1191616-45-1|4-(4-Bromophenyl)-1-methyl-1H-pyrazole| Ambeed

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Quality Control of [ 1191616-45-1 ] Purity: 97% SDS Specification

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Product Details of [ 1191616-45-1 ]

CAS No. :	1191616-45-1
Formula :	C₁₀H₉BrN₂
M.W :	237.10
SMILES Code :	CN1N=CC(C2=CC=C(Br)C=C2)=C1
MDL No. :	MFCD19322918
InChI Key :	NGFPKROKTIBKMD-UHFFFAOYSA-N
Pubchem ID :	66861254

Safety of [ 1191616-45-1 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H317
Precautionary Statements:	P280

Computational Chemistry of [ 1191616-45-1 ] Show Less

Physicochemical Properties

Num. heavy atoms	13
Num. arom. heavy atoms	11
Fraction Csp3	0.1
Num. rotatable bonds	1
Num. H-bond acceptors	1.0
Num. H-bond donors	0.0
Molar Refractivity	56.63
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	17.82 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.32
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	2.55
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.85
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.	2.47
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	2.65
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.57

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.48
Solubility	0.0791 mg/ml ; 0.000334 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.	-2.57
Solubility	0.636 mg/ml ; 0.00268 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	-4.17
Solubility	0.0159 mg/ml ; 0.0000671 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Moderately 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	Yes
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.	-5.94 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<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)	1.74

Application In Synthesis of [ 1191616-45-1 ]

* 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 [ 1191616-45-1 ]

[ 1191616-45-1 ] Synthesis Path-Downstream 1~27

1
[ 39806-90-1 ]
[ 5467-74-3 ]
[ 1191616-45-1 ]

Yield	Reaction Conditions	Operation in experiment
76%	With tetrakis(triphenylphosphine) palladium(0); caesium carbonate; In 1,2-dimethoxyethane; water; at 90℃; for 0.116667h;Microwave irradiation; Inert atmosphere;	General procedure: 4-Iodo-1-methyl-1H-pyrazole 1 (101 mg, 0.5 mmol) and phenylboronic 2 (59 mg, 0.5 mmol) were dissolved in DME (3 mL) and H2O (1.2 mL) in a microwave vial under a nitrogen atmosphere. Pd(PPh3)4 (2 mmol%, 11.6 mg) and Cs2CO3 (407.3 mg, 1.25 mmol) were added, and the reaction mixture was irradiated in a microwave apparatus at 90 C for 5-12 min. After the reaction mixture was cooled to ambient temperature, the product was concentrated, and the crude mixture was purified by silica gel column chromatography using petroleum ether/acetone as eluent to give the title compound.

References: [1]Chinese Chemical Letters,2014,vol. 25,p. 705 - 709.

2
[ 1191616-45-1 ]
[ 73183-34-3 ]
[ 1607838-14-1 ]

Yield	Reaction Conditions	Operation in experiment
85%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate; In N,N-dimethyl-formamide; acetonitrile; at 80℃; for 18h;Inert atmosphere;	Potassium acetate (199 mg, 2.0 mmol), bis(pinacolato)diboron (257 mg, 1.0 mmol) and <strong>[1191616-45-1]4-(4-bromophenyl)-1-methyl-pyrazole</strong> (160 mg, 0.67 mmol) were mixed in DMF (1 mL) and MeCN (4 mL) and the mixture degassed with N2. [1,1'-Bis(diphenylphosphino)ferrocene]Palladium(II) chloride dichloromethane complex (55 mg, 0.07 mmol) was added and the mixture heated for 18 h at 80 C. The reaction mixture was concentrated and purified by silica column chromatography, eluting with 5-20% EtOAc in Pet. Ether to afford 1-methyl-4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-15 yl)phenyl]pyrazole (163 mg, 0.57 mmol, 85% yield) as a white solid. LC-MS (ES+, Method A): 1.79 min, m/z 285.0 [M+H]+
73%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate; In N,N-dimethyl-formamide; acetonitrile; at 120℃; for 0.5h;Inert atmosphere; Microwave irradiation;	A solution of 4-(4-bromophenyl)-l -methyl- lH-pyrazole (0.33 g, 1.18 mmol), bis(pinacolato)diboron (0.36 g, 1.42 mmol) and potassium acetate (0.35 g, 3.55 mmol) in DMF (3.5 mL) and CH3CN (7 mL) was stirred and degassed with nitrogen for 10 minutes. Ferrocene] palladium (II) dichloromethane adduct (CAS number 95464-05-4) (0.097 g, 0.12 mmol) was added and the resulting mixture was heated at 120C using a monomode microwave (Biotage initiator 60) with a power output ranging from 0 to 400 W for 30 minutes. The mixture was evaporated till dryness, the residue was taken up in CH2CI2 and water, filtered through a short pad of Celite. The organic layer of the filtrate was separated, washed with water, dried over MgS04 and evaporated till dryness. The purification was carried out by flash chromatography over silica gel (15-40muiotaeta, 40 g, heptane/EtOAc from 95/5 to 70/30). The pure fractions were collected and the solvent was evaporated to afford 0.024g (73%) of intermediate (14).

References: [1]Patent: WO2019/145729,2019,A1 .Location in patent: Page/Page column 261.
[2]Patent: WO2015/14836,2015,A1 .Location in patent: Page/Page column 19.
[3]Patent: WO2019/238067,2019,A1 .Location in patent: Paragraph 0401; 0490-0492.

3
[ 106-37-6 ]
[ 761446-44-0 ]
[ 1191616-45-1 ]

Yield	Reaction Conditions	Operation in experiment
75%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,4-dioxane; water; at 80℃; for 3h;Inert atmosphere;	Into a 250-mL round-bottom flask purged and maintained with an inert atmosphere of nitrogen was placed 1-methyl-4-(tetramethyl-1 ,3,2- dioxaborolan-2-yl)-1 H-pyrazole (2.00 g, 9.61 mmol), 1 ,4-dibromobenzene (2.30 g, 9.75 mmol), Pd(PPh3)4 (550 mg, 0.48 mmol), potassium carbonate (2.60 g, 18.8 mmol), dioxane (40 ml_) and water (10 ml_). The resulting solution was stirred for 3 h at 80C. The resulting mixture was evaporated to dryness. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1/10). This resulted in 1.70 g (75%) of 4-(4- bromophenyl)-1-methyl-1 H-pyrazole as a yellow solid.
47%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,4-dioxane; water; at 80℃; for 18h;Inert atmosphere; Sealed tube;	1-methylpyrazole-4-boronic acid pinacol ester (300 mg, 1.44 mmol) 1,4-dibromobenzene (0.2 mL, 1.6 mmol) and potassium carbonate (399 mg, 20 2.9 mmol) were mixed in water (1 mL) and 1,4-dioxane (4 mL) and the mixture degassed with N2. tetrakis(triphenylphosphine)palladium(0) (167 mg, 0.14 mmol) was added and the tube sealed and heated at 80 C for 18h. The reaction mixture was reduced in vacuo directly onto silica and purified by silica column chromatography, eluting with 5-40% EtOAc in Pet. Ether to afford 4-(4-bromophenyl)-1-methyl-pyrazole (160 mg, 0.67 mmol, 47% yield) as a white solid. LC-MS (ES+, 25 Method A): 1.66 min, m/z 237.1 [M+H]+.

References: [1]Patent: WO2016/41618,2016,A1 .Location in patent: Page/Page column 69.
[2]Patent: WO2019/145729,2019,A1 .Location in patent: Page/Page column 261.

4
[ 1191616-45-1 ]
{3-[4-(1-methyl-1H-pyrazol-4-yl)benzyl]-1H-indazol-5-yl}pyridin-4-yl-amine [ No CAS ]