[ CAS No. 53472-18-7 ] {[proInfo.proName]}

Name: 53472-18-7|5-Bromoquinolin-8-amine|97%
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Quality Control of [ 53472-18-7 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 53472-18-7 ]

Product Details of [ 53472-18-7 ]

CAS No. :	53472-18-7	MDL No. :	MFCD01571832
Formula :	C₉H₇BrN₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	GEABITRRZOHARP-UHFFFAOYSA-N
M.W :	223.07	Pubchem ID :	613829
Synonyms :

Calculated chemistry of [ 53472-18-7 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	10
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	1.0
Num. H-bond donors :	1.0
Molar Refractivity :	53.85
TPSA :	38.91 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	Yes
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.99 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.78
Log Po/w (XLOGP3) :	0.94
Log Po/w (WLOGP) :	2.59
Log Po/w (MLOGP) :	1.9
Log Po/w (SILICOS-IT) :	2.4
Consensus Log Po/w :	1.92

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.43
Solubility :	0.825 mg/ml ; 0.0037 mol/l
Class :	Soluble
Log S (Ali) :	-1.34
Solubility :	10.1 mg/ml ; 0.0453 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-4.2
Solubility :	0.014 mg/ml ; 0.000063 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.64

Safety of [ 53472-18-7 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 53472-18-7 ]

* 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.

Upstream synthesis route of [ 53472-18-7 ]
Downstream synthetic route of [ 53472-18-7 ]

[ 53472-18-7 ] Synthesis Path-Upstream 1~5

1
[ 578-66-5 ]
[ 53472-18-7 ]

Yield	Reaction Conditions	Operation in experiment
51%	With N-Bromosuccinimide In acetonitrile at 25℃; for 1.25 h;	4.1.16 5-Bromo-8-aminoquinoline (21) To solution of compound 12 (1.0 g, 6.94 mmol) in 46.0 mL of acetonitrile, a portion of NBS (605 mg, 3.40 mmol) was added. The reaction mixture was stirred at 25 °C for 15 min, then a second portion of NBS (667 mg, 3.75 mmol) was added. The reaction was stirred for 1 h at 25 °C. The solvent was evaporated under reduced pressure and the residue taken up with EtOAc and washed with water (3 * 50 mL). The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified by flash chromatography on silica gel (10percent EtOAc in petroleum ether) to afford the title compound as an amorphous yellow solid (51percent yield). ¹H NMR (300 MHz, CDCl₃) δ 8.76 (d, 1H, J = 6.0 Hz), 8.43 (d, 1H, J = 9.0 Hz), 7.56 (d, 1H, J = 12.0), 7.48 (q, 1H, J = 3.0 Hz), 6.80 (d, 1H, J = 6.0 Hz); ESI-MS m/z 222.9 [M+H]⁺.
50%	With N-Bromosuccinimide In acetone at 20℃; for 0.5 h;	Quinolin-8-amine (0.20 g, 1.38 μMol) was dissolved in acetonitrile (20 mL), and N-bromosuccinimide (0.26 g,1.43 μMol) was added to the solution. The mixture was stirred at room temperature for 30 minutes. Water was addedto the mixture. The organic layer was extracted with ethyl acetate, dried over anhydrous sodium sulfate, and concentratedunder reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate = 90/10-> 70/30) to obtain compound 117-1 (0.15 g, 50percent).1H NMR (300 MHz, DMSO-d6, δ): 8.76 (d, J = 3.3 Hz, 1H), 8.42 (d, J = 8.1 Hz, 1H), 7.56 (d, J = 8.4 Hz, 1H), 7.48 (dd,J = 8.4, 4.2 Hz, 1H), 6.80 (d, J = 8.1 Hz, 1H), 5.04 (br, 2H).
760 mg	With N-Bromosuccinimide In acetonitrile at 20℃; for 2 h;	To a solution of 8-aminoquinoline (1 g, 4.8 mmol) in CH3CN (30 mL) were added NBS (1.28 g, 7.2 mmol). The reaction mixture was stirred at RT for 2 hour. The residue was treated with water and extracted with EA. The extracts were concentrated and the residue purifiled by silica gel chromatography to afford 5-bromo-8-quinolylamine (760 mg).

Reference： [1] European Journal of Medicinal Chemistry, 2019, p. 290 - 320
[2] Patent: EP3401309, 2018, A1, . Location in patent: Paragraph 0859
[3] Patent: WO2010/30722, 2010, A1, . Location in patent: Page/Page column 46
[4] Patent: WO2016/77240, 2016, A2, . Location in patent: Page/Page column 90; 104

2
[ 578-66-5 ]
[ 53472-18-7 ]
[ 36107-02-5 ]

Reference： [1] Chemical Science, 2018, vol. 9, # 7, p. 1782 - 1788
[2] Letters in Drug Design and Discovery, 2017, vol. 14, # 12, p. 1415 - 1424

3
[ 176967-80-9 ]
[ 53472-18-7 ]

Reference： [1] Journal fuer Praktische Chemie (Leipzig), 1889, vol. <2> 40, p. 386[2] Journal fuer Praktische Chemie (Leipzig), 1893, vol. <2> 48, p. 269

4
[ 53472-18-7 ]
[ 504-63-2 ]
[ 40000-20-2 ]

Reference： [1] Patent: CN108530443, 2018, A, . Location in patent: Paragraph 0058; 0060-0062

5
[ 53472-18-7 ]
[ 56-81-5 ]
[ 40000-20-2 ]

Reference： [1] Journal of the Chemical Society, 1946, p. 155

[ 53472-18-7 ] Synthesis Path-Downstream 1~72

1
[ 53472-18-7 ]
[ 56-81-5 ]
[ 40000-20-2 ]

Reference： [1]Journal of the Chemical Society,1946,p. 155

2
[ 176967-80-9 ]
[ 53472-18-7 ]

Reference： [1]Journal fur praktische Chemie (Leipzig 1954),1889,vol. <2> 40,p. 386
Journal fuer Praktische Chemie (Leipzig),1893,vol. <2> 48,p. 269

4
5-bromo-8-acetylamino-quinoline [ No CAS ]
[ 53472-18-7 ]

Reference： [1]Journal fur praktische Chemie (Leipzig 1954),1896,vol. <2> 53,p. 392

5
[ 53472-18-7 ]
[ 292638-85-8 ]
3-(5-bromo-quinolin-8-ylamino)-propionic acid methyl ester [ No CAS ]

Reference： [1]Chemistry of Heterocyclic Compounds,2000,vol. 36,p. 432 - 438

6
[ 53472-18-7 ]
[ 79-10-7 ]
3-(5-bromo-quinolin-8-ylamino)-propionic acid [ No CAS ]

Reference： [1]Chemistry of Heterocyclic Compounds,2000,vol. 36,p. 432 - 438

7
[ 53472-18-7 ]
[ 97-65-4 ]
1-(5-bromo-quinolin-8-yl)-5-oxo-pyrrolidine-3-carboxylic acid [ No CAS ]

Reference： [1]Chemistry of Heterocyclic Compounds,2000,vol. 36,p. 818 - 821

8
[ 53472-18-7 ]
5-phenoxy-[1,10]phenanthroline [ No CAS ]

Reference： [1]Journal of the Chemical Society,1946,p. 155

9
[ 53472-18-7 ]
[ 189306-94-3 ]
[ 720716-44-9 ]

Yield	Reaction Conditions	Operation in experiment
25%	In ethanol; at 20 - 50℃; for 216h;	To a stirred solution of 40 mg (0.139 MMOL) of 5-acetyl-2-ethyl-4-nitro-6- phenylpyridazin-3 (2H)-one (Dal Piaz, V ET AL, J. Med. Chem. 1997,40, 1417) in ethanol (4 mL), <strong>[53472-18-7]8-amino-5-bromoquinoline</strong> (47 mg, 0.209 MMOL) was added. The resulting mixture was stirred at room temperature for five days and heated at 50 C during four days. The solvent was evaporated and the residue purified by column chromatography (silica gel, hexane/ethyl acetate 4: 1) to yield the title compound (16, mg, 25% YIELD)

Reference： [1]Patent: WO2004/58729,2004,A1 .Location in patent: Page 38; 134

10
[ 578-66-5 ]
[ 53472-18-7 ]

Yield	Reaction Conditions	Operation in experiment
56%	With tetrabutylammomium bromide; copper(ll) bromide; In ethanol; at 25℃;	General procedure: A round bottom flask was charged with Bu4NBr (2 mmol, 0.64 g), EtOH (8 mL) and 2-methylaniline (2 mmol, 0.21 g) followed by CuBr2 (3 mmol, 0.67 g). The resulted mixture was stirred at 25 C. After the completion of the reaction (monitored by TLC), the solvent was evaporated under reduced pressure. To the residue was added ammonium hydroxide (5 mL, 25% w/v) and water (5 mL) with stirring, and the suspension was extracted with DCM(10 mL×4) The organic phase was washed with saturated brine and dried over anhydrous Na2SO4. The product 2b was obtained using flash chromatograph column eluted with PE : EA (5 : 1).
51%	With N-Bromosuccinimide; In acetonitrile; at 25℃; for 1.25h;	4.1.16 5-Bromo-8-aminoquinoline (21) To solution of compound 12 (1.0?g, 6.94?mmol) in 46.0?mL of acetonitrile, a portion of NBS (605?mg, 3.40?mmol) was added. The reaction mixture was stirred at 25?C for 15?min, then a second portion of NBS (667?mg, 3.75?mmol) was added. The reaction was stirred for 1?h?at 25?C. The solvent was evaporated under reduced pressure and the residue taken up with EtOAc and washed with water (3?*?50?mL). The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified by flash chromatography on silica gel (10% EtOAc in petroleum ether) to afford the title compound as an amorphous yellow solid (51% yield). 1H NMR (300?MHz, CDCl3) delta 8.76 (d, 1H, J?=?6.0?Hz), 8.43 (d, 1H, J?=?9.0?Hz), 7.56 (d, 1H, J?=?12.0), 7.48 (q, 1H, J?=?3.0?Hz), 6.80 (d, 1H, J?=?6.0?Hz); ESI-MS m/z 222.9 [M+H]+.
50%	With N-Bromosuccinimide; In acetone; at 20℃; for 0.5h;	Quinolin-8-amine (0.20 g, 1.38 muMol) was dissolved in acetonitrile (20 mL), and N-bromosuccinimide (0.26 g,1.43 muMol) was added to the solution. The mixture was stirred at room temperature for 30 minutes. Water was addedto the mixture. The organic layer was extracted with ethyl acetate, dried over anhydrous sodium sulfate, and concentratedunder reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate = 90/10-> 70/30) to obtain compound 117-1 (0.15 g, 50%).1H NMR (300 MHz, DMSO-d6, delta): 8.76 (d, J = 3.3 Hz, 1H), 8.42 (d, J = 8.1 Hz, 1H), 7.56 (d, J = 8.4 Hz, 1H), 7.48 (dd,J = 8.4, 4.2 Hz, 1H), 6.80 (d, J = 8.1 Hz, 1H), 5.04 (br, 2H).

	With N-Bromosuccinimide; In acetonitrile; for 0.75h;	INTERMEDIATE 7 5-BROMO-7-CHLOROQUINOLINEStep A. 8-Amino-5-bromoquinolineTo a solution of 8-aminoquinoline (4.0 g, 28 mmol) in CH3CN (185 mL) was added N-bromosuccinimide (2,47 g, 13.9 mmol). After stirring for 15 minutes, a second portion10 of N-bromosuccinimide (2.71 g, 15.2 mmol) was added. After stirring for an additional 30 minutes, the mixture was concentrated. The residue was dissolved in EtOAc, then washed with water (2 x 100 mL) and saturated NaCl (aq) (100 mL). The organics were dried over Na2SO4, filtered, then concentrated. The residue was purified by silica gel chromatography eluting with 10- 15% EtOAc/hexanes to afford the title compound as a white solid: 1H NMR (500 MHz,15 CDCl3): delta 8.79 (dd, J = 1.5, 4.1 Hz, IH), 8.46 (dd, J - 1.5, 8.5 Hz, IH), 7.60 (d, J = 8.1 Hz, IH), 7.52 (dd, J = 4.1, 8.5 Hz, IH), 6.83 (d, J = 8.1 Hz, IH); LC7: 2.48 min. (M+H) 225.
760 mg	With N-Bromosuccinimide; In acetonitrile; at 20℃; for 2h;	To a solution of 8-aminoquinoline (1 g, 4.8 mmol) in CH3CN (30 mL) were added NBS (1.28 g, 7.2 mmol). The reaction mixture was stirred at RT for 2 hour. The residue was treated with water and extracted with EA. The extracts were concentrated and the residue purifiled by silica gel chromatography to afford 5-bromo-8-quinolylamine (760 mg).

Reference： [1]Synthetic Communications,2019,vol. 49,p. 1406 - 1415
[2]European Journal of Medicinal Chemistry,2019,vol. 162,p. 290 - 320
[3]Patent: EP3401309,2018,A1 .Location in patent: Paragraph 0859
[4]Molecules,2019,vol. 24
[5]Patent: WO2010/30722,2010,A1 .Location in patent: Page/Page column 46
[6]Patent: WO2016/77240,2016,A2 .Location in patent: Page/Page column 90; 104

11
[ 53472-18-7 ]
[ 1215767-85-3 ]

Yield	Reaction Conditions	Operation in experiment
70%	With N-chloro-succinimide; In acetonitrile; at 75℃; for 12h;	To a solution of compound 21 (800?mg, 3.61?mmol) in 77.0?mL of acetonitrile, NCS (458?mg, 3.43?mmol) was added at 25?C. The reaction mixture was then stirred at 75?C for 12?h. After cooling to room temperature, acetonitrile was removed under reduced pressure. The residue was taken up with EtOAc, and washed with water (3?*?70?mL). The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified by flash chromatography on silica gel (7% EtOAc in petroleum ether) to afford the title compound as an amorphous orange solid (70% yield). 1H NMR (300?MHz, CDCl3) delta 8.78 (d, 1H, J?=?4.2?Hz), 7.69 (s, 1H), 8.43 (d, 1H, J?=?8.7?Hz), 7.50 (q, 1H, J?=?4.2), 5.46 (br, 2H); 13C NMR (75?MHz, CDCl3) delta 148.5, 148.4, 135.5, 133.0, 130.7, 127.4, 126.3, 122.3, 121.9. ESI-MS m/z 258.0 [M+H]+.
	With N-chloro-succinimide; In acetonitrile; at 75℃;	Step B. 8-Amino-5-bromo-7-chloroquinoline20 To a solution of <strong>[53472-18-7]8-amino-5-bromoquinoline</strong> (440 mg, 1 ,97 mmol) in CH3CN (39 mL) was added N-chlorosuccinimide (250 mg, 1.87 mmol). The mixture was stirred at 75"C until no further conversion of the starting material was observed by LC/MS and TLC analysis. The mixture was allowed to cool to room temperature then concentrated. The residue was dissolved in EtOAc, then washed with water (2 x 50 mL) then saturated NaCl (aq) (50 mL). The25 organic phase was dried over Na2SO4, filtered, then concentrated. The residue was purified by silica gel chromatography eluting with 15% EtOAc/hexanes to afford the title compound as a MRL DOB-00006solid: 1H NMR (500 MHz, CDCl3): 6 8.81 (dd, J = 1.4, 4.1 Hz, IH) 8.43 (dd, J = 1.4, 8.5 Hz, IH), 7.71 (s, IH), 7.51 (dd, J = 4.1, 8.5 Hz, IH); LC6: 4.27 rain. (M+H) 259.

Reference： [1]European Journal of Medicinal Chemistry,2019,vol. 162,p. 290 - 320
[2]Patent: WO2010/30722,2010,A1 .Location in patent: Page/Page column 46-47

12
[ 53472-18-7 ]
[ 69610-41-9 ]
[ 1470070-35-9 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium tris(acetoxy)borohydride; acetic acid; In 1,2-dichloro-ethane; at 20℃; for 18h;Inert atmosphere;	General procedure: A solution of N-Boc-(L)-proline (4.94 g, 23 mmol) inTHF (35 mL) was cooled to 0 under nitrogen, and BH3·DMS (4.38 mL, 46 mmol) was carefully added. The reaction mixture kept at 0 for an additional 5 h and then left to warm up overnight.Water (80 mL) was carefully added to quench the reaction. Ethyl acetate (500 mL) was added andthe organic phase was washed with brine (80 mL), saturated NaHCO3 aq. (80 mL), H2O (2×80 mL)and finally brine (80 mL). The organic phase was evaporated under reduced pressure to provide4.45g (96%) of the N-Boc-(L)-prolinol as a colorless oil that was used without purification. Thematerial gradually solidifies at room temperature.To a suspension of PCC (17.2 g, 80 mmol) in dry CH2Cl2 (120 mL) at room temperature wasslowly added a solution of the above N-Boc-(L)-prolinol (4.05 g, 20 mmol) in CH2Cl2 (145 mL).After stirring for 3 h at room temperature, ethyl ether (250 mL) was added to the reaction mixture,then kept stirring for an additional 0.5 h and filtered. The elution process was repeated thrice; thecombined ethyl ether layers were washed with brine (3×100 mL) and dried by Na2SO4,concentrated under reduced pressure to provide 3.72 g (93%) of the N-Boc-(L)-prolinal as acolorless oil that was used without purification.To a solution of the above N-Boc-(L)-prolinal (3.3 g, 15.2 mmol) in ClCH2CH2Cl (33 mL)was added amquine (10.1 mmol), ethylic acid (3.63 g, 60.4 mmol), then carefully added sodiumtriacetoborohydride (5.8 g, 27 mmol), the resulting mixture was stirred at room temperature underN2 for 18 h. Saturated NaHCO3 aq. (1 mL) was carefully added to quench the reaction. Themixture was extracted by ethyl acetate (3×50 mL), the combined organic layers were dried by K2CO3 and concentrated, further purification by flash chromatography on silica gel (1:15EtOAc/Hexane), gave the N-Boc-amide as a pale yellow oil.The above N-Boc-amide was dissolved in dry CH2Cl2 (150 mL), trifluoroacetic acid (40 mL)was added, the solution was stirred at room temperature for 3 h and then concentrated under reducedpressure to remove excess trifluoroacetic acid. The residue was dissolved in CH2Cl2 and the solutionwas extracted with water (3×50 mL). The aqueous phase was cooled (5 ), basified with NaOHpellets and extracted with CH2Cl2 (5×50 mL). The combined organic layers were dried (K2CO3),and concentrated under reduced pressure to provide the free amide as a clear colorless oil that was pure by H NMR and was used without further purification.

Reference： [1]Tetrahedron Letters,2014,vol. 55,p. 3255 - 3258

13
[ 67-56-1 ]
[ 53472-18-7 ]
[ 201230-82-2 ]
[ 1612247-58-1 ]

Yield	Reaction Conditions	Operation in experiment
	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; triethylamine; In N,N-dimethyl-formamide; at 70℃; for 15h;Sealed tube;	A solution <strong>[53472-18-7]5-bromoquinolin-8-amine</strong> (260 mg, 1.2 mmol) in DMF (4 mL) was placed in a sealed tube and degassed with carbon monoxide for 10 minutes. In a separate sealed tube, a solution of PdCl2(dppf) (85 mg, 0.12 mmol), triethylamine (490 iL, 3.5 mmol) in methanol (4 mL) was degassed with carbon monoxide for 10 minutes. The palladium solution was then added to the amine, placed under a balloon atmosphere of carbon monoxide and heated to 70 C for 15 hours. The cooled reaction was then filtered over a pad of CELITE and extracted from water using ethyl acetate. The organic layers were dried over sodium sulfate, filtered and concentrated in vacuo. The crude material was purified via MPLC (0-100% EtOAc/hexanes gradient) to afford methyl 8-aminoquinoline-5-carboxylate. LC-MS (IE, m/z): 203 [M + 1]+

Reference： [1]Patent: WO2014/85210,2014,A1 .Location in patent: Page/Page column 41

14
[ 53472-18-7 ]
[ 1612247-59-2 ]

Reference： [1]Patent: WO2014/85210,2014,A1

15
[ 53472-18-7 ]
[ 1612247-60-5 ]

Reference： [1]Patent: WO2014/85210,2014,A1

16
[ 53472-18-7 ]
4-methyl-N-(5-phenylquinolin-8-yl)benzenesulfonamide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2015,vol. 25,p. 5199 - 5202
[2]Patent: WO2016/25779,2016,A1

17
[ 53472-18-7 ]
N-(5-(furan-2-yl)quinolin-8-yl)-4-methylbenzenesulfonamide [ No CAS ]