944709-42-6|6,8-Dibromo-[1,2,4]triazolo[1,5-a]pyrazine| Ambeed

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Quality Control of [ 944709-42-6 ] Purity: 98% SDS Specification

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Product Details of [ 944709-42-6 ]

CAS No. :	944709-42-6
Formula :	C₅H₂Br₂N₄
M.W :	277.90
SMILES Code :	BrC2=C[N]1C(=NC=N1)C(=N2)Br
MDL No. :	MFCD09701977
InChI Key :	KUILFTQAMHFSPW-UHFFFAOYSA-N
Pubchem ID :	44630666

Safety of [ 944709-42-6 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H332-H335
Precautionary Statements:	P261-P280-P305+P351+P338

Computational Chemistry of [ 944709-42-6 ] Show Less

Physicochemical Properties

Num. heavy atoms	11
Num. arom. heavy atoms	9
Fraction Csp3	0.0
Num. rotatable bonds	0
Num. H-bond acceptors	3.0
Num. H-bond donors	0.0
Molar Refractivity	46.18
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	43.08 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.82
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	1.73
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.65
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.	1.34
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	1.44
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.6

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.26
Solubility	0.153 mg/ml ; 0.000552 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.	-2.25
Solubility	1.56 mg/ml ; 0.00561 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	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	-3.04
Solubility	0.252 mg/ml ; 0.000906 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	Yes
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.	-6.77 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	0.0
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<0.0
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)	2.35

Application In Synthesis of [ 944709-42-6 ]

* 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 [ 944709-42-6 ]

[ 944709-42-6 ] Synthesis Path-Downstream 1~35

1
[ 22246-76-0 ]
[ 944709-42-6 ]
8-((6-bromo-[1,2,4]triazolo[1,5-a]pyrazin-8-yl)amino)-4,5-dihydro-1H-benzo[b]azepin-2(3H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
56%	With N-ethyl-N,N-diisopropylamine; In isopropyl alcohol; for 24h;Reflux;	General procedure: To a solu&et of 6,S-dlbrornci- [l,2,4J So[1,5-&yrathE (0.21 0.72] rtuuol, Ark Pliant) and 5- anth4th-1Herr]-an-Z3hJrE (0.12 g, 0.7?2 numi, Astatecl irue-PrOH (S ruL) was added DEA (0377 niL, 2.16 rtutvl). The nixthrr was heated to reflux for abat 24 k The resu1iir so]u&nwas cooled to it and filtered to give 8-((b-[L24kcc[LJvrath8- yVn&-45thkv&c?-JH-bo(bJ?zn?in-2(3Scv2e (0.15 g, 55percent) as a brtwn solid: ?H NMR (DM5 0-dEl) oe 9.62 (s, 1H), S.69 (s, lH 5S9 (s, 1H), 7.61-7.67 (ii,, 2H), 723(d, frS.4 H; 1H), 2.65 Qt, 1=6.4 H; 2H 2.07-2. 15 (m, 3H 1.23 (rr 1H).

References: [1]Patent: WO2015/157955,2015,A1 .Location in patent: Page/Page column 54.

2
[ 944709-42-6 ]
[ 69843-13-6 ]
6-bromo-N-(1-methyl-1H-pyrazol-4-yl)-[1,2,4]triazolo[1,5-a]pyrazin-8-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%		To amixthxe of NaIl (0264 g, &F?4 35 nol) inTEF (50 nL)was added l-methyl-lH-pyrazd-4- amine (2Q97 g, 21.59 nunol). The niixiui was sthmd thrabc?at0.5 hat thc?at 0 C. A so1niiciof (5 g, 17S9 nunDl7 Aik Plmnn) iii TEF C30 iuL)was added slowlyardtlE leacthnnuetnewas siinedforlkat0t. Water(SmL)was a&Ied.Themixtur? was conetted to drjne. Adth&nal two reaction nuethrEs weze set up follcwing the above nitIiri1. All tluee batches were contimd, wa±er (109 mL) was added. The nuetm was extaDted with ECAc (3 x 5J0 niL).The orgaiiic pluse wa diied over NaSOi, comeitated urder iethixed piessuxe, parified ?ue silica gel ci ntognphyebath with 2S5]percent ECAc WE to give Cbvm9-N (J-ty1-SH-pwcroy1flL24]mo[L5-Q1yrc8-ani (12 g, 7A) as a wlite solid: ?H NMR (411 MH; DMSO-D6) 8 ppxw5 10.71 (s, 1H), 8.59-8.56 (d, J 12, 2H), 8i]7 (s, lii), 7.76 (, 1ff), 3.&5 (s, 3H).

References: [1]Patent: WO2015/157955,2015,A1 .Location in patent: Page/Page column 88; 89.

3
[ 944709-42-6 ]
tert-butyl 3-(8-(1-methyl-1H-pyrazol-4-ylamino)-[1,2,4]triazolo[1,5-a]pyrazin-6-yl)2,5-dihydro-1H-pyrrole-1-carboxylate [ No CAS ]

References: [1]Patent: WO2015/157955,2015,A1 .

4
[ 944709-42-6 ]
tert-butyl 3-(8-(1-methyl-1H-pyrazol-4-ylamino)-[1,2,4]triazolo[1,5-a]pyrazin-6-yl)pyrrolidine-1-carboxylate [ No CAS ]

References: [1]Patent: WO2015/157955,2015,A1 .

5
[ 944709-42-6 ]
(S)-tert-butyl 3-(8-(1-methyl-1H-pyrazol-4-ylamino)-[1,2,4]triazolo[1,5-a]pyrazin-6-yl)pyrrolidine-1-carboxylate [ No CAS ]
(R)-tert-butyl 3-(8-(1-methyl-1H-pyrazol-4-ylamino)-[1,2,4]triazolo[1,5-a]pyrazin-6-yl)pyrrolidine-1-carboxylate [ No CAS ]

References: [1]Patent: WO2015/157955,2015,A1 .

6
[ 944709-42-6 ]
(S)-N-(1-methyl-1H-pyrazol-4-yl)-6-(pyrrolidin-3-yl)-[1,2,4]triazolo[1,5-a]pyrazin-8-amine [ No CAS ]

References: [1]Patent: WO2015/157955,2015,A1 .

7
[ 944709-42-6 ]
(S)-1-(3-(8-((1-methyl-1H-pyrazol-4-yl)amino)-[1,2,4]triazolo[1,5-a]pyrazin-6-yl)pyrrolidin-1-yl)prop-2-en-1-one [ No CAS ]

References: [1]Patent: WO2015/157955,2015,A1 .

8
[ 944709-42-6 ]
tert-butyl 3-(8-((2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepin-8-yl)amino)-[1,2,4]triazolo[1,5-a]pyrazin-6-yl)2,5-dihydro-1H-pyrrole-1-carboxylate [ No CAS ]

References: [1]Patent: WO2015/157955,2015,A1 .

9
[ 944709-42-6 ]
tert-butyl 3-(8-((2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepin-8-yl)amino)-[1,2,4]triazolo[1,5-a]pyrazin-6-yl)pyrrolidine-1-carboxylate [ No CAS ]

References: [1]Patent: WO2015/157955,2015,A1 .

10
[ 461-17-6 ]
[ 944709-42-6 ]
6-bromo-8-(4,4,4-trifluorobutyl)-[1,2,4]triazolo[1,5-a]pyrazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Into a flask, under an inert atmosphere of nitrogen, was placed 1,1,1-trifluoro-4-iodobutane (6.7 g, 28 mmol), zinc metal (3.7 g, 56 mmol) and DMA (10 mL). This was followed by the dropwise addition of a solution of iodine (0.33 g, 1.3 mmol) in DMA (0.5 mL). The resulting mixture was stirred for 3 h at 80°C. The reaction was cooled and directly used in the next step. Into a flask, under an inert atmosphere of nitrogen, was placed <strong>[944709-42-6]6,8-dibromo-[1,2,4]triazolo[1,5-a]pyrazine</strong> (6.0 g, 22 mmol), Pd(PPh3)2Cl2 (0.91 g, 1.3 mmol) and THF (80 mL). The resulting mixture was allowed to stir for 1 h at RT. The intermediate from Step A (11 mL, 28 mmol) was added and the resulting solution was stirred for 16 h at RT. The reaction was quenched by the addition of sat. aq. NH4Cl. The resulting solution was extracted with EtOAc (3X) and the organic layers were combined, washed with brine, dried over anhydr. Na2SO4, and filtered. The filtrate was conc. in vacuo to dryness. The residue purified by silica gel chromatography with EtOAc:petroleum ether (0-20percent) to afford the title compound.

References: [1]Patent: WO2017/200857,2017,A1 .Location in patent: Page/Page column 103.

11
[ 944709-42-6 ]
8-(4,4,4-trifluorobutyl)-[1,2,4]triazolo[1,5-a]pyrazine-6-carbonitrile [ No CAS ]

References: [1]Patent: WO2017/200857,2017,A1 .

12
[ 944709-42-6 ]
8-(4,4,4-trifluorobutyl)-[1,2,4]triazolo[1,5-a]pyrazine-6-carboximidamide [ No CAS ]

References: [1]Patent: WO2017/200857,2017,A1 .

13
[ 944709-42-6 ]
4-amino-5-cyclopropyl-2-(8-(4,4,4-trifluorobutyl)-[1,2,4]triazolo[1,5-a]pyrazin-6-yl)-5-(5-(trifluoromethyl)pyridin-2-yl)-5H-pyrrolo[2,3-d]pyrimidin-6(7H)-one [ No CAS ]

References: [1]Patent: WO2017/200857,2017,A1 .

14
[ 944709-42-6 ]
(R)-4-amino-5-cyclopropyl-2-(8-(4,4,4-trifluorobutyl)-[1,2,4]triazolo[1,5-a]pyrazin-6-yl)-5-(5-(trifluoromethyl)pyrimidin-2-yl)-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one [ No CAS ]

References: [1]Patent: WO2017/200857,2017,A1 .

15
(3-fluorobenzyl)zinc(II) bromide [ No CAS ]
[ 944709-42-6 ]
6-bromo-8-(3-fluorobenzyl)-[1,2,4]triazolo[1,5-a]pyrazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With bis-triphenylphosphine-palladium(II) chloride; chloro-trimethyl-silane; at 20℃; for 16h;Inert atmosphere;	Into a flask under an. inert atmosphere of N2, were placed <strong>[944709-42-6]6,8-dibromo-[1,2,4]triazolo[1,5-a]pyrazine</strong> (6.0 g, 21.6mmol) and bis(triphenylphosphine)palladium(II) dichloride (1.5 g, 2.2 mmol). To this was added the zinc reagent from Step A, and the mixture was stirred at RT for 16 h. The mixture was quenched by the addition of sat. aq. NH4C1 (200 mL), and extracted with EtOAc (3 x 100 mL). The combined organic layer was dried over anhydr. Na2SO4, filtered and the filtrate was concentrated in vacuo to dryness. The residue was purified by column chromatography withEtOAc/petroleum ether (1/5) to afford the title compound.

References: [1]Patent: WO2017/197555,2017,A1 .Location in patent: Page/Page column 68.

16
(cyclohexylmethyl)zinc(II)iodide [ No CAS ]
[ 944709-42-6 ]
6-bromo-8-(cyclohexylmethyl)imidazo[1,2-a]pyrazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Into a flask under an inert atmosphere of N2, were placed 6,8-dibromoimidazo[1,2-a]pyrazine (4 g, 14.44 mmol), bis(triphenylphosphine)palladium(II) dichloride (1.01 g, 1.444 mmol) and THF (120 mL). The resulting mixture was stirred at RT for 1 h before the zinc reagent solution from Step Awas added dropwise at 0 °C. The resulting mixture was stirred at RT for 16 h then quenched by the addition of sat. aq. NH4C1 (400 mL). The resulting mixture was extracted with EtOAc (3 x 200 mL). The combined organic layer was washed with brine (2 x 500 mL), dried over anhydr. Na2SO4, filtered and the filtrate was concentrated in vacuo to dryness. The residue was purified by column chromatography with EtOAc/petroleum ether (5percent-45percent) to afford thetitle compound.

References: [1]Patent: WO2017/197555,2017,A1 .Location in patent: Page/Page column 69.

17
[ 944709-42-6 ]
6-(cyclohex-1-en-1-yl)-N-(1H-pyrazol-4-yl)-[1,2,4]triazolo[1,5-a]pyrazin-8-amine [ No CAS ]