[ CAS No. 433226-06-3 ] {[proInfo.proName]}

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2D 3D

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Quality Control of [ 433226-06-3 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 433226-06-3 ]

SDS Specification

Alternatived Products of [ 433226-06-3 ]

Product Details of [ 433226-06-3 ]

CAS No. :	433226-06-3	MDL No. :	MFCD08276943
Formula :	C₈H₉BrN₂O₂	Boiling Point :	No data available
Linear Structure Formula :	-	InChI Key :	QGADVECLXFPSOE-UHFFFAOYSA-N
M.W :	245.07	Pubchem ID :	18525957
Synonyms :

Calculated chemistry of [ 433226-06-3 ] Expand+

Physicochemical Properties

Num. heavy atoms :	13
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.25
Num. rotatable bonds :	3
Num. H-bond acceptors :	3.0
Num. H-bond donors :	1.0
Molar Refractivity :	52.43
TPSA :	65.21 ?2

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) :	-6.4 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.09
Log Po/w (XLOGP3) :	1.97
Log Po/w (WLOGP) :	1.61
Log Po/w (MLOGP) :	1.22
Log Po/w (SILICOS-IT) :	1.5
Consensus Log Po/w :	1.68

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.74
Solubility :	0.442 mg/ml ; 0.0018 mol/l
Class :	Soluble
Log S (Ali) :	-2.96
Solubility :	0.266 mg/ml ; 0.00108 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.0
Solubility :	0.242 mg/ml ; 0.000989 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.93

Safety of [ 433226-06-3 ]

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

Application In Synthesis of [ 433226-06-3 ]

* 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 [ 433226-06-3 ]

[ 433226-06-3 ] Synthesis Path-Downstream 1~16

1
[ 433226-06-3 ]
[ 140-88-5 ]
[ 941604-76-8 ]

Yield	Reaction Conditions	Operation in experiment
66%		An acetonitrile (100 tnL) solution of <strong>[433226-06-3]ethyl 2-amino-5-bromonicotinate</strong> (2.46 g, 10 mmol), ethyl acrylate (3.1 mL, 30 mmol) and diisopropylethylamine (5.3 mL, 30 mmol) was purged with Argon for 10 min. Pd(OAc)2 (225 mg, 1 mmol) and P(o-Tol)3 (609 rag, 2 mmol) was added and then the Argon purge was repeated. The mixture was heated to 100 0C and stirred for 4 hours under Argon. Upon cooling, the mixture was evaporated and purified by chromatography (silica, 1-2% MeOH in CH2CI2). Crystallization from a CH2Cl2 /hexane mixture afforded 1.73 g (66%) of the title compound. 1H NMR (300 MHz, CDCl3, delta) 8.36 and 8.33 (2 AA' d, J=2.3 Hz, 2H), 7.58 (d, J=16.0 Hz, IH), 6.32 (d, J=16.0 Hz, IH), 4.37 and 4.26 (2q, J=7.2 Hz, 2x2H), 1.42 and 1.34 (2t, J=7.2 Hz, 2x3H).

Reference： [1]Patent: WO2007/67416,2007,A2 .Location in patent: Page/Page column 64; 135

2
[ 13362-26-0 ]
[ 433226-06-3 ]

Yield	Reaction Conditions	Operation in experiment
100%	With N-Bromosuccinimide; In tetrahydrofuran; at 0 - 23℃; for 18h;	[0243] To a stirred solution of compound 11(15 g; 90.36 mmol; 1 eq) in dry THF (150 mL) was added NBS (16 g; 90.36 mmol; 1 eq) in portions at 0 C and the resulting mixture was stirred at 23 C for 18 h. The mixture was poured into ice-cold saturated aqueous NaHCO3 solution and the organic components were extracted with ethyl acetate (3 x 200 mL). The combined organic layers were then washed with brine solution, dried over anhydrous sodium sulfate, filtered and evaporated to dryness to afford the title compound (22 g, 100%) as an off white solid. 1H NMR (DMSO-d6) oe 8.29 (d, 1H, J = 3 Hz), 8.12 (d, 1H, J = 2 Hz), 7.31 (s, 2H), 4.29 (q, 2H, J = 7 Hz), 1.30 (t, 3H, J = 7 Hz). LCMS: mlz = 245.0 [M+j, 247.0 [M+21, RT = 3.34 minutes, (Program P1, Column W).
98.36%	With N-Bromosuccinimide; In acetonitrile; at 20℃; for 3h;	100 mmol (16.6 g) of ethyl 2-aminonicotinate was reacted with 110 mmol (19.58 g) of N-bromosuccinimide in 200 ml of acetonitrile and reacted at room temperature for three hours. After the completion of the reaction allow to stand for three hours at zero degrees Celsius environment . Suction filtration carried out , filter cake leaching with acetonitrile to obtain 24. 1g of solid, the yield of 98.36%. Acetonitrile spin recovery.
91%	With bromine; sodium hydrogencarbonate; In dichloromethane; at 0℃; for 1h;	A CH2Cl2 (30 mL) solution of bromine (16.8Og, 105 mmol) was added to a CH2Cl2 (ISO mL) suspension of ethyl <2-aminonicotinate (11.64 g, 70 mmol) and NaHCO3 (17.7 g, 210 mmol) at 0 0C. After an hour stirring at this temperature, water (50 mL) was added. The solution was decolorized with a saturated solution OfNaHSO3, extracted with CH2Cl2, dried over MgSO4 and evaporated. Recrystallization from a CH2Cl2 /hexane mixture afforded 16.02 g (91%) of the title compound. 1H NMR (300 MHz, CDCl3, delta) 8.22 (m, 2H), 4.35 (q, J=7.2 Hz, 2H), 1.39 (t, J=7.2 Hz, 3H). MS (ESI) m/e 245 (M + H)+.

	With N-Bromosuccinimide;	Example 125 Synthesis of ethyl 2-amino-5-bromonicotinate. To a solution of ethyl 2-aminonicotinate (25 g, 150.44 mmol) in CH3CN (500 mL) was added NBS (32.1 g, 180.5 mmol) in portions over 30 min at 0 C. The mixture was warmed to RT and stirred for 2 h. The reaction mixture was concentrated. The residue was washed with NaHCO3 aqueous (300 mL) and extracted with EtOAc (300 mL*3), the combined organic layers were concentrated to give ethyl 2-amino-5-bromonicotinate (36.9 g, yield: 100%) as a yellow solid, which was used in the next step without further purification. ESI-MS [M+H]+: 245.1.
	With N-Bromosuccinimide;	Example 71 Synthesis of ethyl 2-amino-5-bromonicotinate. To a solution of ethyl 2-aminonicotinate (500 mg, 3.00 mmol) in dry MeCN (20 mL) was added NBS (643 mg, 3.6 mmol) slowly at RT. The resulting mixture was stirred at RT for 1 h. The reaction was then quenched with H2O (30 mL) and extracted with EtOAc (30 mL*3). The combined organic layers were washed with brine, dried over Na2SO4, and concentrated in vacuo to give the crude product of ethyl 2-amino-5-bromonicotinate (700 mg, yield: 95.2%) as a white solid, which was used in the next step without purification. ESI-MS [M+H]+: 245.0.

Reference： [1]Patent: WO2015/95128,2015,A1 .Location in patent: Paragraph 0239; 0242; 0243
[2]European Journal of Medicinal Chemistry,2018,vol. 158,p. 236 - 246
[3]Patent: CN104402881,2016,B .Location in patent: Paragraph 0022; 0023
[4]Patent: WO2007/67416,2007,A2 .Location in patent: Page/Page column 64; 134
[5]Patent: US2019/284182,2019,A1
[6]Patent: US2019/284182,2019,A1

Yield	Reaction Conditions	Operation in experiment
78%	With lithium hydroxide; In dimethyl sulfoxide; at 120℃; for 1h;Inert atmosphere; Sealed tube;	General procedure: In a 10mL dry sealed reaction tube,Add ethyl 1,2,3-triazine-5-carboxylate 3a (15.3mg, 0.10mmol), ethyl cyanoacetate 2b (13.6mg, 0.12mmol) and lithium hydroxide (0.5mg, 0.02mmol) in this order . The solvent nitrogen was added DMSO (1.0mL) was substituted three times, the reaction tube was sealed was placed 120 reaction 1h. The reaction was monitored by TLC. After the reaction was completed, it was extracted with dichloromethane (3 * 10 mL). The organic phase was dried over anhydrous sodium sulfate and concentrated in vacuo. After column chromatography, the target product 13c (16.0 mg, 67%) was obtained.

4
[ 6165-69-1 ]
[ 433226-06-3 ]
[ 1216772-00-7 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2010,vol. 18,p. 707 - 718

5
[ 433226-06-3 ]
[ 250726-93-3 ]
[ 1216772-02-9 ]