114078-88-5|5-Bromo-1,2,3-triazine| Ambeed

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Quality Control of [ 114078-88-5 ] Purity: 97% SDS Specification

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Product Details of [ 114078-88-5 ]

CAS No. :	114078-88-5
Formula :	C₃H₂BrN₃
M.W :	159.97
SMILES Code :	BrC1=CN=NN=C1
MDL No. :	MFCD13193660
InChI Key :	LSBKXRBABHPHBW-UHFFFAOYSA-N
Pubchem ID :	13905235

Safety of [ 114078-88-5 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302
Precautionary Statements:	P280-P305+P351+P338

Computational Chemistry of [ 114078-88-5 ] Show Less

Physicochemical Properties

Num. heavy atoms	7
Num. arom. heavy atoms	6
Fraction Csp3	0.0
Num. rotatable bonds	0
Num. H-bond acceptors	3.0
Num. H-bond donors	0.0
Molar Refractivity	27.53
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	38.67 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.44
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	-0.01
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	0.63
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.	0.3
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	1.49
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	0.77

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-1.46
Solubility	5.55 mg/ml ; 0.0347 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-0.35
Solubility	71.0 mg/ml ; 0.444 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	-2.12
Solubility	1.21 mg/ml ; 0.00759 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.	-7.28 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	2.0
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)	1.68

Application In Synthesis of [ 114078-88-5 ]

* 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 [ 114078-88-5 ]

[ 114078-88-5 ] Synthesis Path-Downstream 1~21

1
[ 3994-46-5 ]
[ 114078-88-5 ]
[ 114078-89-6 ]

References: [1]Chemical and pharmaceutical bulletin,1988,vol. 36,p. 3838 - 3848.
[2]Chemical and pharmaceutical bulletin,1987,vol. 35,p. 3952 - 3954.

2
[ 122481-11-2 ]
[ 114078-88-5 ]

Yield	Reaction Conditions	Operation in experiment
8.8 g	With sodium periodate; In dichloromethane; water; at 0℃; for 12.0h;	One step up the crude was added methylene chloride (200 mL) and water (76 mL), cooled to 0 , sodium periodate (29.4g, 137mmol) with stirring. After the addition was complete the reaction was stirred for 12 hours 0 . Warmed to 25 , liquid separation, the aqueous phase was extracted with dichloromethane (100mL × 3), the organic phases were combined, saturated brine (250mL), dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated and the crude product was purified by silica gel column chromatography (petroleum ether: ethyl acetate = 10: 1) gave the title compound as a white solid (8.8g, yield 73.5% in two steps).
710 mg	With sodium periodate; In dichloromethane; water; at 20℃; for 16.0h;	To a solution of compound S2 (1 g, crude) in DCM (15 mL) and water (5 mL) was added NaIO4(2 g, 9.3 mmol). The reaction was stirred at room temperature for 16 hrs. The mixture was diluted with DCM and washed with water, brine, dried over anhydrous Na2SO4, filtered, and concentrated. The residue was purified by silica gel column (eluted with EtOAc/PE=1/5) to give the title compound (710 mg, 65.2% yield) as a purple solid.
	With sodium periodate; In dichloromethane; water; at 0℃; for 4.0h;	A solution of crude 4-bromopyrazol-l-amine (20.0 g, crude) in DCM (500 mL) and water (200 mL) was cooled to 0 C. To the solution was added NaI04 (52.8 g, 246.93 mmol). The resulting mixture was stirred at 0 C for 4 hrs and extracted with DCM (100 mL) for three times. The combined organic layer was washed with brine (100 mL), dried over anhydrous Na2S04 and concentrated in vacuo to give 5-bromotriazine (20.0 g) as brown solid, which was used in next step directly without any further purification

References: [1]Liebigs Annalen der Chemie,1993,p. 367 - 374.
[2]Chemical and pharmaceutical bulletin,1988,vol. 36,p. 3838 - 3848.
[3]Journal of the American Chemical Society,2011,vol. 133,p. 12285 - 12292.
[4]Patent: CN105884752,2016,A .Location in patent: Paragraph 0211; 0212; 0213.
[5]Patent: WO2017/35353,2017,A1 .Location in patent: Paragraph 0928.
[6]Patent: WO2018/83136,2018,A1 .Location in patent: Page/Page column 19; 20.

3
[ 7148-07-4 ]
[ 114078-88-5 ]
3-bromo-6,7-dihydro-5H-cyclopenta[b]pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
36%	In chloroform; at 45℃; for 1.0h;	To a solution of <strong>[114078-88-5]5-bromo-1,2,3-triazine</strong> (25 g, 156 mmol, 1.0 equiv) in CHCl3 (500 mL) was added 1-(cyclopent-1-en-1-yl)pyrrolidine (25.8 g, 188 mmol, 1.1 equiv). The mixture was stirred at 45 oC for 1 h, diluted with DCM (500 mL), washed with brine (300 mL) twice, dried over anhydrous sodium sulfate, concentrated under reduced pressure, and purified by silica gel chromatography (EA/PE, 10/90) to give 11 g (36%) of 3-bromo- 5H,6H,7H-cyclopenta[b]pyridine as a brown solid.
34.2%	In chloroform; at 0 - 45℃; for 0.833333h;	Weigh <strong>[114078-88-5]5-bromo-1,2,3-triazine</strong> (4.4g, 27.5mmol) was dissolved in chloroform (40 mL), and cooled to 0 deg.] C, was added 1-(cyclopentan-1-en-1-yl)pyrrolidine with stirring -1 After the addition, the reaction mixture was stirred at 0 C for 5 minutes, and raised to 45 C for 45 minutes. The crude product was purified by column chromatography on silica gel (petroleum ether: ethyl acetate = 5: 1 (1: 1) ) to give the title compound (1.86g, yield 34.2%).
34.3%	In chloroform; at 45℃; for 16.0h;	To a solution of compound S3 (400 mg, 2.5 mmol) in CHCl3(10 mL) was added 1-(cyclopent-1-en-1-yl)pyrrolidine (516 mg, 3.8 mmol). The reaction was stirred at 45 C. for 16 hrs. The reaction mixture was diluted with DCM and washed water, brine, dried over anhydrous Na2SO4, filtered, and concentrated. The residue was purified by silica gel column (eluted with EtOAc/PE=1/10) to give the title compound (170 mg, 34.3% yield) as a gray solid.

References: [1]Journal of the American Chemical Society,2011,vol. 133,p. 12285 - 12292.
[2]Patent: WO2019/144041,2019,A1 .Location in patent: Paragraph 0204.
[3]Patent: CN105884752,2016,A .Location in patent: Paragraph 0214; 0215; 0216.
[4]Patent: WO2017/35353,2017,A1 .Location in patent: Paragraph 0929.

4
[ 52313-50-5 ]
[ 114078-88-5 ]
[ 1240601-78-8 ]