39903-01-0|2-Amino-5-bromo-3-pyridinol| Ambeed

Structure of 39903-01-0

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Quality Control of [ 39903-01-0 ] Purity: 98% SDS Specification

COA

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NMR

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Product Details of [ 39903-01-0 ]

CAS No. :	39903-01-0
Formula :	C₅H₅BrN₂O
M.W :	189.01
SMILES Code :	NC1=NC=C(C=C1O)Br
MDL No. :	MFCD09744143
InChI Key :	YQADLKDQAXAIKW-UHFFFAOYSA-N
Pubchem ID :	11694041

Safety of [ 39903-01-0 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Computational Chemistry of [ 39903-01-0 ] Show Less

Physicochemical Properties

Num. heavy atoms	9
Num. arom. heavy atoms	6
Fraction Csp3	0.0
Num. rotatable bonds	0
Num. H-bond acceptors	2.0
Num. H-bond donors	2.0
Molar Refractivity	38.36
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	59.14 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.25
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	0.84
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.14
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	0.37
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	0.91
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	0.9

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.03
Solubility	1.75 mg/ml ; 0.00924 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-1.66
Solubility	4.09 mg/ml ; 0.0216 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-1.95
Solubility	2.15 mg/ml ; 0.0114 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	Yes
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	No
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-6.86 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	1.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	0.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<1.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	1.76

Application In Synthesis of [ 39903-01-0 ]

* 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 [ 39903-01-0 ]

[ 39903-01-0 ] Synthesis Path-Downstream 1~55

1
[ 21594-52-5 ]
[ 39903-01-0 ]

Yield	Reaction Conditions	Operation in experiment
98%	With sodium hydroxide; water;Heating / reflux;	2: 6-Bromo-3H-oxazolo[4,5-b]pyridin-2-one (21.5 g, 100 mmol) was suspended in NaOH solution (2N, 250 mL, 500 mmol). The mixture was refluxed overnight and a clear solution was obtained. After cooling to room temperature, the reaction solution was neutralized to pH ~7. A lot of CO2 was released and also precipitate was observed. The product was filtered, washed with water, and dried under high vacuum to provide 2-amino-5-bromo-pyridin-3-ol as an off-white solid (17.8 g, 98percent yield).
98%		6-Bromo-3H-oxazolo[4,5-b]pyridin-2-one (21.5 g, 100 mmol) was suspended in NaOH solution (2N, 250 mL, 500 mmol). The mixture was refluxed overnight and a clear solution was obtained. After cooling to room temperature, the reaction solution was neutralized to pH ~7. A lot of C02 was released and also precipitate was observed. The product was filtered, washed with water, and dried under high vacuum to provide 2-amino-5-bromo-pyridin-3-ol as an off-white solid (17.8 g, 98percent yield).
80 - 93%		To a solution of 6-bromo-3H-oxazolo[4,5-.pound.]pyridin-2-one (28.0 g, 130 mmol) in MeOH (280 mL) was added a solution of NaOH (28.1 g, 703 mmol) in water (280 mL). The mixture was heated to reflux overnight. The organic solvent was removed in vacuo and the aqueous mixture was adjusted to peta 5-6 with 12 M HCl. The resulting precipitate was isolated by filtration, washed with Et2psi and dried under vacuum at 50 °C overnight to give the title compound (19.6 g, 80percent) as a gray solid: 1H NMR (500 MHz, DMSO-cfc) delta 10.1 (s, IH), 7.46 (d, J= 1.5 Hz, IH), 6.88 (s, IH), 5.70 (s, 2H); ESI MS m/z 190 (M + H)+.; To a suspension of 6-bromo-3H-oxazolo[4,5-]pyridin-2-one (20.0 g, 93.0 mmol) in methanol (200 mL) was added NaOH (20.0 g, 500 mmol) in H2O (200 mL) and the mixture was heated to reflux overnight. After cooling, methanol was removed in vacuo. The aqueous residue was acidified with 3N HCl to pH 5-6. The resulting precipitate was collected by filtration, and dried overnight under vacuum at 45 0C to give the title compound as a tan solid (16.4 g, 93percent): 1H NMR (300 MHz, DMSO-^) delta 10.03 (s, IH), 7.47 (d, J= 2.0 Hz, IH), 6.93 (d, J= 2.0 Hz, IH), 5.72 (s, 2H); ESI MS m/e 188 (M + H)+.

80%		[00104] As shown in step 4-iii of Scheme 20, Compound 1012 (34 g, 158.1 mmol) was diluted with 10percent NaOEta(aq) (500 mL), and the resulting mixture was stirred at 100 0C for 6 h. The reaction was cooled to 5 0C, and 6 N HCl was added until a precipitate formed (ca. pH 10). The solid was collected in a fritted funnel, washed with water (200 mL), and dried under vacuum to afford 2-amino-5-bromo-3-hydroxypyridine (Compound 1013, 24.0 g, 80percent yield) as a tan solid: ESMS (M+H) 189, 191; 1H NMR (DMSO-d6) delta 7.5 (s, IH), 6.9 (s, IH), 5.7 (br, 2H).
80%		As shown in step 4-iii of Scheme 20, Compound 1012 (34 g, 158.1 mmol) was diluted with 10percent NaOEta(aq) (500 mL), and the resulting mixture was stirred at 100 0C for 6 h. The reaction was cooled to 5 0C, and 6 N HCl was added until a precipitate formed (ca. pH 10). The solid was collected in a fritted funnel, washed with water (200 mL), and dried under vacuum to afford 2-amino-5-bromo-3-hydroxypyridine (Compound 1013, 24.0 g, 80percent yield) as a tan solid: ESMS (M+H) 189, 191; 1H NMR (DMSO-d6) delta 7.5 (s, IH), 6.9 (s, IH), 5.7 (br, 2H).
	With water; sodium hydroxide; for 4h;Reflux;	6-bromo[1 ,3]oxazolo[4,5-o]pyridin-2(3H)-one (I-52) (69 g, 0.3 mol) was added to 10percent aqueous sodium hydroxide (600 ml_) and the mixture was refluxed for 4 h. TLC (EtOAc/hexane= 1 :2) indicated the reaction was complete. The mixture was cooled to room temperature and acidified to pH~7 by dropwise addition of 10percent HCI (300 mL). The precipitate formed was filtered, washed with water (100 mL) and dried undervacuum to afford 2-amino-5-bromopyridin-3-ol (I-53) (58 g, 73percent) as a yellow solid, which was used without further purification.

References: [1]Patent: US2006/46991,2006,A1 .Location in patent: Page/Page column 33-34.
[2]Patent: WO2006/21886,2006,A1 .Location in patent: Page/Page column 64; 65.
[3]Heterocycles,2001,vol. 55,p. 1329 - 1345.
[4]Heterocycles,1995,vol. 41,p. 2799 - 2810.
[5]Tetrahedron Letters,2014,vol. 55,p. 1528 - 1531.
[6]Patent: WO2007/67416,2007,A2 .Location in patent: Page/Page column 56; 57; 92; 95.
[7]Patent: WO2010/96389,2010,A1 .Location in patent: Page/Page column 42-43; 44.
[8]Patent: WO2010/135014,2010,A1 .Location in patent: Page/Page column 50-51.
[9]Patent: WO2016/97918,2016,A1 .Location in patent: Page/Page column 66.

2
[ 39903-01-0 ]
[ 65-85-0 ]
[ 174469-41-1 ]

References: [1]Heterocycles,1995,vol. 41,p. 2799 - 2810.

Yield	Reaction Conditions	Operation in experiment
		L. 2-Amino-5-bromo-3-pyridinol 6-Bromooxazolo[4,5-b]pyridine-2(3H)-one (K. Rufenacht and H. Kristinsson, Helv. Chim. Acta 59 (5), 1953 [1976]) (4.3 g; 0.02 mole) sodium hydroxide (5 g; 0.125 mole) and water (50 ml) were stirred on the steam bath for 45 minutes. The solution was cooled to approximately 10° C. and carefully acidified with concentrated HCl (considerable foaming). The resulting solid was collected by filtration, washed with water and dried. The yield was 3.0 g (79 percent) of tan solid melting at 187° to 189° C. Recrystallization from aqueous ethanol afforded 2.0 g of tan crystals, melting point 195° to 197° C. Analysis calculated for C5 H5 BrN2 O: C, 37.77; H, 2.67; N, 14.82; Br, 42.27. Found: C, 37.76; H, 2.79; N, 14.87; Br, 41.94.

4
[ 1822-32-8 ]
[ 39903-01-0 ]
[ 364385-46-6 ]

References: [1]Heterocycles,2001,vol. 55,p. 1329 - 1345.

5
[ 619-65-8 ]
[ 39903-01-0 ]
[ 364385-30-8 ]

References: [1]Heterocycles,2001,vol. 55,p. 1329 - 1345.

6
[ 39903-01-0 ]
[ 130927-83-2 ]
[ 364385-38-6 ]

References: [1]Heterocycles,2001,vol. 55,p. 1329 - 1345.

7
[ 39903-01-0 ]
[ 339333-00-5 ]
[ 364385-39-7 ]

References: [1]Heterocycles,2001,vol. 55,p. 1329 - 1345.

8
[ 39903-01-0 ]
[ 51052-78-9 ]
[ 364385-45-5 ]

References: [1]Heterocycles,2001,vol. 55,p. 1329 - 1345.

9
[ 14002-80-3 ]
[ 39903-01-0 ]
[ 1003023-47-9 ]

Yield	Reaction Conditions	Operation in experiment
39%	With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 0 - 120℃; for 0.333333h;Microwave irradiation;	To a suspension of <strong>[39903-01-0]2-amino-5-bromopyridin-3-ol</strong> (1.42 g, 7.51 mmol) in THF (40 mL) was added methyl 2,2-dimethyl-3-hydroxypropionate (1.2 mL, 9.0 mmol) and triphenyl phosphine (2.36 g, 9.00 mmol). The mixture was cooled to 0 0C, then treated with diethyl diazodicarboxylate (1.70 g, 9.75 mmol). The mixture was heated in microwave at 120 0C for 20 min. The solvent was concentrated, and the residue was purified by chromatography (silica gel, hexanes/EtOAc, 75:25 to 60:40) to give the title compound (0.88 g, 39percent) as a white solid: 1H NMR (300 MHz, CDCl3) delta 7.73 (d, J= 2.1 Hz, IH), 7.02 (d, J= 2.1 Hz, IH), 4.65 (br s, 2H), 3.96 (s, 2H), 3.71 (s, 3H), 1.34 (s, 6H); ESI MS m/e 303 (M + H)+. b) 3-Bromo-7,7-dimethyl-6,7-dihydro-9H-5-oxa-l,9-diaza-benzocyclohepten-8- one

References: [1]Patent: WO2008/9122,2008,A1 .Location in patent: Page/Page column 69.

10
[ 60832-72-6 ]
[ 39903-01-0 ]

References: [1]Heterocycles,2001,vol. 55,p. 1329 - 1345.
[2]Heterocycles,1995,vol. 41,p. 2799 - 2810.
[3]Tetrahedron Letters,2014,vol. 55,p. 1528 - 1531.
[4]Patent: WO2016/97918,2016,A1 .

11
[ 39903-01-0 ]
[ 364385-32-0 ]

References: [1]Heterocycles,2001,vol. 55,p. 1329 - 1345.

12
[ 39903-01-0 ]
[ 364385-31-9 ]

References: [1]Heterocycles,2001,vol. 55,p. 1329 - 1345.

13
[ 39903-01-0 ]
[ 364385-34-2 ]

References: [1]Heterocycles,2001,vol. 55,p. 1329 - 1345.

14
[ 39903-01-0 ]
[ 364385-47-7 ]

References: [1]Heterocycles,2001,vol. 55,p. 1329 - 1345.

15
[ 39903-01-0 ]
methyl 3-{2-[2-(4-piperidinyl)ethyl]oxazolo[4,5-b]pyridin-6-yl}propanoate [ No CAS ]

References: [1]Heterocycles,2001,vol. 55,p. 1329 - 1345.
[2]Heterocycles,2001,vol. 55,p. 1329 - 1345.

16
[ 39903-01-0 ]
[ 364385-48-8 ]

References: [1]Heterocycles,2001,vol. 55,p. 1329 - 1345.

17
[ 39903-01-0 ]
methyl 3-(6-amino-5-[3-(4-piperidinyl)propanoyl]oxy}-3-pyridyl)propanoate [ No CAS ]

References: [1]Heterocycles,2001,vol. 55,p. 1329 - 1345.

18
[ 39903-01-0 ]
methyl (E)-3-{2-[(1-benzyl-4-piperidinyl)methyl]oxazolo[4,5-b]pyridin-6-yl}-2-propenoate [ No CAS ]

References: [1]Heterocycles,2001,vol. 55,p. 1329 - 1345.

19
[ 39903-01-0 ]
[ 364385-56-8 ]

References: [1]Heterocycles,2001,vol. 55,p. 1329 - 1345.

20
[ 39903-01-0 ]
[ 364385-49-9 ]

References: [1]Heterocycles,2001,vol. 55,p. 1329 - 1345.

21
[ 39903-01-0 ]
[ 364385-42-2 ]

References: [1]Heterocycles,2001,vol. 55,p. 1329 - 1345.

22
[ 39903-01-0 ]
[ 364385-41-1 ]

References: [1]Heterocycles,2001,vol. 55,p. 1329 - 1345.

23
[ 39903-01-0 ]
[ 364385-50-2 ]

References: [1]Heterocycles,2001,vol. 55,p. 1329 - 1345.

24
[ 39903-01-0 ]
[ 364385-57-9 ]

References: [1]Heterocycles,2001,vol. 55,p. 1329 - 1345.

25
[ 39903-01-0 ]
methyl 3-[2-(4-piperidinylmethyl)oxazolo[4,5-b]pyridin-6-yl]propanoate, formate salt [ No CAS ]

References: [1]Heterocycles,2001,vol. 55,p. 1329 - 1345.

26
[ 39903-01-0 ]
[ 364385-37-5 ]

References: [1]Heterocycles,2001,vol. 55,p. 1329 - 1345.

27
[ 39903-01-0 ]
methyl 3-{2-[2-(4-piperidinyl)ethyl]oxazolo[4,5-b]pyridin-6-yl}propanoate, formate salt [ No CAS ]

References: [1]Heterocycles,2001,vol. 55,p. 1329 - 1345.

28
[ 39903-01-0 ]
methyl 3-{2-[4-([amino(imino)methyl]amino}methyl)phenyl]oxazolo[4,5-b]pyridin-6-yl}propanoate hydrochloride [ No CAS ]

References: [1]Heterocycles,2001,vol. 55,p. 1329 - 1345.

29
[ 39903-01-0 ]
methyl 3-{2-[4-([amino(imino)methyl]amino}methyl)phenyl]oxazolo[4,5-b]pyridin-6-yl}propanoate, nitrate salt [ No CAS ]

References: [1]Heterocycles,2001,vol. 55,p. 1329 - 1345.

30
[ 39903-01-0 ]
6-vinyl-2-phenyloxazolo<4,5-b>pyridine [ No CAS ]

References: [1]Heterocycles,1995,vol. 41,p. 2799 - 2810.

31
[ 39903-01-0 ]
[ 174469-37-5 ]

References: [1]Heterocycles,1995,vol. 41,p. 2799 - 2810.

32
[ 39903-01-0 ]
6-cyano-2-phenyloxazolo<4,5-b>pyridine [ No CAS ]

References: [1]Heterocycles,1995,vol. 41,p. 2799 - 2810.

33
[ 39903-01-0 ]
6-butyl-2-phenyloxazolo<4,5-b>pyridine [ No CAS ]

References: [1]Heterocycles,1995,vol. 41,p. 2799 - 2810.

34
[ 39903-01-0 ]
(2-phenyloxazolo<4,5-b>pyridin-6-yl)ethanone [ No CAS ]

References: [1]Heterocycles,1995,vol. 41,p. 2799 - 2810.

35
[ 39903-01-0 ]
[ 174469-39-7 ]

References: [1]Heterocycles,1995,vol. 41,p. 2799 - 2810.

36
[ 39903-01-0 ]
[ 174469-38-6 ]

References: [1]Heterocycles,1995,vol. 41,p. 2799 - 2810.

37
[ 39903-01-0 ]
6-phenyl-2-phenyloxazolo<4,5-b>pyridine [ No CAS ]

References: [1]Heterocycles,1995,vol. 41,p. 2799 - 2810.

38
[ 39903-01-0 ]
[ 174469-34-2 ]

References: [1]Heterocycles,1995,vol. 41,p. 2799 - 2810.

39
[ 39903-01-0 ]
(2-phenyloxazolo<4,5-b>pyridin-6-yl)phenone [ No CAS ]

References: [1]Heterocycles,1995,vol. 41,p. 2799 - 2810.

40
[ 39903-01-0 ]
[ 174469-35-3 ]

References: [1]Heterocycles,1995,vol. 41,p. 2799 - 2810.

41
[ 877400-08-3 ]
[ 39903-01-0 ]
[ 877400-10-7 ]

Yield	Reaction Conditions	Operation in experiment
41%	With caesium carbonate; In N,N-dimethyl-formamide; at 60℃; for 17h;	To a stirred solution of 28-6 (1.15 g, 3.78 mmol) and <strong>[39903-01-0]2-amino-5-bromo-pyridin-3-ol</strong> (3.78 g, 3.78 mmol) in DMF (8 mL, 0.5 M) was added CS2CO3 (1.23 g, 3.78 mmol). The reaction mixture was stirred for 17 hours at 60 °C. The reaction was cooled to room temperature and water (20 mL) was added. The solution was extracted with EtOAc (4 x 20 mL), dried with Na2SO4 and removal of the solvent in vacuo. The crude reaction was purified by silica gel column chromatography to afford a light yellow solid 28-7 (600 mg, 41percent yield). 1H NMR (CDCI3, 400 MHz) 87.69 (s, 1H), 7.04 (t, 7.04), 6.01 (m, 1H), 4.80 (bs, 2H), 1.82(d, 3H).

References: [1]Patent: WO2006/21881,2006,A2 .Location in patent: Page/Page column 85; 86.

42
[ 859204-45-8 ]
[ 39903-01-0 ]
t-butyl 2-(6-amino-3-bromo-5-hydroxy-2-pyridylazo)-5-phenyl-3-thenoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sulfuric acid; sodium nitrite; In pyridine; water;	D. t-Butyl 2-(6-amino-3-bromo-5-hydroxy-2-pyridylazo)-5-phenyl-3-thenoate A solution of t-butyl 2-amino-5-phenyl-3-thenoate (8.26 g; 0.03 mole) in 2:5 acid (120 ml) (see Example 1) was chilled to -2° C. and concentrated sulfuric acid (5 ml) was added at such a rate that the temperature did not exceed 2° C.; a solution of sodium nitrite (2.16 g) in water (5 ml) was added dropwise below 2° C. The resulting diazonium solution was stirred at -2° C. to +2° C. for 45 minutes, then added in a slow stream with magnetic stirring to a cold (below 5° C.) solution of <strong>[39903-01-0]2-amino-5-bromo-3-pyridinol</strong> (Example 2-L) (5.67 g; 0.03 mole) in pyridine (30 ml) and 2:5 acid (90 ml). The dye solution was stirred at 0° to 5° C. for 1.5 hours, then the cooling bath was removed and the mixture stirred for an additional 30 minutes. After drowning in cold water (2.5 liters), the dye was collected on a filter, washed with water and dried to yield 14.7 g of material with only traces of impurities.

References: [1]Patent: US4385104,1983,A .

43
[ 16867-03-1 ]
[ 39903-01-0 ]

Yield	Reaction Conditions	Operation in experiment
	With bromine; In ethanol;	B. The 2-amino-5-bromo-3-pyridinol is prepared by dissolving 110.0 g of 2-amino-3-pyridinol in 250 ml of 95percent ethanol. The solution is cooled to about 5° C. and at that temperature is treated with 160 g of liquid bromine during 2 hours. The mixture is stirred for 1 hour after the addition is completed and then concentrated to give 170.6 g of 2-amino-5-bromo-3-pyridinol.

References: [1]Archiv der Pharmazie,2011,vol. 344,p. 158 - 164.
[2]Journal of Medicinal Chemistry,2014,vol. 57,p. 828 - 835.
[3]Tetrahedron Letters,2014,vol. 55,p. 1528 - 1531.
[4]Patent: WO2016/97918,2016,A1 .
[5]Patent: US4022897,1977,A .

44
[ 35486-42-1 ]
[ 12775-96-1 ]
[ 39903-01-0 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium hydroxide; In tetrahydrofuran; water; ethyl acetate;	EXAMPLE 4 A mixture of 6.5 parts of 2-amino-3,5-dibromopyridine, 12 parts of potassium hydroxide (85percent), 0.5 part of copper powder and 100 parts of water is stirred under nitrogen in an autoclave for 10 hours at 170° C. The dark-coloured solution is neutralised with concentrated hydrochloric acid, saturated with sodium chloride and extracted three times in the warm state with an ethyl acetate/tetrahydrofuran mixture (9:1). The combined organic extracts are filtered through Hyflo, dried with sodium sulphate and filtered. After the solvent has been evaporated off, the residue is taken up in a small amount of hot ethyl acetate and chromatographed through silica gel. After removal of the ethyl acetate, there are obtained 2.2 parts (46.3percent of theory) of 2-amino-3-hydroxy-5-bromopyridine, m.p. 205°-208° C.

References: [1]Patent: US4033975,1977,A .

45
[ 12775-96-1 ]
[ 38185-55-6 ]
[ 39903-01-0 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium hydroxide; In tetrahydrofuran; diethylene glycol dimethyl ether; cyclohexane; ethylene glycol; ethyl acetate;	EXAMPLE 5 A mixture of 5 parts of 2-amino-3-chloro-5-bromopyridine, 20 parts of potassium hydroxide (85percent), 3 parts of diethylene glycol dimethyl ether, 0.3 part of copper-bronze and 40 parts of glycol is stirred under nitrogen for 7 hours at 170°-175° C. After cooling, the dark-coloured solution is neutralised with concentrated hydrochloric acid, saturated with sodium chloride and extracted twice in the warm state with ethyl acetate/tetrahydrofuran (9:1). The organic layer is extracted by shaking with a saturated sodium chloride solution; the ethyl acetate phase is then filtered through Hyflo, dried with magnesium sulphate and purified with active charcoal. The clear yellow solution is concentrated almost to dryness and chromatographed through a short silica-gel column with ethyl acetate/cyclohexane (2:1). The yield is 2 parts of 2-amino-3-hydroxy-5-bromopyridine, m.p. 204°-207° C. (44.1percent of theory).

References: [1]Patent: US4033975,1977,A .

46
[ 6959-47-3 ]
[ 39903-01-0 ]
[ 941603-82-3 ]

Yield	Reaction Conditions	Operation in experiment
27%	With potassium carbonate; sodium iodide; In acetone;Heating / reflux;	5-Bromo-3-(pyridine-2-ylmethoxy)-pyridin-2-ylamine To a suspension of <strong>[39903-01-0]2-amino-5-bromo-pyridin-3-ol</strong> (2.00 g, 10 mmol) in acetone (80 mL) was added to 2-chloromethyl-pyridine hydrochloride (2.24 g, 13.7 mmol), K2CO3 (4.38 g, 31.7 mmol) and NaI (4.74 g, 31.7 mmol). The mixture was heated to reflux overnight. After cooling, the mixture was diluted with water and then extracted with EtOAc (3x). The combined organics were washed with brine, dried (Na2SO4) and concentrated. Purification by column chromatography (silica gel, hexanes/EtOAc, 1 :4) gave the title compound (830 mg, 27percent) as a brown oil: 1H NMR (300 MHz, delta 8.61-8.57 (m, IH), 7.88-7.84 (m, IH), 7.66 (d, J = 8.1 Hz, IH), 7.60 (d, J= 1.8 Hz, IH), 7.35 (dd, J= 7.5, 3.0 Hz, IH), 7.28 (d, J= 2.1 Hz, IH) <n="94"/>6.06 (s, 2H), 5.21 (s, 2H); ESI MS m/z 280 (M + H)+.

References: [1]Patent: WO2007/67416,2007,A2 .Location in patent: Page/Page column 56; 92-93.

47
[ 6959-48-4 ]
[ 39903-01-0 ]
[ 941603-84-5 ]

Yield	Reaction Conditions	Operation in experiment
29%	With potassium carbonate; sodium iodide; In acetone;Heating / reflux;	00 suspension of <strong>[39903-01-0]2-amino-5-bromo-pyridin-3-ol</strong> (1.00 g, 5.29 mmol) in acetone (40 mL) was added to a solution of 3-chloromethylpyridine hydrochloride (1.12 g, 6.87 mmol), K2CO3 (2.19 g, 15.8 mmol) and NaI (2.37 g, 15.8 mmol). The mixture was heated to reflux overnight. After cooling, the mixture was dissolved in water and extracted with EtOAc (3x). The combined organics were washed with brine, dried and concentrated. Purification by column chromatography (silica gel, hexanes/EtOAc, 1 :4) gave the title compound (430 mg, 29percent) as a brown oil: 1H NMR (300 MHz, DMSO-^) delta 8.71 (d, J= 1.8 Hz, IH), 8.55 (d, J= 3.0 Hz IH), 7.96-7.92 (m, IH), 7.60 (d, J= 3.0 Hz, IH), 7.45-7.35 (m, IH), 7.34 (d, J= 3.0 Hz, IH), 6.04 (br s, 2H), 5.20 (s, 2H); ESI MS m/z 280 (M + H)+.

References: [1]Patent: WO2007/67416,2007,A2 .Location in patent: Page/Page column 57; 94.

48
[ 108-24-7 ]
[ 39903-01-0 ]
[ 941603-86-7 ]

Yield	Reaction Conditions	Operation in experiment
	In 1,4-dioxane; for 20h;Heating / reflux;	To a solution of <strong>[39903-01-0]2-amino-5-bromopyridin-3-ol</strong> (1.89 g, 10.0 mmol) in 1,4-dioxane (20 mL) was added acetic anhydride (4.7 mL, 50 mmol) and the mixture was heated to reflux for 20 h. After cooling, the solvent was removed in vacuo. Purification by column chromatography <n="97"/>(silica gel, hexanes/EtOAc, 70:30 to 50:50) gave the title compound (2.30 g, 73percent) as a white solid: 1H NMR (300 MHz, CDCl3) delta 8.52 (d, J= 2.1 Hz, IH), 7.87 (d, J= 2.1 Hz, IH), 2.30 (s, 6H), 2.29 (s, 3H); ESI MS m/e 315 (M + H)+.

References: [1]Patent: WO2007/67416,2007,A2 .Location in patent: Page/Page column 57; 95-96.

49
[ 59154-46-0 ]
[ 39903-01-0 ]
[ 894852-01-8 ]

Yield	Reaction Conditions	Operation in experiment
84%	With potassium carbonate; In acetone; for 18h;Heating / reflux;	a) 7-Bromo-2,2-dimethyl-4H-pyrido[3,2-] [ 1 ,4]oxazin-3 -one; To a mixture of 2-amino-5-bromopyridin-3-ol (0.500 g, 2.64 mmol) and K2CO3 (1.09 g, 7.93 mmol) in acetone (11.0 niL) was added ethyl bromoisobutyrate (0.50 mL, 3.4 mmol). The solution was stirred under N2 for 18 h and then heated to reflux. After 18 h, the solution was cooled and concentrated. The light-pink, sweet-smelling solid was dissolved in CH2Cl2 (50 mL) and MeOH (5 mL). The solution was diluted with H2O (150 mL) and then washed with CH2Cl2 (3 x 75 mL). The combined organic layers were washed with brine (2 x 100 mL), dried (Na2SO4) and concentrated to yield the title compound (0.57 g, 84percent) as an off-white solid: 1H NMR (300 MHz, DMSO-J,*) delta 11.39 (s, IH), 8.03 (d, J=1.2 Hz, IH), 7.66 (d, 0.9 Hz, IH), 1.43 (s, 6H).

References: [1]Patent: WO2007/53131,2007,A2 .Location in patent: Page/Page column 130.

Yield	Reaction Conditions	Operation in experiment
84%		Synthesis Example 7 Synthesis of Exemplified Compound No. 32 2-amino-5-bromopyridin-3-ol [19] was synthesised by the method described in Heterocycles, 55, 1329 (2001). Then, 6-bromo-2-phenyl-oxazolo[4,5-b]pyridine [21] (pale yellow crystal) was obtained from [19] and benzoic acid [20] in 84percent yield. The following compounds were placed in a 300-ml three-necked flask, and the mixture was stirred under nitrogen atmosphere at room temperature. During the stirring, an aqueous solution of 3 g of sodium carbonate in 30 ml of water was added dropwise to the mixture. 1.95 g (7.09 mmol) of 2-amino-5-bromopyridine-3-ol [19] 1.50 g (3.36 mmol) of a 9,9-dimethylfluorene-2,7-diboronic acid pinacol ester [4] 75 ml of toluene and 38 ml of ethanol Next, 0.39 g (0.34 mmol) of tetrakis(triphenylphosphine)palladium(0) was added to the mixture. After the mixture was stirred at room temperature for 10 minutes, the temperature of the mixture was increased to 78° C., and the mixture was stirred under heating and reflux for 4 hours. The reaction liquid was filtrated, and the resultant crude product was dissolved in 300 ml of chloroform at 70° C. The solution was purified with a silica gel column (toluene/acetic ether 5/1), whereby 1.53 g of Exemplified Compound No. 32 (white crystal) was obtained (78percent yield).

51
[ 107-20-0 ]
[ 39903-01-0 ]
[ 1379358-48-1 ]

Yield	Reaction Conditions	Operation in experiment
92%	In ethanol; water; at 60℃;	[00188] 2-Amino-3-hydroxy-5-bromopyridine (Heterocycles, 1995, 41, 2799) (124 mg, 0.65 mmol) was dissolved in EtOH (3 niL) and added chloroacetaldehyde (0.2 niL, 1.3 mmol, 50percent in water) and the resulting solution heated at 60 °C overnight. The solvents were then removed and the solids were crystallized from acetone to give 6-bromoimidazo[l,2-a]pyridin-8-ol hydrochloride (151 mg, 92percent).
92%	In ethanol; water; at 60℃;	2-Amino-3-hydroxy-5-bromopyridine (Heterocycles, 41 :2799 (1995)) (124 mg, 0.65 mmol) was dissolved in EtOH (3 niL) and added chloroacetaldehyde (0.2 mL, 1.3 mmol, 50percent in water) and the resulting solution heated at 60 0C overnight. The solvents were then removed and the solids were crystallized from acetone to give 6-bromoimidazo[l,2-a]pyridin-8-ol hydrochloride (151 mg, 92percent)

References: [1]Patent: WO2009/155389,2009,A1 .Location in patent: Page/Page column 88-89.
[2]Patent: WO2009/155388,2009,A1 .Location in patent: Page/Page column 98-99.

52
[ 39903-01-0 ]
[ 75-03-6 ]
5-bromo-3-ethoxypyridin-2-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
59%	With sodium hydroxide; In dichloromethane; water; at 20℃; for 16h;	To a stirred solution of <strong>[39903-01-0]2-amino-5-bromopyridine-3-ol</strong> (25 g, 132.9 mmol) in dichloromethane (150 niL) was added iodoethane (41.43 g, 265 mmol), aliquat (7.5 g) and 40percent aqueous sodium hydroxide (150 mL) at RT, followed by stirring for 16 h. The reaction mixture was diluted with water (150 mL) and extracted with dichloromethane (2 x 300 mL). The combined organic layers were concentrated to dryness in vacuo and the resulting residue was purified by column chromatography (silica gel, 100-200 mesh, 20percent ethyl acetate in hexane) affording 5-bromo-3-ethoxypyridin-2-amine as and off white solid (17 g, 59percent): NMR (300 MHz, DMSO-d6) delta 7.58 (s, 1H), 7.18 (s, 1H), 5.85 (s, 2H), 4.2 - 3.8 (m, 2H), 1.20 - 1.40 (m, 1H), 0.65 - 0.55 (m, 2H).
59%	With sodium hydroxide; In dichloromethane; water; at 20℃; for 16h;	Preparative Example 2 Step 1: 5-bromo-3-ethoxypyridin-2-amine To a stirred solution of <strong>[39903-01-0]2-amino-5-bromopyridine-3-ol</strong> (25 g, 132.9 mmol) in dichloromethane (150 niL) was added iodoethane (41.43 g, 265 mmol), aliquat (7.5 g) and 40percent aqueous sodium hydroxide (150 niL) at RT, followed by stirring for 16 h. The reaction mixture was diluted with water (150 mL) and extracted with dichloromethane (2 x 300 mL). The combined organic layers were concentrated to dryness in vacuo and the resulting residue was purified by column chromatography (silica gel, 100- 200 mesh, 20percent ethyl acetate in hexane) affording 5-bromo-3-ethoxypyridin-2-amine as and off white solid (17 g, 59percent): lU NMR (300 MHz, DMSO-d6) delta 7.58 (s, 1H), 7.18 (s, 1H), 5.85 (s, 2H), 4.2 - 3.8 (m, 2H), 1.20 - 1.40 (m, 1H), 0.65 - 0.55 (m, 2H).
46%	With sodium hydroxide; In dichloromethane; water; at 20℃; for 21h;	00105] As shown in step 4-iv of Scheme 20, Compound 1013 (19.0 g, 100.5 mmol) was dissolved in DCM (90 mL), and iodoethane (9.0 mL, 110.6 mmol), Adogen.(R). 464 (methyltrialkyl(C8-Cio)ammonium chloride, 0.6 g), and 40percent NaOH(aq) (90 mL) were added. The reaction was stirred at RT for 21 h. The DCM layer was separated, and the aqueous layer was diluted with water (100 mL) and extracted with DCM (2 x 100 mL). The combined organic extracts were dried over Na2SO4 and concentrated under reduced pressure. The crude product was purified on a silica plug eluting with 40percent ethyl acetate/hexanes to afford 2- amino-5-bromo-3-ethoxypyridine (Compound 1014, 10.0 g, 46percent yield) as a white solid: ESMS (M+H) 217, 219. 1H NMR (DMSO-d6) delta 7.6 (s, IH), 7.1 (s, IH), 5.8 (br, 2H), 4.0 (q, 2H), 1.3 (t, 3H).

46%

With sodium hydroxide; In dichloromethane; water; at 20℃; for 21h;

As shown in step 4-iv of Scheme 20, Compound 1013 (19.0 g, 100.5 mmol) was dissolved in DCM (90 mL), and iodoethane (9.0 mL, 110.6 mmol), Adogen.(R). 464 (methyltrialkyl(C8-Cio)ammonium chloride, 0.6 g), and 40percent NaOH(aq) (90 mL) were added. The reaction was stirred at RT for 21 h. The DCM layer was separated, and the aqueous layer was diluted with water (100 mL) and extracted with DCM (2 x 100 mL). The combined organic extracts were dried over Na2SO4 and concentrated under reduced pressure. The crude product was purified on a silica plug eluting with 40percent ethyl acetate/hexanes to afford 2- amino-5-bromo-3-ethoxypyridine (Compound 1014, 10.0 g, 46percent yield) as a white solid: ESMS (M+H) 217, 219. 1H NMR (DMSO-d6) delta 7.6 (s, IH), 7.1 (s, IH), 5.8 (br, 2H), 4.0 (q, 2H), 1.3 (t, 3H).

References: [1]Patent: WO2014/111496,2014,A1 .Location in patent: Page/Page column 95.
[2]Patent: WO2016/142310,2016,A1 .Location in patent: Page/Page column 60.
[3]Patent: WO2010/96389,2010,A1 .Location in patent: Page/Page column 43; 44.
[4]Patent: WO2010/135014,2010,A1 .Location in patent: Page/Page column 50-51.

53
[ 39903-01-0 ]
[ 122-51-0 ]
[ 1260863-86-2 ]

Yield	Reaction Conditions	Operation in experiment
60%	With toluene-4-sulfonic acid; for 5h;Reflux;	Preparation 56-Bromo-oxazolo[4,5-b]pyridine[00122] 2-Amino-5-bromo-3-hydroxypyridine (200 mg, 1.06 mmol) is dissolved in 3 ml of triethylortoformate and a catalytic amount of p-toluenesulfonic acid is added. The mixture is heated to reflux for 5 h, then cooled, diluted with DCM and washed with saturated sodium bicarbonate solution. The organic phase is dried over anhydrous sodium sulfate and evaporated to dryness. The residue is purified by flash column chromatography to afford 212 mg (60percent) of the title compound.

References: [1]Patent: WO2011/15343,2011,A1 .Location in patent: Page/Page column 40.

54
[ 57267-03-5 ]
[ 39903-01-0 ]
[ 1264193-15-8 ]

Yield	Reaction Conditions	Operation in experiment
	With toluene-4-sulfonic acid; In 1,4-dioxane; for 5h;Reflux;	Preparation 10.6-Bromo-oxazolo[4,5-b]pyridine-2-carboxylic acid [00132] 2-Amino-5-bromo-3-hydroxypyridine (200 mg, 1.06 mmol) is dissolved in 3 mL of dioxane, triethoxyacetic acid ethyl ester (0.5 mL) and a catalytic amount of p- toluenesulfonic acid are added. The mixture is heated to reflux for 5 h, then cooled, diluted with DCM and washed with saturated sodium bicarbonate solution. The organic phase is dried over anhydrous sodium sulfate and evaporated to dryness. The residue is purified by flash column chromatography to afford 6-bromo-oxazolo[4,5-b]pyridine-2- carboxylic acid ethyl ester which is dissolved in a mixture of THF (2 mL) and water (0.5 mL). Lithium hydroxide (25 mg, 1 mmol) is added and the mixture is stirred at r.t. for 15 min., then neutralized with diluted hydrochloric acid until pH 7 is reached. The mixture is extracted with EtOAc, the organic phase is dried over anhydrous sodium sulfate and evaporated to dryness to afford sufficiently pure title compound.

References: [1]Patent: WO2011/15343,2011,A1 .Location in patent: Page/Page column 42-43.

55
[ 39903-01-0 ]
[ 1264193-14-7 ]

References: [1]Patent: WO2011/15343,2011,A1 .

Historical Records

Technical Information

• Alkyl Halide Occurrence • Appel Reaction • Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions • Chan-Lam Coupling Reaction • Chugaev Reaction • Corey-Kim Oxidation • Dess-Martin Oxidation • General Reactivity • Grignard Reaction • Hiyama Cross-Coupling Reaction • Hydride Reductions • Jones Oxidation • Kinetics of Alkyl Halides • Kumada Cross-Coupling Reaction • Leuckart-Wallach Reaction • Mannich Reaction • Martin's Sulfurane Dehydrating Reagent • Mitsunobu Reaction • Moffatt Oxidation • Oxidation of Alcohols by DMSO • Petasis Reaction • Preparation of Alcohols • Preparation of Amines • Reactions of Alcohols • Reactions of Alkyl Halides with Reducing Metals • Reactions of Amines • Reactions of Dihalides • Reactions with Organometallic Reagents • Ritter Reaction • Sharpless Olefin Synthesis • Specialized Acylation Reagents-Vilsmeier Reagent • Stille Coupling • Substitution and Elimination Reactions of Alkyl Halides • Suzuki Coupling • Swern Oxidation • Ugi Reaction

Pharmaceutical Intermediates of
[ 39903-01-0 ]

Crizotinib Related Intermediates

[877397-70-1]

(R)-3-(1-(2,6-Dichloro-3-fluorophenyl)ethoxy)-2-nitropyridine

[877399-51-4]

(R)-tert-Butyl 4-(4-(6-amino-5-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)pyridin-3-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

[1207175-73-2]

tert-Butyl (5-bromo-3-hydroxypyridin-2-yl)carbamate

[756520-66-8]

1-(2,6-Dichloro-3-fluorophenyl)ethanol

[877399-00-3]

(R)-5-Bromo-3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)pyridin-2-amine

Related Functional Groups of
[ 39903-01-0 ]

Bromides

A240596 [42409-58-5]

5-Bromo-3-methoxypyridin-2-amine

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A232237 [947249-13-0]

5-Bromo-3-(difluoromethoxy)pyridin-2-amine

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A195862 [34950-82-8]

7-Bromo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine

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3-(Benzyloxy)-5-bromopyridin-2-amine

Similarity: 0.76

Alcohols

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2-Amino-6-bromopyridin-3-ol

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A104964 [20348-16-7]

2-Amino-6-methylpyridin-3-ol

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A152721 [34206-49-0]

5-Bromopyridine-2,3-diol

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A275854 [857429-79-9]

2,5-Dibromopyridin-3-ol

Similarity: 0.73

A107140 [91420-25-6]

5-Bromo-2-methylpyridin-3-ol

Similarity: 0.72

Amines

A240596 [42409-58-5]

5-Bromo-3-methoxypyridin-2-amine

Similarity: 0.92

A232237 [947249-13-0]

5-Bromo-3-(difluoromethoxy)pyridin-2-amine

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5-Bromo-3-methoxy-6-methylpyridin-2-amine

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A249349 [754230-78-9]

3-(Benzyloxy)-5-bromopyridin-2-amine

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A174045 [934758-27-7]

2-Amino-6-bromopyridin-3-ol

Similarity: 0.74

Related Parent Nucleus of
[ 39903-01-0 ]

Pyridines

A240596 [42409-58-5]

5-Bromo-3-methoxypyridin-2-amine

Similarity: 0.92

A232237 [947249-13-0]

5-Bromo-3-(difluoromethoxy)pyridin-2-amine

Similarity: 0.81

A265426 [947249-16-3]

5-Bromo-3-methoxy-6-methylpyridin-2-amine

Similarity: 0.81

A249349 [754230-78-9]

3-(Benzyloxy)-5-bromopyridin-2-amine

Similarity: 0.76

A174045 [934758-27-7]

2-Amino-6-bromopyridin-3-ol

Similarity: 0.74

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P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

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

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CAS No.: 39903-01-0

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CAS No.: 39903-01-0

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[ 39903-01-0 ] Synthesis Path-Downstream 1~55

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[ 39903-01-0 ]

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{[proInfo.proName]}

CAS No.: 39903-01-0

{[proInfo.proName]}

CAS No.: 39903-01-0

Alternative Products

Product Details of [ 39903-01-0 ]

Safety of [ 39903-01-0 ]

Computational Chemistry of [ 39903-01-0 ] Show Less

Physicochemical Properties

Lipophilicity

Water Solubility

Pharmacokinetics

Druglikeness

Medicinal Chemistry

Application In Synthesis of [ 39903-01-0 ]

[ 39903-01-0 ] Synthesis Path-Downstream 1~55

Related Products

Historical Records

Technical Information

Categories

Pharmaceutical Intermediates of [ 39903-01-0 ]

Crizotinib Related Intermediates

Related Functional Groups of [ 39903-01-0 ]

Bromides

Alcohols

Amines

Related Parent Nucleus of [ 39903-01-0 ]

Pyridines

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Molarity Calculator

Total Compounds Calculator

Dissolution Calculator

Pharmaceutical Intermediates of
[ 39903-01-0 ]

Related Functional Groups of
[ 39903-01-0 ]

Related Parent Nucleus of
[ 39903-01-0 ]