[ CAS No. 959558-28-2 ] {[proInfo.proName]}

Name: 959558-28-2|4-Bromo-2,7-naphthyridin-1-amine|97%
Brand: Ambeed
SKU: A106217
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2D 3D

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Quality Control of [ 959558-28-2 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 959558-28-2 ]

SDS Specification

Alternatived Products of [ 959558-28-2 ]

Product Details of [ 959558-28-2 ]

CAS No. :	959558-28-2	MDL No. :	MFCD14707654
Formula :	C₈H₆BrN₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	GIFGLLRPNLFCGT-UHFFFAOYSA-N
M.W :	224.06	Pubchem ID :	23727075
Synonyms :

Calculated chemistry of [ 959558-28-2 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	10
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	51.64
TPSA :	51.8 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.69 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.43
Log Po/w (XLOGP3) :	1.38
Log Po/w (WLOGP) :	1.98
Log Po/w (MLOGP) :	1.13
Log Po/w (SILICOS-IT) :	1.89
Consensus Log Po/w :	1.56

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.72
Solubility :	0.432 mg/ml ; 0.00193 mol/l
Class :	Soluble
Log S (Ali) :	-2.07
Solubility :	1.9 mg/ml ; 0.00849 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.83
Solubility :	0.0332 mg/ml ; 0.000148 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.72

Safety of [ 959558-28-2 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H317-H319	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 959558-28-2 ]

* 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 [ 959558-28-2 ]
Downstream synthetic route of [ 959558-28-2 ]

[ 959558-28-2 ] Synthesis Path-Upstream 1~2

1
[ 27225-00-9 ]
[ 959558-28-2 ]

Yield	Reaction Conditions	Operation in experiment
18.5 g	at 20 - 25℃; for 1 h;	4-Bromo-2,7-naphthyridin-1-ylamine 32 g of 2,7-naphthyridin-1-ylamine is dissolved in 200 ml of acetic acid at room temperature. 35 g of bromine in 200 ml of acetic acid are then added slowly that the temperature does not exceed 25°. The mixture is stirred for a further 60 minutes.The suspension obtained is dissolved in 500 ml of water, and the pH is adjusted to pH 7-8 using 500 ml of 25percent aqueous ammonia solution.The mixture is stirred for 14 h. The brown precipitate is filtered off, washed with water and dried, giving 28.3 g of crude product. Purification by flash chromatography in ethyl acetate/methanol gives 18.5 g of 4-bromo-2,7-naphthyridin-1-ylamine, M224.06 g/mol, M+H found 224.

Reference： [1] Patent: US2015/252041, 2015, A1, . Location in patent: Paragraph 0167; 0168; 0169

2
[ 5444-01-9 ]
[ 959558-28-2 ]

Reference： [1] Patent: US2015/252041, 2015, A1,

[ 959558-28-2 ] Synthesis Path-Downstream 1~8

1
[ 959558-28-2 ]
[ 1323919-50-1 ]
[ 1323917-72-1 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydrogencarbonate;bis-triphenylphosphine-palladium(II) chloride; In water; N,N-dimethyl-formamide; at 80℃;Inert atmosphere;	EXAMPLE 32: Synthesis of 4-[2-(2-fluoro-phenyl)-[1 ,8]naphthyridin-4-yl]-[2,7]naphthyridin- 1- C/MS: 1.40, [M+H] 368

Reference： [1]Patent: WO2011/95196,2011,A1 .Location in patent: Page/Page column 115
[2]Patent: US2012/295902,2012,A1 .Location in patent: Paragraph 0426

2
[ 959558-28-2 ]
[ 1323919-50-1 ]
[ 1323917-74-3 ]

Reference： [1]Patent: WO2011/95196,2011,A1
[2]Patent: US2012/295902,2012,A1

3
[ 27225-00-9 ]
[ 959558-28-2 ]

Yield	Reaction Conditions	Operation in experiment
18.5 g	With bromine; acetic acid; at 20 - 25℃; for 1.0h;	4-Bromo-2,7-naphthyridin-1-ylamine32 g of 2,7-naphthyridin-1-ylamine is dissolved in 200 ml of acetic acid at room temperature. 35 g of bromine in 200 ml of acetic acid are then added slowly that the temperature does not exceed 25. The mixture is stirred for a further 60 minutes.The suspension obtained is dissolved in 500 ml of water, and the pH is adjusted to pH 7-8 using 500 ml of 25% aqueous ammonia solution.The mixture is stirred for 14 h. The brown precipitate is filtered off, washed with water and dried, giving 28.3 g of crude product. Purification by flash chromatography in ethyl acetate/methanol gives 18.5 g of 4-bromo-2,7-naphthyridin-1-ylamine, M224.06 g/mol, M+H found 224.

Reference： [1]Patent: US2015/252041,2015,A1 .Location in patent: Paragraph 0167; 0168; 0169

4
[ 943324-08-1 ]
[ 959558-28-2 ]
4-(2-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-2,7-naphthyridin-1-ylamine [ No CAS ]

Reference： [1]Patent: US2015/252041,2015,A1

5
[ 5444-01-9 ]
[ 959558-28-2 ]

Reference： [1]Patent: US2015/252041,2015,A1

6
[ 943324-08-1 ]
[ 959558-28-2 ]
4-(1-benzenesulfonyl-2-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-2,7-naphthyridin-1-ylamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium phosphate; (bis(tricyclohexyl)phosphine)palladium(II) dichloride; In diethylene glycol dimethyl ether; water; at 20 - 125℃; for 23.5h;	4-(1-Benzenesulfonyl-2-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-2,7-naphthyridin-1-ylamine23.7 g of tripotassium phosphate and 3.2 g of trans-dichlorobis(tricyclohexyl-phosphine)palladium(II) are added to a solution of 12.5 g of <strong>[959558-28-2]4-bromo-2,7-naphthyridin-1-ylamine</strong> in 400 ml of diglyme and 15 ml of water. The mixture is heated to 125, and 25 g of 1-(benzenesulfonyl)-2-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine in 100 ml of diglyme are added dropwise over the course of 30 minutes. The mixture is stirred at 125 for 3 h, at room temperature for 20 h and the solvent is subsequently removed and the mixture is subjected to conventional work-up. The product is purified by means of flash chromatography over 330 g of silica with a methanol gradient in ethyl acetate with 200 ml/min with UV detection at 254 nm, giving a pure fraction (5.1 g) and a contaminated fraction (6.5 g) of 4-(1-benzenesulfonyl-2-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-2,7-naphthyridin-1-ylamine, M415.47 g/mol, M+H found 416.

Reference： [1]Patent: US2015/252041,2015,A1 .Location in patent: Paragraph 0174; 0175

7
[ 959558-28-2 ]
C₂₁H₂₁F₃N₄O [ No CAS ]
5-((1-amino-2,7-naphthyridin-4-yl)ethynyl)-N-(4-((4-methylpiperazin-1-yl)methyl)-3-(trifluoromethyl)phenyl)nicotinamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
35%	With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine; triphenylphosphine; In N,N-dimethyl-formamide; at 55℃; for 12.0h;Inert atmosphere;	A solution of Bromo compound 6a (100 mg, 0.45 mmol, 1.2 equiv), Pd(PPh3)4 (10 mol%), CuI (5 mol%) and Triphenylphosphine (10 mg) in Triethylamine (1.5 mL) was de-oxygenated using steam of Argon gas. A de-oxygenated solution of alkyne 2b (150 mg, 0.37 mmol, 1 equiv) in DMF (4 mL) was added slowly over a period of 10 min to the solution and the reaction temperature was increased to 55 C and allowed to stir 12 h. The reaction was diluted with ethyl acetate (300 mL). The organic layer was washed with water (5 × 50 mL), saturated NH4Cl (1 × 50 mL) and washed with brine (1 × 50 mL). Combined organic layers were dried over anhydrous sodium sulphate, filtered and concentrated in vacuo. The pure product 16 was obtained by flash column chromatography. Yield = 35%; TLC Rf = 0.1 (10 % MeOH/CH2Cl2) 1H NMR (500 MHz, DMSO-d6) delta 10.77 (s, 1H), 9.60 (s, 1H), 9.05 (d, J = 2.2 Hz, 1H), 9.00 (d, J = 2.0 Hz, 1H), 8.73 (d, J = 5.7 Hz, 1H), 8.54 (t, J = 2.1 Hz, 1H), 8.38 (s, 1H), 8.20 (s, 1H), 8.04 (d, J = 9.9 Hz, 1H), 7.96 (d, J = 5.7 Hz, 1H), 7.93 (s, 2H), 7.73 (s, 1H), 3.57 (s, 2H), 2.39 (s, 8H), 2.17 (s, 3H); 13C NMR (126 MHz, DMSO) delta 164.06, 158.62, 154.11, 152.24, 149.60, 148.90, 148.03, 140.47, 138.31, 137.37, 132.96, 131.83, 130.34, 128.86, 124.01, 120.21, 117.56, 112.05, 100.80, 90.37, 89.95, 57.87, 55.11, 53.02, 46.03; HRMS (ESI+): calcd. for C29H27F3N7O (MH+) 546.2224, found 546.2221

Reference： [1]Bioorganic Chemistry,2019,vol. 90

8
[ 959558-28-2 ]
C₂₂H₂₃F₃N₄O [ No CAS ]
5-((1-amino-2,7-naphthyridin-4-yl)ethynyl)-6-methyl-N-(4-((4-methylpiperazin-1-yl)methyl)-3-(trifluoromethyl)phenyl)nicotinamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
49%	With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine; triphenylphosphine; In N,N-dimethyl-formamide; at 50℃; for 12.0h;Inert atmosphere;	A solution of Bromo compound 6a (96 mg, 0.43 mmol, 1.2 equiv), Pd(PPh3)4 (10 mol%), CuI (5 mol%) and Triphenylphosphine (10 mg) in Triethylamine (1.5 mL, 10.8 mmol, 30 equiv) was de-oxygenated using steam of Argon gas. A de-oxygenated solution of alkyne 3b (150 mg, 0.36 mmol, 1 equiv) in DMF (4 mL) was added slowly over a period of 10 min to the solution and the reaction temperature was increased to 50 C and allowed to stir 12 h. The reaction was quenched by addition of NH4Cl (5 mL) at room temperature and diluted with ethyl acetate (300 mL). The organic layer was washed with water (5 × 50 mL) and washed with brine (1 × 50 mL). Combined organic layers were dried over anhydrous sodium sulphate, filtered and concentrated in vacuo. The pure product 15 was obtained by flash column chromatography. Yield = 49%.; TLC Rf = 0.1 (10 % MeOH/CH2Cl2). 1H NMR (500 MHz, DMSO-d6) delta 10.65 (s, 1H), 9.60 (s, 1H), 8.93 (s, 1H), 8.74 (d, J = 5.7 Hz, 1H), 8.48 (s, 1H), 8.39 (s, 1H), 8.18 (s, 1H), 8.03 (d, J = 8.5 Hz, 1H), 7.92 (s, 2H), 7.88 (d, J = 5.7 Hz, 1H), 7.70 (d, J = 8.5 Hz, 1H), 3.55 (s, 2H), 2.80 (s, 3H), 2.37 (s, 8H), 2.14 (s, 3H); 13C NMR (126 MHz, DMSO) delta 164.01, 162.28, 158.58, 152.20, 149.63, 148.92, 147.44, 140.37, 138.34, 137.81, 132.86, 131.74, 127.93, 127.77, 123.97, 118.86, 117.71, 117.37, 112.05, 101.07, 92.66, 90.47, 57.90, 55.19, 53.17, 46.19, 24.28; HRMS (ESI+): calcd. for C30H29F3N7O (MH+) 560.2380, found 560.2380

Reference： [1]Bioorganic Chemistry,2019,vol. 90

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H200	Unstable explosive
H201	Explosive; mass explosion hazard
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Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 959558-28-2 ] {[proInfo.proName]}

Quality Control of [ 959558-28-2 ]

Related Doc. of [ 959558-28-2 ]

Product Details of [ 959558-28-2 ]

Calculated chemistry of [ 959558-28-2 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 959558-28-2 ]

Application In Synthesis of [ 959558-28-2 ]

[ 959558-28-2 ] Synthesis Path-Upstream 1~2

[ 959558-28-2 ] Synthesis Path-Downstream 1~8

Related Functional Groups of [ 959558-28-2 ]

Bromides

Amines

Related Parent Nucleus of [ 959558-28-2 ]

Naphthyridines

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Related Functional Groups of
[ 959558-28-2 ]

Related Parent Nucleus of
[ 959558-28-2 ]