1109284-33-4|6-Bromo-3-iodopyrazolo[1,5-a]pyrimidine| Ambeed

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Quality Control of [ 1109284-33-4 ] Purity: 97% SDS Specification

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Product Details of [ 1109284-33-4 ]

CAS No. :	1109284-33-4
Formula :	C₆H₃BrIN₃
M.W :	323.92
SMILES Code :	IC1=C2N=CC(Br)=CN2N=C1
MDL No. :	MFCD18073604
InChI Key :	YYRFAUZQNJMKHU-UHFFFAOYSA-N
Pubchem ID :	56845243

Safety of [ 1109284-33-4 ]

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

Computational Chemistry of [ 1109284-33-4 ] 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	2.0
Num. H-bond donors	0.0
Molar Refractivity	53.4
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	30.19 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.98
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	1.67
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.1
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.	2.26
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	2.13
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.03

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.51
Solubility	0.101 mg/ml ; 0.000312 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.	-1.92
Solubility	3.91 mg/ml ; 0.0121 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	-3.49
Solubility	0.104 mg/ml ; 0.000322 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.	-7.09 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	1.0 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)	2.14

Application In Synthesis of [ 1109284-33-4 ]

* 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 [ 1109284-33-4 ]

[ 1109284-33-4 ] Synthesis Path-Downstream 1~25

1
[ 705263-10-1 ]
[ 1109284-33-4 ]

Yield	Reaction Conditions	Operation in experiment
	With ammonium cerium (IV) nitrate; iodine; In acetonitrile; at 20.0℃; for 24.0h;	A mixture of compound 6-bromopyrazolo[l,5-alpha]pyrimidine (1 eq), eerie ammonium nitrate (0.6 eq), and I2 (0.6 eq) in acetonitrile (10 mL) was stirred over a period of 24 h at room temperature. The formed precipitate was filtered off, washed with acetonitrile, and recrystallized from acetonitrile. The filtrate was evaporated, and the product was extracted with dichloromethane. The latter was evaporated, and the residue was recrystallized from acetonitrile to give 6-bromo-3- iodopyrazolo[l,5-alpha]pyrimidine.

References: [1]Patent: WO2009/14620,2009,A1 .Location in patent: Page/Page column 36; 24.

2
[ 1109284-33-4 ]
[ 1109284-32-3 ]
[ 1109284-34-5 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; at 90.0℃;Inert atmosphere;	6-bromo-3-iodopyrazolo[l,5-alpha]pyrimidine (1 eq) was mixed with 4-(4,4,5,5-tetramethyl- 1,3,2- dioxaborolan-2-yl)-7v"-(2,2,2-trifluoro-l-pyridin-2-ylethyl)thiophene-2-carboxamide (1 eq, step B). Dioxane (10 mL) and IM Na2CO3 (2 eq) were added. The mixture was evacuated and flushed with nitrogen under stirring, then Pd(Ph3P)4 (0.05 eq) was added in a flow of nitrogen. The temperature was brought to 90C. The reaction mixture was stirred at this temperature overnight and concentrated. The residue was poured into a 5-fold excess of water. The mixture was extracted with chloroform. The organic layer was washed with brine, dried with MgSO4, and concentrated. The residue was purified by column chromatography (dichloromethane- methanol, 100:1) to give 4-(6-bromopyrazolo[l,5-alpha]pyrimidin-3-yl)-iV-(2,2,2-trifluoro-l-pyridin- 2-ylethyl)thiophene-2-carboxamide.

References: [1]Patent: WO2009/14620,2009,A1 .Location in patent: Page/Page column 36.

3
[ 1109284-33-4 ]
4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-N-(2,2,2-trifluoroethyl)thiophene-2-carboxamide [ No CAS ]
4-(6-bromopyrazolo[1,5-a]pyrimidin-3-yl)-N-(2,2,2-trifluoroethyl)thiophene-2-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water; at 85.0℃;Inert atmosphere;	Dioxane (100 ml) and 1M sodium carbonate, Aq. solution (16.37 ml, 16.37 mmol) were added to a flask containing 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-N-(2,2,2-trifluoroethyl)thiophene-2-carboxamide (3.43 g, 10.23 mmol) and <strong>[1109284-33-4]6-bromo-3-iodopyrazolo[1,5-a]pyrimidine</strong> (3.32 g, 10.23 mmol). The mixture was flushed with nitrogen gas, after which Tetrakis(triphenylphosphine)palladium(0) (0.473 g, 0.409 mmol) was added. The temperature was increased to 85 C and the reaction mixture was allowed to stir overnight. After cooling to room temperature, the reaction mixture was mixed with water and extracted three times with chloroform. The organic layer was washed with brine, dried over magnessium sulfate, filtered, and the solvent removed in vacuo. Purified 40g silica gel cartridge, 10% DCM 70% Hexanes, 20% EtOAc. LRMS (APCI) calc?d for (C13H8BrF3N4OS) [M+H]+, 405.0; found 404. 1H NMR (600 MHz, CDCl3) delta 8.89 - 8.68 (m, 1H), 8.56 - 8.45 (m, 1H), 8.33 (s, 1H), 8.15 (t, J = 5.9, 1H), 8.06 - 7.92 (m, 1H), 6.28 (s, 1H), 4.13 (qt, J = 18.2, 36.3, 2H).