1211530-54-9|5-(Bromomethyl)nicotinonitrile| Ambeed

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Quality Control of [ 1211530-54-9 ] Purity: 97% SDS Specification

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Product Details of [ 1211530-54-9 ]

CAS No. :	1211530-54-9
Formula :	C₇H₅BrN₂
M.W :	197.03
SMILES Code :	N#CC1=CN=CC(CBr)=C1
MDL No. :	MFCD18262164
InChI Key :	IUHPOQYVQPBUBT-UHFFFAOYSA-N
Pubchem ID :	57475499

Safety of [ 1211530-54-9 ]

GHS Pictogram:
Signal Word:	Danger
Hazard Statements:	H302-H314
Precautionary Statements:	P260-P264-P270-P280-P301+P330+P331-P303+P361+P353-P304+P340-P305+P351+P338-P310-P363-P405-P501
Class:	8
UN#:	3261
Packing Group:	Ⅱ

Computational Chemistry of [ 1211530-54-9 ] Show Less

Physicochemical Properties

Num. heavy atoms	10
Num. arom. heavy atoms	6
Fraction Csp3	0.14
Num. rotatable bonds	1
Num. H-bond acceptors	2.0
Num. H-bond donors	0.0
Molar Refractivity	41.79
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	36.68 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.56
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	1.13
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.7
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.	0.62
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	2.31
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.46

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.15
Solubility	1.39 mg/ml ; 0.00706 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.	-1.49
Solubility	6.32 mg/ml ; 0.0321 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	-3.37
Solubility	0.0837 mg/ml ; 0.000425 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.	-6.7 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	1.0
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<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)	2.01

Application In Synthesis of [ 1211530-54-9 ]

* 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 [ 1211530-54-9 ]

[ 1211530-54-9 ] Synthesis Path-Downstream 1~16

1
[ 1211530-54-9 ]
[ 1263413-29-1 ]
[ 1263411-55-7 ]
[ 1263411-57-9 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate;potassium iodide; In N,N-dimethyl-formamide; at 20℃;	Racemic 8-bromo-2,2-difluoro-2H-1 ,4-benzoxazin-3(4H)-one (50 mg, 0.189 mmol, intermediate 4), <strong>[1211530-54-9]5-(bromomethyl)-3-pyridinecarbonitrile</strong> (37.3 mg, 0.189 mmol, intermediate 24), potassium carbonate (52.3 mg, 0.379 mmol) and potassium iodide (0.314 mg, 1.894 mumol) were dissolved in DMF (3000 mul) in a 10 ml. round-bottomed flask open to the atmosphere and stirred at room temperature overnight. The reaction mixture was evaporated to dryness, redissolved in EtOAc (30ml) and treated with saturated aqueous sodium bicarbonate (30ml). The aqueous layer was extracted with EtOAc (2x30ml) and the organic layers were combined, washed with brine (30ml), dried over magnesium sulfate, filtered and evaporated to dryness to give the crude product (119mg) as a light brown oil. The crude product was purified on a 25+S Biotage silica cartridge, eluting with a 0 to 70% mixture of EtOAc in hexane. This gave an off-white solid (54 mg). 47 mg of this racemic mixture was resolved using a Chiralpak AS column eluting with heptane: ethanol (90:10) v/v pump-mixed. Using these conditions the faster- running enantiomer (20 mg, Compound 57 or 58) and the slower-running enantiomer (15 mg, Compound 57 or 58) were obtained in >99% enantiomeric excess. 1H NMR (CD3OD) delta: 1.45 (3H, d), 5.23 (1 H, q), 5.41 (2H, s), 7.18 (1 H, dd), 7.25 (1 H, t), 7.42 (1 H, dd), 8.14 (1 H, s), 8.78 (1 H, d), 8.84 (1 H, d). m/z [M+H]+: 345.9. Retention time 0.81 min (LC/MS method 3).

References: [1]Patent: WO2011/12622,2011,A1 .Location in patent: Page/Page column 139; 140.

2
[ 1211530-54-9 ]
[ 1263413-30-4 ]
[ 1263411-55-7 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate;potassium iodide; In N,N-dimethyl-formamide; at 20℃;	2,2-Difluoro-8-[(1S)-1-hydroxyethyl]-2H-1 ,4-benzoxazin-3(4H)-one (75 mg, may be prepared as described in intermediate 5), <strong>[1211530-54-9]5-(bromomethyl)-3-pyridinecarbonitrile</strong> (233 mg, may be prepared as described in intermediate 24), potassium carbonate (90 mg, 0.655 mmol) and potassium iodide (0.543 mg, 3.27 mumol) were dissolved in DMF (5000 mul) in a 25 ml. round-bottomed flask open to the atmosphere and stirred at room temperature overnight. The reaction mixture was evaporated to dryness, redissolved in EtOAc (30ml) and treated with saturated aqueous sodium bicarbonate (30ml). The aqueous layer was extracted with EtOAc (2x30ml) and the organic layers were combined, washed with brine (30ml), dried over magnesium sulfate, filtered and evaporated to dryness to give the crude product (194mg) as a light brown oil. The crude product was purified on a 25+S Biotage silica cartridge, eluting with a 0 to 75 % mixture of EtOAc in hexane. The title compound was obtained (87 mg) as an cream solid. 1H NMR (DMSO-de) delta: 1.34 (3H, d), 5.02 - 5.10 (1 H, m), 5.36 - 5.42 (3H, m), 7.21 - 7.25 (2H, m), 7.37 (1 H, dd), 8.32 (1 H, s), 8.87 (1 H, d), 8.95 (1 H, d). m/z [M+H]+: 346.2. Retention time 0.84 min (LC/MS method 3).

References: [1]Patent: WO2011/12622,2011,A1 .Location in patent: Page/Page column 140.

3
[ 1211530-54-9 ]
4-((3-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-2-methylbenzyl)oxy)-2-hydroxybenzaldehyde [ No CAS ]
2-((5-(3-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-2-methylbenzyloxy)-2-formylphenoxy)methyl)isonicotinonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
13.8%	With caesium carbonate; In N,N-dimethyl-formamide; at 75℃;	Cesium carbonate (173 mg, 0.531 mmol), 4-((3-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-2-methylbenzyl)oxy)-2-hydroxy-6-methylbenzaldehyde (100 mg, 0.256 mmol) and 3-(bromomethyl)benzonitrile (81 mg, 0.531 mmol) were stirred in dimethyl formamide at 75 C. overnight. The mixture was diluted with ethyl acetate, neutralized with dilute hydrochloric acid (0.1 N) and washed with water and brine. Dried over sodium sulfate. Filtered and removed the solvent by rotary evaporation. The residue was purified with 2:3 hexanes:ethyl acetate on a 24 g silica gel column. Collected fractions to afford a white solid (18 mg, 13.8% yield).

References: [1]Patent: US2015/291549,2015,A1 .Location in patent: Paragraph 0409; 0410.

4
[ 1211530-54-9 ]
(3-((2-(((1R,3s,5S)-9-azabicyclo[3.3.1]nonan-3-yl)(methyl)amino)-6-methoxypyrimidin-4-yl)amino)-1H-pyrazol-5-yl)methanol hydrochloride [ No CAS ]
[ 76-05-1 ]
5-(((1R,3s,5S)-3-((4-((5-(hydroxymethyl)-1H-pyrazol-3-yl)amino)-6-methoxypyrimidin-2-yl)(methyl)amino)-9-azabicyclo[3.3.1]nonan-9-yl)methyl)nicotinonitrile trifluoroacetic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
3.7 mg		A solution of (3-((2-(((1R,3s,5S)-9-azabicyclo[3.3.1]nonan-3-yl)(methyl)amino)-6-methoxypyrimidin-4-yl)amino)-1H-pyrazol-5-yl)methanol HCl (20 mg, 0.054 mmol), <strong>[1211530-54-9]5-(bromomethyl)nicotinonitrile</strong> (10.55 mg, 0.054 mmol) and potassium carbonate (22.20 mg, 0.161 mmol) were stirred in DMF (6.0 mL) at 60 C. overnight. The reaction mixture was concentrated in vacuo and purified by reverse-phase HPLC to provide the TFA salt of the title intermediate (3.7 mg). (m/z): [M+H]+ calcd for C25H31N9O2 490.26 found 490.2.

References: [1]Patent: US2017/312280,2017,A1 .Location in patent: Paragraph 0304; 0305.

5
[ 1211530-54-9 ]
5-chloro-2-hydroxy-4-(4-phenylindan-1-yl)oxybenzaldehyde [ No CAS ]
5-[[4-chloro-2-formyl-5-(4-phenylindan-1-yl)oxyphenoxy]methyl]pyridine-3-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate; In N,N-dimethyl-formamide; at 65℃; for 2.0h;	To a solution of 5-chloro-2-hydroxy-4-(4-phenylindan-1-yl)oxy-benzaldehyde (100 mg, 0.274 mmol) in DMF (5 mL) was added <strong>[1211530-54-9]5-(bromomethyl)pyridine-3-carbonitrile</strong> (108 mg, 0.549 mmol) followed by Cs2CO3 (178 mg, 0.549 mmol). The resulting suspension was then stirred at 65 C. for 2 h. The reaction mixture was diluted with EtOAc (20 mL),washed with water (20 mL), dried (MgSO4), concentrated in vacuo. The crude residue was purified by flash chromatography (SiO2, 80% EtOAc in hexanes) to obtain 5-[[4-chloro-2-formyl-5-(4-phenylindan-1-yl)oxy-phenoxy]methyl]pyridine-3-carbonitrile. MS: (ES) m/z calculated for C29H22ClN2O3[M+H]+ 481.1. found 481.3.

References: [1]Patent: US2018/8554,2018,A1 .Location in patent: Paragraph 0192; 0195.

6
[ 1211530-54-9 ]
4-[(1R)-4-bromoindan-1-yl]oxy-5-chloro-2-hydroxybenzaldehyde [ No CAS ]
5-[[5-[(1R)-4-bromoindan-1-yl]oxy-4-chloro-2-formylphenoxy]methyl]pyridine-3-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate; In N,N-dimethyl-formamide; at 20℃;	To a solution of 4-[(1R)-4-bromoindan-1-yl]oxy-5-chloro-2-hydroxy-benzaldehyde (0.84 g, 2.29 mmol) in DMF (12 mL) was added <strong>[1211530-54-9]5-(bromomethyl)nicotinonitrile</strong> (0.54 g, 2.75 mmol), followed by Cs2CO3 (1.5 g, 4.58 mmol). After stirring at room temperature overnight, the reaction mixture was diluted with 2:1 CHCl3/i-PrOH (30 mL) and washed with water (20 mL). The aqueous layer was re-extracted with 2:1 CHCl3/i-PrOH (2*15 mL). The combined organic layers were dried (MgSO4), filtered, and concentrated in vacuo. The crude was suspended in 1:1 CH2Cl2/hexanes (10 mL) and filtered to obtain 5-[[5-[(1R)-4-bromoindan-1-yl]oxy-4-chloro-2-formyl-phenoxy]methyl]pyridine-3-carbonitrile. MS: (ES) m/z calculated for C23H16BrClN2O3[M+H]+ 483.0. found 483.2.

References: [1]Patent: US2018/8554,2018,A1 .Location in patent: Paragraph 0301; 0305.

7
[ 1211530-54-9 ]
5-[[4-chloro-2-[[(2-hydroxy-2-methyl-propyl)amino]methyl]-5-[(1S)-4-phenylindan-1-yl]oxyphenoxy]methyl]pyridine-3-carbonitrile [ No CAS ]