	Operation in experiment
		94 N-{4-[2-(3-chlorophenyl)-6-(trifluoromethyl)pyrazolo[1,5-a]pyridin-3-yl]pyrimidin-2-yl}-N-[4-(diethylamino)butyl]amine Example 94 N-{4-[2-(3-chlorophenyl)-6-(trifluoromethyl)pyrazolo[1,5-a]pyridin-3-yl]pyrimidin-2-yl}-N-[4-(diethylamino)butyl]amine In an analogous procedure to Example 88(d), 4-[2-(3-chlorophenyl)-6-(trifluoromethyl)pyrazolo[1,5-a]pyridin-3-yl]pyrimidin-2-yl methyl sulfone (0.02 g) and 4-(diethylamino)butylamine (0.04 mL) gave the title compound; 1H NMR (d6DMSO) δ 9.51 (1H, s), 8.47 (1H, bs), 8.14 (1H, d), 7.73-7.66 (2H, m), 7.6-17.51 (3H, m), 7.31 (1H, bs), 6.32 (1H, bs), 3.27 (2H, bs), 2.41 (4H, q), 2.35 (2H, t), 1.53 (2H, m), 1.43 (2H, m), 0.91 (6H, t); m/z 517(M+1)+.

Reference： [1]Current Patent Assignee: GLAXOSMITHKLINE PLC - US2004/53942, 2004, A1

57
[ 27431-62-5 ]
[ 5779-95-3 ]
[ 1046808-14-3 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 4-(diethylamino)butylamine; 3,5-dimethylbenzaldehyde In methanol at 20℃; Stage #2: With sodium tetrahydroborate In methanol for 1h;	7 Diethyl(3,5-dimethylbenzyl)[N-(3,5-dimethylbenzyl)-2-naphthalenecarboxamidobutyl]ammonium bromide (Compound 133) EXAMPLE 7 Diethyl(3,5-dimethylbenzyl)[N-(3,5-dimethylbenzyl)-2-naphthalenecarboxamidobutyl]ammonium bromide (Compound 133) A solution of 209 mg (1.56 mmol) of 3,5-dimethylbenzaldehyde and 204 mg (1.42 mmol) of 4-(diethylamino)butylamine in 25 mL of methanol was stirred at room temperature overnight. To this solution was added 94 mg (2.49 mmol) of sodium borohydride. After 1 hr of stirring, the mixture was poured into water and acidified with 5% aqueous hydrochloric acid. The aqueous solution was extracted with diethyl ether three times, and the ether extracts were discarded. The aqueous fraction was basified with saturated sodium bicarbonate, and then extracted thoroughly with diethyl ether to give 185 mg (0.71 mmol) of N-[4-(diethylamino)butyl]-N-(3,5-dimethylbenzyl)amine.

Reference： [1]Current Patent Assignee: CROPSOLUTION - US2008/200461, 2008, A1 Location in patent: Page/Page column 93

58
[ 27431-62-5 ]
[ 66-99-9 ]
[ 1046808-16-5 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 4-(diethylamino)butylamine; β-naphthaldehyde In methanol at 20℃; Stage #2: With sodium tetrahydroborate In methanol at 0℃; for 1h;	10 N-(4-Diethylaminobutyl)-N-(2-naphthylmethyl)-2-naphthalenesulfonamide (Compound 199) A solution of 370 mg (2.37 mmol) of 2-naphthaldehyde and 326 mg (2.26 mmol) of 4-(diethylamino)butylamine in 5 mL of methanol was stirred at room temperature overnight. The solution was cooled to 0° C., and 233 mg (6.16 mmol) of sodium borohydride was added. After 1 hr of stirring, aqueous sodium hydroxide (1 mL) was added to the mixture. The product was extracted with diethyl ether several times, and the combined ether extracts were dried with sodium sulfate. The ether was removed by rotoevaporation to give 545 mg (1.92 mmol) of N-[4-(diethylamino)butyl]-N-(2-naphthylmethyl)amine.

Reference： [1]Current Patent Assignee: CROPSOLUTION - US2008/200461, 2008, A1 Location in patent: Page/Page column 93

59
[ 27431-62-5 ]
[ 64-18-6 ]
[ 27129-86-8 ]
diethyl(3,5-dimethylbenzyl)[bis-(3,5-dimethylbenzyl)aminobutyl]ammonium formate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 4-(diethylamino)butylamine; 1-bromomethyl-3,5-dimethylbenzene With sodium hydrogencarbonate In tetrahydrofuran; water at 20℃; for 22h; Stage #2: formic acid In water; acetonitrile HPLC;	1 Diethyl(3,5-dimethylbenzyl)[bis-(3,5-dimethylbenzyl)aminobutyl]ammonium formate (Compound 28) EXAMPLE 1 Diethyl(3,5-dimethylbenzyl)[bis-(3,5-dimethylbenzyl)aminobutyl]ammonium formate (Compound 28) A mixture of 29 mg (0.2 mmol) of diethylaminobutylamine, 119 mg (0.6 mmol) of 3,5-dimethylbenzyl bromide, and 0.6 mL (0.6 mmol) of 1M NaHCO3, and 2 mL of THF in an 8 mL sealed vial was shaken at room temperature for 22 hr. The reaction product mixture was syringe filtered, and then purified by preparative HPLC using acetonitrile/0.05% aqueous formic acid. Lyophilization of the HPLC fractions gave 48 mg (0.09 mmol) of diethyl(3,5-dimethylbenzyl)[bis-(3,5-dimethylbenzyl)-aminobutyl]-ammonium formate as a gum. 1H NMR (CDCl3): δ1.39 (t, 6H), 1.55 (br m, 2), 1.75 (br m, 2), 2.29 (s,12), 2.31 (s,6), 3.45 (s,4), 4.50 (s,2), 6.88-6.95, (m, 9), and 8.68 ppm (s,1). MS m/z: 499.4 (M+).

Reference： [1]Current Patent Assignee: CROPSOLUTION - US2008/200461, 2008, A1 Location in patent: Page/Page column 91-92

60
[ 27431-62-5 ]
[ 97227-33-3 ]
[ 1192137-85-1 ]

Yield	Reaction Conditions	Operation in experiment
72%	at 80℃; for 12h; Inert atmosphere;
	at 80℃; Inert atmosphere;

Reference： [1]Wang, Qian; Liang, Wenting; Wei, Xueqin; Wu, Wanhua; Inoue, Yoshihisa; Yang, Cheng; Liu, Yu [Organic Letters, 2020, vol. 22, # 24, p. 9757 - 9761]
[2]Ke, Chenfeng; Liu, Yu; Yang, Cheng; Mori, Tadashi; Inoue, Yoshihisa; Wada, Takehiko [Angewandte Chemie - International Edition, 2009, vol. 48, # 36, p. 6675 - 6677][Angewandte Chemie, 2009, vol. 121, # 36, p. 6803 - 6805]

61
[ 97020-69-4 ]
[ 27431-62-5 ]

Yield	Reaction Conditions	Operation in experiment
61%	With hydrazine hydrate In ethanol; water for 12h; Reflux;	1.1.3. General procedure for preparation of compounds 18 to 22 General procedure: Compound 13-17 (1 eq.) was dissolved in EtOH (100 mL for 2.5 to 5 g of phthalimide) and hydrazine hydrate (aqueous solution, 60% wt, 4 eq.) was added dropwise under stirring. The mixture was refluxed for 12 h and then cooled down to rt. The obtained suspension was filtered and the precipitate was washed thoroughly with EtOH. The filtrate was cooled in an ice-water bath and treated dropwise with a concentrated aqueous HCl solution (6 eq.). The formed solid was removed by fitration and washed with EtOH (approximately 100 mL for 5 g of phthalimide). One supplementary fraction of solid was removed by reacidification of the filtrate (if precipitate didn’t appear, the mixture was allowed to cool at 4 °C for 1 h). The filtrate was concentrated under reduced pressure, cooled in an ice-water bath and then gently dissolved in a minimum amount of an aqueous KOH solution (50% wt). The obtained solution was extracted with Et2O (3 × 75 mL for 5 g of phthalimide). The combined organic layers were dried over MgSO4, filtered and concentrated under reduced pressure to afford a transparent to pale yellow oily liquid. This crude product was used directly for the next step or purified by distillation under reduced pressure to yield pure amines.
41%	With hydrazine hydrate In ethanol for 8h; Reflux;
33%	With hydrazine hydrate In ethanol for 3h; Reflux;

With hydrazine hydrate In methanol for 4h; Reflux;

Reference： [1]Ghedira, Donia; Voissière, Aurélien; Peyrode, Caroline; Kraiem, Jamil; Gerard, Yvain; Maubert, Elise; Vivier, Magali; Miot-Noirault, Elisabeth; Chezal, Jean-Michel; Farhat, Farhat; Weber, Valérie [European Journal of Medicinal Chemistry, 2018, vol. 158, p. 51 - 67]
[2]Ke, Chenfeng; Liu, Yu; Yang, Cheng; Mori, Tadashi; Inoue, Yoshihisa; Wada, Takehiko [Angewandte Chemie - International Edition, 2009, vol. 48, # 36, p. 6675 - 6677][Angewandte Chemie, 2009, vol. 121, # 36, p. 6803 - 6805]
[3]Robaa, Dina; Wagner, Tobias; Luise, Chiara; Carlino, Luca; McMillan, Joel; Flaig, Ralf; Schüle, Roland; Jung, Manfred; Sippl, Wolfgang [ChemMedChem, 2016, vol. 11, # 20, p. 2327 - 2338]
[4]Patel, Dushyant V.; Patel, Nirav R.; Kanhed, Ashish M.; Patel, Sagar P.; Sinha, Anshuman; Kansara, Deep D.; Mecwan, Annie R.; Patel, Sarvangee B.; Upadhyay, Pragnesh N.; Patel, Kishan B.; Shah, Dharti B.; Prajapati, Navnit K.; Murumkar, Prashant R.; Patel, Kirti V.; Yadav, Mange Ram [ACS Chemical Neuroscience, 2019, vol. 10, # 8, p. 3635 - 3661]

62
[ 1262500-36-6 ]
[ 27431-62-5 ]

Yield	Reaction Conditions	Operation in experiment
63%	With trifluoroacetic acid In dichloromethane at 20℃; for 1h;

Reference： [1]Location in patent: experimental part Lavrado, João; Cabal, Ghislain G.; Prudêncio, Miguel; Mota, Maria M.; Gut, Jiri; Rosenthal, Philip J.; Díaz, Cecília; Guedes, Rita C.; Dos Santos, Daniel J. V. A.; Bichenkovß, Elena; Douglaŝ, Kenneth T.; Moreira, Rui; Paulo, Alexandra [Journal of Medicinal Chemistry, 2011, vol. 54, # 3, p. 734 - 750]

63
[ 27431-62-5 ]
[ 1339940-10-1 ]
C₂₇H₃₁FN₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In methanol; dichloromethane at 20℃;	5.4. General procedures for the synthesis of β-carbolines 3a-d, 4a-d, 5a-d, 6a-d, 7a-d and 8a-d General procedure: A mixture of β-carboline-1-carboxaldehydes (1 mmol), diamine (1.2 mmol), anhydrous methanol (6 mL) and anhydrous CH2Cl2 (3 mL) was stirred at room temperature overnight. The solvent was evaporated under vacuum to give the crude schiff base, which was used directly in the next step without further purification.

Reference： [1]Location in patent: experimental part Chen, Zhiyong; Cao, Rihui; Shi, Buxi; Guo, Liang; Sun, Jie; Ma, Qin; Fan, Wenxi; Song, Huacan [European Journal of Medicinal Chemistry, 2011, vol. 46, # 10, p. 5127 - 5137]

64
[ 27431-62-5 ]
[ 1339940-11-2 ]
C₂₇H₃₁ClN₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In methanol; dichloromethane at 20℃;	5.4. General procedures for the synthesis of β-carbolines 3a-d, 4a-d, 5a-d, 6a-d, 7a-d and 8a-d General procedure: A mixture of β-carboline-1-carboxaldehydes (1 mmol), diamine (1.2 mmol), anhydrous methanol (6 mL) and anhydrous CH2Cl2 (3 mL) was stirred at room temperature overnight. The solvent was evaporated under vacuum to give the crude schiff base, which was used directly in the next step without further purification.

Reference： [1]Location in patent: experimental part Chen, Zhiyong; Cao, Rihui; Shi, Buxi; Guo, Liang; Sun, Jie; Ma, Qin; Fan, Wenxi; Song, Huacan [European Journal of Medicinal Chemistry, 2011, vol. 46, # 10, p. 5127 - 5137]

65
[ 27431-62-5 ]
[ 1339939-99-9 ]
C₂₄H₃₄N₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In methanol; dichloromethane at 20℃;	5.4. General procedures for the synthesis of β-carbolines 3a-d, 4a-d, 5a-d, 6a-d, 7a-d and 8a-d General procedure: A mixture of β-carboline-1-carboxaldehydes (1 mmol), diamine (1.2 mmol), anhydrous methanol (6 mL) and anhydrous CH2Cl2 (3 mL) was stirred at room temperature overnight. The solvent was evaporated under vacuum to give the crude schiff base, which was used directly in the next step without further purification.

Reference： [1]Location in patent: experimental part Chen, Zhiyong; Cao, Rihui; Shi, Buxi; Guo, Liang; Sun, Jie; Ma, Qin; Fan, Wenxi; Song, Huacan [European Journal of Medicinal Chemistry, 2011, vol. 46, # 10, p. 5127 - 5137]

66
[ 27431-62-5 ]
[ 1339940-09-8 ]
C₂₄H₃₄N₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In methanol; dichloromethane at 20℃;	5.4. General procedures for the synthesis of β-carbolines 3a-d, 4a-d, 5a-d, 6a-d, 7a-d and 8a-d General procedure: A mixture of β-carboline-1-carboxaldehydes (1 mmol), diamine (1.2 mmol), anhydrous methanol (6 mL) and anhydrous CH2Cl2 (3 mL) was stirred at room temperature overnight. The solvent was evaporated under vacuum to give the crude schiff base, which was used directly in the next step without further purification.

Reference： [1]Location in patent: experimental part Chen, Zhiyong; Cao, Rihui; Shi, Buxi; Guo, Liang; Sun, Jie; Ma, Qin; Fan, Wenxi; Song, Huacan [European Journal of Medicinal Chemistry, 2011, vol. 46, # 10, p. 5127 - 5137]

67
[ 27431-62-5 ]
[ 203717-13-9 ]
C₂₇H₃₂N₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In methanol; dichloromethane at 20℃;	5.4. General procedures for the synthesis of β-carbolines 3a-d, 4a-d, 5a-d, 6a-d, 7a-d and 8a-d General procedure: A mixture of β-carboline-1-carboxaldehydes (1 mmol), diamine (1.2 mmol), anhydrous methanol (6 mL) and anhydrous CH2Cl2 (3 mL) was stirred at room temperature overnight. The solvent was evaporated under vacuum to give the crude schiff base, which was used directly in the next step without further purification.

Reference： [1]Location in patent: experimental part Chen, Zhiyong; Cao, Rihui; Shi, Buxi; Guo, Liang; Sun, Jie; Ma, Qin; Fan, Wenxi; Song, Huacan [European Journal of Medicinal Chemistry, 2011, vol. 46, # 10, p. 5127 - 5137]

68
[ 27431-62-5 ]
[ 6506-86-1 ]
ethyl 6-amino-4-[[4-(diethylamino)butyl]amino]-5-nitro-2-pyridinecarbamate hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
47%	In ethanol Inert atmosphere; Reflux;	4.1. Ethyl-6-amino-4-[[4-(diethylamino)-butyl]-amino]-5-nitro-2-pyridinecarbamate hydrochloride (11) 4-Diethylaminobutylamine (91 mg, 0.63 mmol) was added to a stirred solution of 3 (150 mg, 0.57 mmol) in dry ethanol (5 mL) and the resulting solution was refluxed under nitrogen atmosphere. Progress of the reaction was monitored by TLC. After the complete consumption of the starting material 3, the reaction mixture was cooled to room temperature and evaporated to dryness under reduced pressure. Diethyl ether was added drop wise to the residue and it was refrigerated for crystallization. The resulting solid was filtered and washed with ether (2 × 1 mL) and chilled ethanol (2 × 1 mL) to give 11 (110 mg, 47%) as a yellow solid. mp 178-180 °C. TLC (10% MeOH-CHCl3-1% NH4OH): Rf 0.38. 1H NMR (300 MHz, CDCl3): δ 9.18-9.10 (m, 1H, NH), 7.02 (s, 1H, NH), 6.76 (s, 1H, 5-H), 4.22 (q, 2H, J = 7.2 Hz, OCH2), 3.38 (dd, 2H, J = 6.9 Hz, 12.6 Hz, NH-CH2), 3.17-2.97 (m, 6H, 3 × NCH2), 2.00-1.95 (m, 2H, CH2), 1.84-1.78 (m, 2H, CH2), 1.40 (t, 6H, J = 6.3 Hz, 2 × CH3), 1.31 (t, 3H, J = 6.9 Hz, CH3). MS (ES) m/z (M+H)+ 369.

Reference： [1]Location in patent: experimental part Mathew, Bini; Srivastava, Shefali; Ross, Larry J.; Suling, William J.; White, E. Lucile; Woolhiser, Lisa K.; Lenaerts, Anne J.; Reynolds, Robert C. [Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 23, p. 7120 - 7128]

69
[ 27431-62-5 ]
[ 496769-48-3 ]
[ 1347750-03-1 ]

Yield	Reaction Conditions	Operation in experiment
92%	Stage #1: 4-(diethylamino)butylamine; 4,6-dichloro-2-pyrimidinyl carbamic acid ethyl ester In methanol for 3h; Inert atmosphere; Reflux; Stage #2: With ammonium hydroxide; silica gel In methanol; chloroform; water Column chromatography;	4.21. Ethyl (4-chloro-6-((5-(diethylamino)pentan-2-yl)amino)pyrimidin-2-yl)carbamate (29) General procedure: To a stirred solution of 4,6-dichloro-2-pyrimidinyl carbamic acid ethyl ester, 28 (1.0 g, 4.2 mmol) in dry methanol (20 mL), 2-amino-5-diethylaminopentane (0.84 mL, 4.2 mmol) was added. The mixture was refluxed for 3 h under nitrogen atmosphere. Excess methanol was evaporated under reduced pressure and the resulting residue was purified by silica gel column chromatography (3% MeOH-CHCl3-1% NH4OH) to afford 29 (1.22 g, 80%) as a white foam.

Reference： [1]Location in patent: experimental part Mathew, Bini; Srivastava, Shefali; Ross, Larry J.; Suling, William J.; White, E. Lucile; Woolhiser, Lisa K.; Lenaerts, Anne J.; Reynolds, Robert C. [Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 23, p. 7120 - 7128]

70
[ 27431-62-5 ]
[ 500011-87-0 ]
[ 1601472-86-9 ]

Yield	Reaction Conditions	Operation in experiment
70%	In dichloromethane at 0 - 20℃;	Common procedure for compound 8a-8l, 8n-8t. General procedure: To a solution of different amines(1-3 eq) in dichloromethane, a solution of 7(1 eq) in dichloromethane was added dropwise at 0°C. Then the resulting mixture was stirred at room temperature and monitored with TLC. The reaction mixture was evaporated to remove the most of dichloromethane. The product was obtained after recrystallization from the mixed solvent of dichloromethane and Hexane.

Reference： [1]Luo, Min; Chen, Qichao; Wang, Jin; Hu, Changyan; Lu, Jing; Luo, Xiaomin; Sun, Dequn [Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 8, p. 1987 - 1992]

71
[ 27431-62-5 ]
[ 736995-64-5 ]
[ 1601472-93-8 ]

Yield	Reaction Conditions	Operation in experiment
63%	In dichloromethane at 0 - 20℃;	Common procedure for compound 8a-8l, 8n-8t. General procedure: To a solution of different amines(1-3 eq) in dichloromethane, a solution of 7(1 eq) in dichloromethane was added dropwise at 0°C. Then the resulting mixture was stirred at room temperature and monitored with TLC. The reaction mixture was evaporated to remove the most of dichloromethane. The product was obtained after recrystallization from the mixed solvent of dichloromethane and Hexane.

Reference： [1]Luo, Min; Chen, Qichao; Wang, Jin; Hu, Changyan; Lu, Jing; Luo, Xiaomin; Sun, Dequn [Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 8, p. 1987 - 1992]

72
[ 27431-62-5 ]
2-(((2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl)thio)-benzoyl chloride [ No CAS ]
[ 1402249-35-7 ]

Yield	Reaction Conditions	Operation in experiment
76%	With triethylamine In dichloromethane at 0℃; for 0.5h;

Reference： [1]Ling, Yong; Wang, Xuemin; Zhu, Hongyan; Wang, Zhiqiang; Xu, Chenjun; Wang, Xinyang; Chen, Li; Zhang, Wei [Archiv der Pharmazie, 2014, vol. 347, # 5, p. 327 - 333]

73
[ 27431-62-5 ]
2,2,2-trifluoro-N-[(2-formylpyridin-4-yl)methyl]acetamide [ No CAS ]
[ 56553-60-7 ]
N-[2-([4-(diethylamino)butyl]amino}methyl)pyridin-4-yl]methyl}-2,2,2-trifluoroacetamide acetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 4-(diethylamino)butylamine; 2,2,2-trifluoro-N-[(2-formylpyridin-4-yl)methyl]acetamide In 1,2-dichloro-ethane at 20℃; for 2h; Inert atmosphere; Stage #2: sodium tris(acetoxy)borohydride In 1,2-dichloro-ethane at 20℃;	1.A General Procedure A (Reductive Amination) General procedure: General Procedure A (Reductive Amination) A solution of aldehyde (2,2,2-trifluoro-N-[(2-formylpyridin-4-yl)methyl]acetamide) and amine ((4- aminobutyl)diethylamine) (1.3 equiv.) in 1,2-dichloroethane was stirred for 2h at room temperature, before NaBH(AcO)3 (2 eq) was added. The mixture was stirred overnight at room temperature. The solvents were removed in vacuo and the residue was purified by preparative TLC (40% MeOH in DCM) . The title product was isolated as colorless oil as the acetate salt. 1H NMR (300 MHz, CD3OD) δ ppm : 8.57 (d, IH), 7.38 (s, IH), 7.29 (d, IH), 4.53 (s, 2H), 4.13 (s, 2H), 3.13 (q, 4H), 3.04 (t, 2H), 2.91 (t, 2H), 1.94 (s, 6H), 1.77 (m, 4H), 1.25 (t, 6H). ES-MS: 361 [M + H] . Method A - Reductive amination Compounds of Formula (I) may be prepared from 4-formyl pyridines according to Scheme 1, where R' is a suitable protecting group or R1, in one-pot or by a stepwise procedure by mixing with an amine, optionally containing orthogonal protected reactive sites, and a reducing agent such as NaBH4, NaBH(OAc)3, NaCNBH3, or Et3SiH, either at room temperature or by heating for up to several hours by use of a solvent such as an alcohol, DCE, DCM, water, or toluene, optionally adding a catalyst such as an acid or a Lewis acid. Optionally, protecting groups may be removed and a purification method such as silica gel chromatography is employed if needed.

Reference： [1]Current Patent Assignee: GILEAD SCIENCES INC - WO2014/131777, 2014, A1 Location in patent: Page/Page column 45; 102

74
[ 27431-62-5 ]
tert-butyl N-(4-[2-[6-(2-chlorophenyl)-2-methanesulfonyl-7-oxo-7H, 8H-pyrido[2,3-d]pyrimidin-8-yl]ethyl]phenyl)carbamate [ No CAS ]
tert-butyl N-(4-[2-[6-(2-chlorophenyl)-2-[[4-(diethylamino)butyl]amino]-7-oxo-7H,8H-pyrido[2,3-d]pyrimidin-8-yl] ethyl]phenyl)carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine at 80℃; for 2h;	1.3 Into a 250-mi. round-bottom flask, was placed tert-butyl N-(4-[2-[6-(2-chlorophenyl)-2-methanesulfonyl-7-oxo-7H, 8H-pyrido [2,3 -d]pyrimidin-8-yl]ethyl]phenyl)carbamate (3.20 g,5.77 mmol, 1.00 equiv), (4-aminobutyl)diethylamine (1.67 g, 11.58 mmol, 2.00 equiv), pyridine(40 mL). The resulting solution was stirred for 2 h at 80° C in an oil bath. The resulting mixturewas concentrated under vacuum. The residue was applied onto a silica gel colunm withmethanol:EtOAc (EtOAc-1 :30-1:20) . The collected fractions were combined and concentrated under vacuum. This resulted in 2.80 g (crude) of tert-butyl N-(4-[2-[6-(2-chlorophenyl)-2-[[4- (diethylamino)butyl] amino]-7-oxo-7H, 8H-pyrido [2,3 -d]pyrimidin-8-yl] ethyl]phenyl)carbamate as a brown solid.
	With pyridine at 80℃; for 2h;	1.3 Step 3 Into a 250-mL round-bottom flask, was placed tert-butyl N-(4-[2-[6-(2-chlorophenyl)-2- methanesulfonyl-7-oxo-7H,8H-pyrido[2,3-d]pyrimidin-8-yl]ethyl]phenyl)carbamate (3.20 g, 5.77 mmol, 1.00 equiv), (4-aminobutyl)diethylamine (1.67 g, 11.58 mmol, 2.00 equiv) and pyridine (40 mL). The resulting solution was stirred for 2 h at 80° C and then concentrated under vacuum. The residue was purified by silica gel column with methanol: ethyl acetate (EA-1 :30- 1 :20) to give 2.80 g (crude) of tert-butyl N-(4-[2-[6-(2-chlorophenyl)-2-[[4- (diethylamino)butyl]amino]-7-oxo-7H,8H-pyrido[2,3-d]pyrimidin-8-yl]ethyl]phenyl)-carbamate as a brown solid.

Reference： [1]Current Patent Assignee: SANOFI - WO2014/182829, 2014, A1 Location in patent: Page/Page column 44
[2]Current Patent Assignee: SANOFI - WO2016/191172, 2016, A1 Location in patent: Page/Page column 70

75
[ 27431-62-5 ]
6-(2-fluoro-3,5-dimethoxyphenyl)-2-methanesulfonyl-8-[2-(3-nitrophenyl)ethyl]-7H,8H-pyrido[2,3-d]pyrimidin-7-one [ No CAS ]
2-[[4-(diethylamino)butyl]amino]-6-(2-fluoro-3,5-dimethoxyphenyl)-8-[2-(3-nitrophenyl)ethyl]-7H,8H-pyrido[2,3-d]pyrimidin-7-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With triethylamine In 2-methyl-propan-1-ol at 55℃;	42.3 A solution of 6-(2-fluoro-3 ,5 -dimethoxyphenyl)-2-methanesulfonyl-8- [2-(3 - nitrophenyl)ethyl]-7H, 8H-pyrido [2,3 -d]pyrimidin-7-one (420 mg, 0.79 mmol), TEA (250 mg, 2.47 mmol) and (4-aminobutyl)diethylamine (115 mg, 0.80 mmol) in 2-methylpropan-2-ol (50 mL) was stirred overnight at 55 °C. The resulting solution was diluted with water and extractedwith DCM/MeOH(10:1). The organic layer was concentrated to afford 400mg (85%) of 2-[[4-(diethylamino)butyl] amino] -6-(2-fluoro-3 ,5 -dimethoxyphenyl)-8- [2-(3 -nitrophenyl)ethyl] -7H, 8H-pyrido [2,3 -d]pyrimidin-7-one as a yellow solid.

Reference： [1]Current Patent Assignee: SANOFI - WO2014/182829, 2014, A1 Location in patent: Page/Page column 91

76
[ 27431-62-5 ]
tert-butyl 3-(2-(6-(2-chlorophenyl)-2-(methylsulfonyl)-7-oxopyrido[2,3-d]pyrimidin-8(7H)-yl)ethyl)piperidine-1-carboxylate [ No CAS ]
tert-butyl 3-(2-(6-(2-chlorophenyl)-2-(4-(diethylamino)butylamino)-7-oxopyrido[2,3-d]pyrimidin-8(7H)-yl)ethyl)piperidine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%	With pyridine at 80℃; for 2h;	2.3 Step 3 A solution of tert-butyl 3-(2-(6-(2-chlorophenyl)-2-(methylsulfonyl)-7-oxopyrido[2,3-d]- pyrimidin-8(7H)-yl)ethyl)piperidine-l-carboxylate (3.27 g, 6 mmol, 1.0 equiv) and N1, N1- diethylbutane-l,4-diamine (2.6 g, 18 mmol, 3.0 equiv) in pyridine (20 mL) was heated to 80° C for 2 hours. The mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated under vacuum. The residue was purified by column chromatography using ethyl acetate/methanol (30/1 to 5/1) to give 2.2 g (60%) of tert-butyl 3-(2-(6-(2-chlorophenyl)-2-(4- (diethylamino)butylamino)-7-oxopyrido[2,3-d]pyrimidin-8(7H)-yl)ethyl)piperidine-l- carboxylate as a brown solid.
2.2 g	With pyridine at 80℃; for 2h;	2.3 A solution of tert-butyl 3 -(2-(6-(2-chlorophenyl)-2-(methylsulfonyl)-7-oxopyrido [2,3 -d] -pyrimidin-8(7H)-yl)ethyl)piperidine-1-carboxylate (3.27 g, 6 mmol, 1.0 equiv) and N’, N’diethylbutane-1, 4-diamine (2.6 g, 18 mmol, 3.0 equiv) in Py (20 mL) was heated to 80° C for 2The mixture was poured into water and extracted with EtOAc. The organic layer was washed with brine, dried over anhydrous sodium sulfate. The solids were filtered and concentrated under vacuum. The residue was purified by column chromatography using EtOAc/MeOH (30/1 to 5/1). This resulted in 2.2 g (60%) of tert-butyl 3-(2-(6-(2-chlorophenyl)-2-(4-(diethylamino)butyl- amino)-7-oxopyrido [2,3 -d]pyrimidin-8(7H)-yl)ethyl)piperidine- 1 -carboxylate as a brown solid.

Reference： [1]Current Patent Assignee: SANOFI - WO2016/191172, 2016, A1 Location in patent: Page/Page column 72
[2]Current Patent Assignee: SANOFI - WO2014/182829, 2014, A1 Location in patent: Page/Page column 45; 46

77
[ 27431-62-5 ]
tert-butyl N-(4-[2-[6-(2,6-dichloro-3,5-dimethoxyphenyl)-2-methanesulfonyl-7-oxo-7H,8H-pyrido[2,3-d]pyrimidin-8-yl]ethyl]phenyl)carbamate [ No CAS ]
tert-butyl N-(4-[2-[6-(2,6-dichloro-3,5-dimethoxyphenyl)-2-[[4-(diethylamino)butyl]amino]-7-oxo-7H,8H-pyrido[2,3-d]pyrimidin-8-yl]ethyl]phenyl)carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
98%	With triethylamine In dimethyl sulfoxide at 50℃; for 4h;	5.1 Into a 100-mi. round-bottom flask, was placed a solution of tert-butyl N-(4-[2-[6-(2,6-dichloro-3 ,5 -dimethoxyphenyl)-2-methanesulfonyl-7-oxo-7H,8H-pyrido [2,3 -d]pyrimidin-8-yl]ethyl]phenyl)carbamate (1.02 g, 1.57 mmol, 1.00 equiv) in DMSO (30 mL). TEA (477 mg, 4.71 mmol, 3.00 equiv) and (4-aminobutyl)diethylamine (340 mg, 2.36 mmol, 1.50 equiv) were added and the resulting solution was stirred for 4 h at 50° C, and then it was diluted with water. The resulting solution was extracted with ethyl acetate, and the combined organic layers werewashed with brine and concentrated under vacuum. This resulted in 1.1 g (98%) of tert-butyl N(4-[2- [6-(2,6-dichloro-3 ,5 -dimethoxyphenyl)-2- [ [4-(diethylamino)butyl]amino] -7-oxo-7H,8H-pyrido[2,3-d]pyrimidin-8-yl]ethyl]phenyl)carbamate as a brown solid which was converted to 8-[2-(4-aminophenyl)ethyl] -6-(2,6-dichloro-3 ,5 -dimethoxyphenyl)-2-[ [4-(diethylamino)butyl] - amino]-7H,8H-pyrido[2,3-d]pyrimidin-7-one under conditions similar to those described in Example 4, Step 9 above.
98%	With triethylamine In dimethyl sulfoxide at 50℃; for 4h;	4.3 Step 3 Into a 100-mL round-bottom flask, was placed a solution of tert-butyl N-(4-[2-[6-(2,6- dichloro-3,5-dimethoxyphenyl)-2-methanesulfonyl-7-oxo-7H,8H-pyrido[2,3-d]pyrimidin-8-yl]- ethyl]phenyl)carbamate (1.02 g, 1.57 mmol, 1.00 equiv) in DMSO (30 mL). TEA (477 mg, 4.71 mmol, 3.00 equiv) and (4-aminobutyl)diethylamine (340 mg, 2.36 mmol, 1.50 equiv) were added to the reaction mixture. The resulting solution was stirred for 4 h at 50° C, and then it was diluted with water. The resulting solution was extracted with ethyl acetate, and the combined organic layers were washed with brine and concentrated under vacuum. This resulted in 1.1 g (98%) of tert-butyl N-(4-[2-[6-(2,6-dichloro-3,5-dimethoxy-phenyl)-2-[[4- (diethylamino)butyl]amino]-7-oxo-7H,8H-pyrido[2,3-d]pyrimidin-8-yl]ethyl]-phenyl)carbamate as a brown solid.

Reference： [1]Current Patent Assignee: SANOFI - WO2014/182829, 2014, A1 Location in patent: Page/Page column 51; 52
[2]Current Patent Assignee: SANOFI - WO2016/191172, 2016, A1 Location in patent: Page/Page column 75

78
[ 27431-62-5 ]
tert-butyl N-(3-[[6-(2,6-dichloro-3,5-dimethoxyphenyl)-2-methanesulfonyl-7-oxo-7H,8H-pyrido[2,3-d]pyrimidin-8-yl]methyl]phenyl)carbamate [ No CAS ]
tert-butyl N-(3-[[6-(2,6-dichloro-3,5-dimethoxyphenyl)-2-[[4-(diethylamino)butyl]amino]-7-oxo-7H,8H-pyrido[2,3-d]pyrimidin-8-yl]methyl]phenyl)carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
100%	With triethylamine In dimethyl sulfoxide at 50℃; for 5h;	6.5 Into a 50-mi. round-bottom flask, was placed a solution of tert-butyl N-(3-[[6-(2,6- dichloro-3 ,5 -dimethoxyphenyl)-2-methanesulfonyl-7-oxo-7H,8H-pyrido [2,3 -d]pyrimidin-8- yl]methyl]phenyl)carbamate (360 mg, 0.S7 mmol, 1.00 equiv) in DMSO (30 mL). (4-Aminobutyl)diethylamine (122.6 mg, 0.8S mmol, 1.50 equiv) and triethylamine (172.4 mg, 1.70 mmol, 3.00 equiv) were added to the reaction mixture. The resulting solution was stirred for S h at S0° C, and then it was quenched with water. The resulting solution was extracted with ethyl acetate, and the combined organic layers were dried over anhydrous sodium sulfate and concentrated under vacuum. This resulted in 396 mg (100%) of tert-butyl N-(3-[[6-(2,6- dichloro-3 ,5 -dimethoxyphenyl)-2-[ [4-(diethylamino)butyl] amino] -7-oxo-7H,8H-pyrido [2,3 -d]pyrimidin-8-yl]methyl]phenyl)carbamate as a yellow solid.

Reference： [1]Current Patent Assignee: SANOFI - WO2014/182829, 2014, A1 Location in patent: Page/Page column 53; 54

79
[ 27431-62-5 ]
tert-butyl N-(3-[2-[6-(2,6-dichloro-3,5-dimethoxyphenyl)-2-methanesulfonyl-7-oxo-7H,8H-pyrido[2,3-d]pyrimidin-8-yl]ethyl]phenyl)carbamate [ No CAS ]
tert-butyl N-(3-[2-[6-(2,6-dichloro-3,5-dimethoxyphenyl)-2-[[4-(diethylamino)butyl]amino]-7-oxo-7H,8H-pyrido[2,3-d]pyrimidin-8-yl]ethyl]phenyl)carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
96%	With triethylamine In dimethyl sulfoxide at 50℃;	7.6 General procedure: Into a 50-mi. round-bottom flask, was placed a solution of tert-butyl N-(4-[2-[6-(2,6- dichloro-3 ,5 -dimethoxyphenyl)-2-methanesulfonyl-7-oxo-7H,8H-pyrido [2,3 -d]pyrimidin-8- yl]ethyl]phenyl)carbamate (160 mg, 0.25 mmol, 1.00 equiv) in DMSO (5 mL). TEA (124.6 mg,1.23 mmol, 5.00 equiv), and methanamine hydrochloride (33.4 mg, 0.49 mmol, 2.00 equiv) were added and the resulting solution was stirred overnight at 500 C, and then it was diluted with H20. The resulting solution was extracted with ethyl acetate, and the combined organic layers were washed with brine, concentrated under vacuum to give 120 mg (8 1%) of tert-butyl N-(4-[2-[6- (2,6-dichloro-3 ,5 -dimethoxyphenyl)-2-(methylamino)-7-oxo-7H, 8H-pyrido [2,3 -d]pyrimidin-8-yl]ethyl]phenyl)carbamate as a brown solid. Proceeding under conditions similar to those described in Example 4, Step 8 above, tertbutyl N-(3 -[2- [6-(2,6-dichloro-3 ,5 -dimethoxyphenyl)-2-methanesulfonyl-7-oxo-7H, 8H-pyrido[2,3-d]pyrimidin-8-yl]ethyl]-phenyl)carbamate (400 mg) was converted to tert-butyl N--[2- [6-(2,6-dichloro-3 ,5 -dimethoxyphenyl)-2- [ [4-(diethylamino)butyl]amino] -7-oxo-7H,8H- pyrido[2,3-d]pyrimidin-8-yl]ethyl]phenyl)carbamate 420 mg (96%) as a brown solid by substituting methamine with (4-aminobutyl)diethylamine.

Reference： [1]Current Patent Assignee: SANOFI - WO2014/182829, 2014, A1 Location in patent: Page/Page column 50; 56

80
[ 27431-62-5 ]
[ 1493-27-2 ]
C₁₄H₂₃N₃O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In tetrahydrofuran at 30℃; for 12h; Inert atmosphere;	12 5.1.1 General procedure for the preparation of intermediate 2a-1∼2a-6, 2b-1∼2b-6, 2c-1∼2c-2, 2e-1∼2e-3, 2g-1∼2g-2 General procedure: Compound 1 (20 mmol) and proper amine (20 mmol) were dissolved in tetrahydrofuran, and the reaction mixture was stirred at 30 °C for 12 h under nitrogen. After completion of the reaction, the mixture was then extracted with dichloromethane after evaporating the tetrahydrofuran, washed with water, and concentrated to provide crude oil product. The residue was used for next synthetic step without further purification.

Reference： [1]Yao, Bing-Lei; Mai, Yan-Wen; Chen, Shuo-Bin; Xie, Hua-Ting; Yao, Pei-Fen; Ou, Tian-Miao; Tan, Jia-Heng; Wang, Hong-Gen; Li, Ding; Huang, Shi-Liang; Gu, Lian-Quan; Huang, Zhi-Shu [European Journal of Medicinal Chemistry, 2015, vol. 92, p. 540 - 553]

81
[ 27431-62-5 ]
N-(7-chloroquinolin-4-yl)-ethanethioamide [ No CAS ]
(Z)-N-(7-chloroquinolin-4-yl)-N′-[4-(diethylamino)-butyl]-acetimidamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86.2%	With triethylamine; mercury(II) oxide In N,N-dimethyl-formamide at 20℃;

Reference： [1]Korotchenko, Vasiliy; Sathunuru, Ramadas; Gerena, Lucia; Caridha, Diana; Li, Qigui; Kreishman-Deitrick, Mara; Smith, Philip L.; Lin, Ai J. [Journal of Medicinal Chemistry, 2015, vol. 58, # 8, p. 3411 - 3431]

82
[ 27431-62-5 ]
N-(7-chloro-quinolin-4yl)-2-methylpropanethioamide [ No CAS ]
(Z)-N-(7-chloroquinolin-4-yl)-N′-(4-diethylaminobutyl)-isobutyrimidamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
98%	With triethylamine; mercury(II) oxide In N,N-dimethyl-formamide at 20℃;

Reference： [1]Korotchenko, Vasiliy; Sathunuru, Ramadas; Gerena, Lucia; Caridha, Diana; Li, Qigui; Kreishman-Deitrick, Mara; Smith, Philip L.; Lin, Ai J. [Journal of Medicinal Chemistry, 2015, vol. 58, # 8, p. 3411 - 3431]

83
[ 27431-62-5 ]
[ 623903-29-7 ]
2-(3-(((4-(diethylamino)butyl)imino)methyl)-1H-indol-2-yl)quinazolin-4(3H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
48%	With iron(III) chloride; magnesium sulfate In chloroform at 20℃; for 6h;

Reference： [1]Rao, Yong; Liu, Hong; Gao, Lin; Yu, Hong; Ou, Tian-Miao; Tan, Jia-Heng; Huang, Shi-Liang; Wang, Hong-Gen; Li, Ding; Gu, Lian-Quan; Ye, Ji-Ming; Huang, Zhi-Shu [Journal of Medicinal Chemistry, 2015, vol. 58, # 23, p. 9395 - 9413]

84
[ 27431-62-5 ]
C₁₅H₅Cl₂N₇ [ No CAS ]
C₂₃H₂₄ClN₉ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	With triethylamine In N,N-dimethyl-formamide at 60℃;

Reference： [1]Li, Peng-Hui; Zeng, Ping; Chen, Shuo-Bin; Yao, Pei-Fen; Mai, Yan-Wen; Tan, Jia-Heng; Ou, Tian-Miao; Huang, Shi-Liang; Li, Ding; Gu, Lian-Quan; Huang, Zhi-Shu [Journal of Medicinal Chemistry, 2016, vol. 59, # 1, p. 238 - 252]

85
[ 27431-62-5 ]
5-[(1H-benzoimidazol-2-yl)-cyano-methyl]-6-chloro-pyrazine-2,3-dicarbonitrile [ No CAS ]
6-amino-7-(1H-benzo[d]imidazol-2-yl)-5-(4-(diethylamino)butyl)-5H-pyrrolo[2,3-b]pyrazine-2,3-dicarbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%	With triethylamine In N,N-dimethyl-formamide at 60℃;

Reference： [1]Li, Peng-Hui; Zeng, Ping; Chen, Shuo-Bin; Yao, Pei-Fen; Mai, Yan-Wen; Tan, Jia-Heng; Ou, Tian-Miao; Huang, Shi-Liang; Li, Ding; Gu, Lian-Quan; Huang, Zhi-Shu [Journal of Medicinal Chemistry, 2016, vol. 59, # 1, p. 238 - 252]

86
[ 27431-62-5 ]
C₁₅H₅ClN₆O [ No CAS ]
6-amino-7-(benzo[d]oxazol-2-yl)-5-(4-(diethylamino)butyl)-5H-pyrrolo[2,3-b]pyrazine-2,3-dicarbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
43%	With triethylamine In N,N-dimethyl-formamide at 60℃;

Reference： [1]Li, Peng-Hui; Zeng, Ping; Chen, Shuo-Bin; Yao, Pei-Fen; Mai, Yan-Wen; Tan, Jia-Heng; Ou, Tian-Miao; Huang, Shi-Liang; Li, Ding; Gu, Lian-Quan; Huang, Zhi-Shu [Journal of Medicinal Chemistry, 2016, vol. 59, # 1, p. 238 - 252]

87
[ 27431-62-5 ]
5-chloro-6-[cyano-(1-methyl-1H-benzoimidazol-2-yl)-methyl]-pyrazine-2,3-dicarbonitrile [ No CAS ]
6-amino-5-(4-(diethylamino)butyl)-7-(1-methyl-1H-benzo[d]imidazol-2-yl)-5H-pyrrolo[2,3-b]pyrazine-2,3-dicarbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	With triethylamine In N,N-dimethyl-formamide at 60℃;

Reference： [1]Li, Peng-Hui; Zeng, Ping; Chen, Shuo-Bin; Yao, Pei-Fen; Mai, Yan-Wen; Tan, Jia-Heng; Ou, Tian-Miao; Huang, Shi-Liang; Li, Ding; Gu, Lian-Quan; Huang, Zhi-Shu [Journal of Medicinal Chemistry, 2016, vol. 59, # 1, p. 238 - 252]

88
[ 27431-62-5 ]
[ 43091-89-0 ]
4-[4-(diethylamino)butylamino]-6,7-dimethoxy-1H-quinazoline-2-thione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%	With triethylamine In tetrahydrofuran at 150℃; for 0.75h; Microwave irradiation;

Reference： [1]Robaa, Dina; Wagner, Tobias; Luise, Chiara; Carlino, Luca; McMillan, Joel; Flaig, Ralf; Schüle, Roland; Jung, Manfred; Sippl, Wolfgang [ChemMedChem, 2016, vol. 11, # 20, p. 2327 - 2338]

Type	HazMat fee for 500 gram (Estimated)
Excepted Quantity	USD 0.00
Limited Quantity	USD 15-60
Inaccessible (Haz class 6.1), Domestic	USD 80+
Inaccessible (Haz class 6.1), International	USD 150+
Accessible (Haz class 3, 4, 5 or 8), Domestic	USD 100+
Accessible (Haz class 3, 4, 5 or 8), International	USD 200+

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 -

CAS No. :	27431-62-5	MDL No. :	MFCD00014836
Formula :	C₈H₂₀N₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	JILXUIANNUALRZ-UHFFFAOYSA-N
M.W :	144.26	Pubchem ID :	117976
Synonyms :

Signal Word:	Danger	Class:	8
Precautionary Statements:	P280-P305+P351+P338-P310	UN#:	2735
Hazard Statements:	H314	Packing Group:	Ⅲ
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. 27431-62-5 ] {[proInfo.proName]}

Quality Control of [ 27431-62-5 ]

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Product Details of [ 27431-62-5 ]

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Application In Synthesis of [ 27431-62-5 ]

[ 27431-62-5 ] Synthesis Path-Downstream 1~88

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry