426219-35-4|6-Bromo-N-methyl-2-naphthamide| Ambeed

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Quality Control of [ 426219-35-4 ] Purity: 95% SDS Specification

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Product Details of [ 426219-35-4 ]

CAS No. :	426219-35-4
Formula :	C₁₂H₁₀BrNO
M.W :	264.12
SMILES Code :	O=C(NC)C1=CC=C2C=C(Br)C=CC2=C1
MDL No. :	MFCD14708203
InChI Key :	HPUCFMPIKISIIO-UHFFFAOYSA-N
Pubchem ID :	21879628

Safety of [ 426219-35-4 ]

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

Computational Chemistry of [ 426219-35-4 ] Show Less

Physicochemical Properties

Num. heavy atoms	15
Num. arom. heavy atoms	10
Fraction Csp3	0.08
Num. rotatable bonds	2
Num. H-bond acceptors	1.0
Num. H-bond donors	1.0
Molar Refractivity	64.64
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	29.1 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.34
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	3.14
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.96
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.	3.18
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	3.18
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.96

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.82
Solubility	0.0402 mg/ml ; 0.000152 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.	-3.42
Solubility	0.1 mg/ml ; 0.00038 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	-5.32
Solubility	0.00128 mg/ml ; 0.00000484 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.	-5.68 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)	1.06

Application In Synthesis of [ 426219-35-4 ]

* 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 [ 426219-35-4 ]

[ 426219-35-4 ] Synthesis Path-Downstream 1~35

1
aqueous ammonium chloride [ No CAS ]
n-butyllithium hexane [ No CAS ]
[ 426219-35-4 ]
[ 426219-43-4 ]
[ 426219-18-3 ]

Yield	Reaction Conditions	Operation in experiment
	With ammonia; In tetrahydrofuran;	Example 5 Production of 6-(7-hydroxy-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-7-yl)-N-methyl-2-naphthamide Dry THF (150 ml) was cooled to -65 C. in a dry ice-acetone bath under an argon atmosphere and n-butyl lithium hexane solution (1.6M: 45.2 ml) was added. A solution of <strong>[426219-35-4]6-bromo-N-methyl-2-naphthamide</strong> (8.68 g) in dry THF (700 ml) cooled to 10 C. was added to this solution at not more than -55 C., and the mixture was stirred for 1 h. A dry THF solution (60 ml) of 5,6-dihydro-7H-pyrrolo[1,2-c]imidazol-7-one (3.65 g) was added dropwise. The mixture was stirred at the same temperature for 1.5 h and saturated aqueous ammonium chloride solution (120 ml) was added to stop the reaction. The solvent was evaporated under reduced pressure and an ethanol-soluble material was extracted from the resulting residue and the solvent was evaporated again. The residue was purified by flash silica gel column chromatography (eluent, chloroform/methanol containing ammonia (7%), 19/1?9/1). The elude was recrystallized from methanol to give the title compound (3.36 g) as colorless crystals. 1H-NMR(CDCl3+CD3OD) delta: 2.89-3.02(2H, m), 3.04(3H, s), 4.124.25(1H, m), 4.27-4.43(1H, m), 6.79(1H, s), 7.20(1H, q, J=4.6 Hz), 7.54(1H, s), 7.63(1H, dd, J=1.8 Hz, 8.6 Hz), 7.83(2H, s), 7.89(1H, d, J=8.6 Hz), 8.03(1H, s), 8.28(1H, s). IR(KBr):3500-3000, 1644, 1605, 1559, 1497, 1464, 1318, 1082 cm-1.

References: [1]Patent: US2004/33935,2004,A1 .

2
aqueous ammonium chloride [ No CAS ]
n-butyllithium hexane [ No CAS ]
[ 426219-35-4 ]
[ 392-83-6 ]
[ 426219-43-4 ]
[ 426219-18-3 ]

Yield	Reaction Conditions	Operation in experiment
	With ammonia; In tetrahydrofuran;	Example 10 Production of 6-(7-hydroxy-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-7-yl)-N-methyl-2-naphthamide Under an argon atmosphere, 2-bromobenzotrifluoride (33.05 g) was dissolved in dry THF (600 ml), and the mixture was cooled to -65 C. in a dry ice-acetone bath. An n-butyl lithium hexane solution (1.6M: 93.7 ml) was added with stirring and the mixture was stirred at the same temperature for 30 min. After stirring the mixture, a dry THF (2.88L) solution of <strong>[426219-35-4]6-bromo-N-methyl-2-naphthamide</strong> (38.03 g) cooled to 10 C. was added at not more than -55 C. The mixture was stirred for 20 min. An n-butyl lithium hexane solution (1.6M: 94.5 ml) was added at not more than -65 C. The mixture was stirred for 30 min and 5,6-dihydro-7H-pyrrolo[1,2-c]imidazol-7-one (14.66 g) in a dry THF solution (240 ml) was added dropwise. The mixture was stirred at the same temperature for 1.5 h and saturated aqueous ammonium chloride solution (520 ml) was added to stop the reaction. The solvent was evaporated under reduced pressure and an ethanol-soluble material was extracted from the resulting residue and the solvent was evaporated again. The resulting residue was purified by flash silica gel column chromatography (eluent; chloroform/methanol containing ammonia (7%); 19/1?9/1). The elude was recrystallized from methanol to give the title compound (16.44 g) as colorless crystals. The physical and chemical data were identical with those of the compound obtained in Example 5.

References: [1]Patent: US2004/33935,2004,A1 .

3
[ 426219-35-4 ]
[ 33016-47-6 ]
[ 566200-96-2 ]

Yield	Reaction Conditions	Operation in experiment
74%		Example 1Under a nitrogen atmosphere, 6-bromo-N-methyl-2- naphthamide (7.0 g, 26.5 mmol) was added to tetrahydrofuran (175 mL) , and then 2.0 mol/L isopropylmagnesium chloridetetrahydrofuran solution (13.7 mL) was added dropwise thereto at room temperature. The reaction mixture was cooled to -30C, 1.6 mol/L n-butyllithium hexane solution (26.6 mL) was added dropwise thereto, and the mixture, was stirred at the same temperature for 2 hr. To the reaction mixture was addeddropwise a solution of l-trityl-4-formyl-lH-imidazole (13.5 g, 39.9 mmol) in tetrahydrofuran (140 mL) at -20C, and themixture was stirred at the same temperature for 2 hr. The reaction mixture was allowed to warm to 0C, and stirred for 1 hr, and 20w/v% aqueous ammonium chloride solution (105 mL) was added dropwise thereto. The organic layer was separated, and concentrated to the volume of about 90 mL under reducedpressure. To the residue was added tetrahydrofuran (140 mL) , and the mixture was concentrated to the volume of about 90 mL under reduced pressure. To the residue was added acetone (140 mL) , and the mixture was concentrated to the volume of about 140 mL under reduced pressure. These operations were repeated three times. To the residue was added acetone to adjust the volume to about 180 mL, and the mixture was stirred at room temperature. The crystals were collected by filtration, and washed with acetone (70 mL) . The obtained wet crystals were dried under reduced pressure to give 6- [hydroxy ( 1-trityl-lH- imidazol-4-yl) methyl] -N-methyl-2-naphthamide (10.3 g, 19.7 mmol) . yield 74%.½ NMR (500 MHz , DMSO-d6) delta 2.84 (d, J = 4.7 Hz, 3H) , 5.76 (d, J = 5.0 Hz, 1H), 5.82 (d, J = 4.7 Hz, 1H) , 6.80 (s, 1H) , 6.98- 7.13 (m, 6H) , 7.28 (d, J = 1.6 Hz, 1H) , 7.32-7.50 (m, 9H) , 7.55 (dd, J = 8.5, 1.6. Hz, 1H) , 7.83-7.99 (m,. 4H) 8.37 (s, 1H) 8.58 (d, J = 4.4 Hz, 1H) ; HRMS (ESI) m/z Calcd for aC35H30 3O2 [M+H] +: 524.2338, Found: 524.2325; Anal. Calcd for a C35H29 3O2: C, 80.28; H, 5.58; N, 8.02. Found: C, 80.17; H, 5.80; N, 7.81.[0097]
71%		Example 2Under a nitrogen atmosphere, 6-bromo-N-methyl-2- naphthamide (1.0 g, 3.79 mmol) was added to tetrahydrofuran (25 mL) , and then 1.0 mol/L dibutylmagnesium heptane solution (2.0 mL) was added dropwise thereto at room temperature. The obtained solution was cooled to -13C, 1.6 mol/L n-butyllithium hexane solution (2.6 mL) was added dropwise thereto, and the mixture was. stirred at the same temperature for 1.5 hr. A solution of l-trityl-4-formyl-lH-imidazole (1.4 g, 4.2 mmol) in tetrahydrofuran (15 mL) was added dropwise to the reaction mixture at -11C, and the mixture was stirred at the same temperature for 5 hr. The reaction mixture was allowed to warm to 6C over 2.5 hr, and 20w/v% aqueous ammonium chloride solution (30 mL) was added dropwise thereto. The organic layer was separated, and quantified to give 6- [hydroxy (1-trityl-lH- imidazol-4-yl) methyl] -N-methyl-2-naphthamide (1.2 g, 2.24 mmol). yield 71%.
58%		Reference Example 8Under a nitrogen atmosphere, o- bromotrifluoromethylbenzene (1.35 kg, 6.00 mol) was added to tetrahydrofuran (7.9 L) . The reaction mixture was cooled to - 70C, 1.6 mol/L n-butyllithium hexane solution (3.75 L, 6.00 mol) was. added dropwise thereto, and the mixture was stirred at the same temperature for about 30 min. The reaction mixture was added dropwise at the same temperature to a solution prepared by adding <strong>[426219-35-4]6-bromo-N-methyl-2-naphthamide</strong> (1.13 kg, 4.28 mol) to THF (62.2 L) at -70C under a nitrogen atmosphere, and the mixture was stirred for 1.5 hr. To the reactionmixture were added dropwise successively 1.6 mol/L n- butyllithium hexane solution (2.67 L, 4.27 mol) and a solution of l-trityl-4-formyl-lH-imidazole (1.21 kg, 3.58 mol) in THF (7.9 L) at the same temperature, and the mixture was stirred for 2 hr. The reaction mixture was allowed to warm to -10C, and 20w/v% aqueous ammonium chloride solution (17.0 L) was added dropwise thereto at -10 to 0C. The separated organic layer was concentrated under reduced pressure. To the residue was added ethyl acetate . (11.3 L) , and the mixture was stirred at room temperature. The crystals were collected by filtration, and washed with ethyl acetate (11.3 L) . The obtained wet crystals were dried under reduced pressure to give 6- [hydroxy ( l-trityl-lH-imidazol-4-yl) methyl] -N-methyl-2- naphthamide (1.31 kg, 2.50 mol). yield 58%.

50%

Under nitrogen atmosphere, 5.8 liters of THF was added to 105.6 g (0.40 mol, 1.2eq) of 6-bromo-N-methyl-2-naphtamide, the mixture was warmed to 50C to dissolve it. 500 ML (0.50 mol, 2.4eq) of a 1.6 M solution of n-butyllithium in hexane was added dropwise at -65C or lower over 35 minutes.. The mixture was stirred at -65C for 1 hour.. A solution of 112.7 g (0.33 mol) of 1-trityl-4-formyl-1H-imidazole in 810 ML of THF was added dropwise at -65C or lower over 40 minutes.. The mixture was stirred at -65C for 2 hours. 1.5 Liters of an aqueous saturated ammonium chloride solution was added dropwise at -20C or lower, and the mixture was warmed to 30C. After separation of the layers, the organic layer was washed with 1.5 liters of an aqueous saturated sodium chloride solution two times.. After concentration under reduced pressure, 1 liter of ethyl acetate was added to the residue, and the mixture was stirred at 25C for 3 hours.. Crystals were filtered, and washed with ethyl acetate.. Vacuum drying (50C) to a constant weight afforded 87.9 g of 6-[hydroxy(1-trityl-1H-imidazol-4-yl)methyl]-N-methyl-2-naphthamide (yield 50%).1H NMR (DMSO-d6): delta 2.82 (3H, d, J=4.4 Hz), 5.76 (2H, q,J=6.6 Hz), 6.78 (1H, s), 7.06-7.09 (6H, m), 7.26 (1H, s), 7.33-7.42 (9H, m), 7.53 (1H, d, J=8.5 Hz) 7.88-7.93 (4H, m) 8.36 (1H, s), 8.55 (1H, d, J=4.5 Hz).

References: [1]Patent: WO2012/173280,2012,A1 .Location in patent: Page/Page column 36-37.
[2]Patent: WO2012/173280,2012,A1 .Location in patent: Page/Page column 37.
[3]Patent: WO2012/173280,2012,A1 .Location in patent: Page/Page column 33-34.
[4]Patent: EP1471056,2004,A1 .Location in patent: Page 32.

4
[ 5773-80-8 ]
[ 74-89-5 ]
[ 426219-35-4 ]

Yield	Reaction Conditions	Operation in experiment
89%		Reference Example 76-Bromo-2-naphthoic acid (10.1 g, 40.1 mmol) and N,N- dimethylformamide (4.75 g, 65.0 mmol) were added to toluene (80 mL) . To the reaction mixture was added dropwise thionyl chloride (5.7 g, 48.2 mmol) at 45 to 50C, and the mixture was stirred for 1 hr, and allowed to cool to room temperature. The reaction mixture was added dropwise at 10 to 25C to a solution prepared by adding triethylamine (11.4 g, 112.4 mmol) and 40% methylamine methanol solution (8.1 g, 104.4 mmol) to toluene (80 rnL) , and the mixture was stirred at room temperature for 1 hr.. To the reaction mixture was added dropwise water (50 mL) , and the mixture was stirred at room temperature. The crystals were collected by filtration, and washed with a mixed solvent (25 mL) of methanol/water (2:8) to give wet crystals. The total amount of the wet crystals was added to N,N- dimethylacetamide (70 mL) , and dissolved with heating to 60C. The reaction mixture was allowed to cool to room temperature, and water (140 mL) was added dropwise thereto. The crystals were collected by filtration, and washed with water (80 mL) to give wet crystals. The total amount of the wet crystals was suspended in ethyl acetate -(25 mL) with stirring at roomtemperature. The crystals were collected by filtration, and washed with ethyl acetate (5 mL) . The obtained wet crystals were dried under reduced pressure to give 6-bromo-N-methyl-2- naphthamide (9.4 g, 35.6 mmol). yield 89%.¾ NMR (500 MHz, DMSO-d6) delta 2.84 (d, J = 4.4 Hz, 3H) , 7.71 (dd, J = 8.8, 2.2 Hz, 1H) , 7.93 - 8.03 (m, 3H) , 8.28 (d, J = 1.9 Hz, 1H), 8.44 (s, 1H) , 8.62 (d, J = 4.1 Hz, 1H) ; HRMS (ESI) m/z Calcd for a Ci2HuNOBr [M+H]+: 264.0024, Found: 264.0019; Anal. Calcd for a Ci2Hi0NOBr: C, 54.57; H, 3.82; N, 5.30; Br, 30.25. Found: C, 54.56; H, 3.70; N, 5.34; Br, 30.23.
82%	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; N,N-dimethyl-formamide; at 0 - 20℃; for 18h;Inert atmosphere;	Under an argon atmosphere, to a cooled (0 C) solution of 8 (60.26 g, 240 mmol), EDCI·HCl (55.21 g, 288 mmol), HOBt·H2O (44.1 g, 288 mmol) and N,N-diisopropylethylamine ((i-Pr)2NEt) (37.23 g, 288 mmol) in anhydrous N,N-dimethylformamide (DMF) (960 mL) was added dropwise to a solution of MeNH2 (2 M solution in THF; 192 mL, 384 mmol) and the whole was stirred at room temperature for 18 h. After dilution with water, the precipitate was filtered off, washed with H2O and i-Pr2O and dried under the reduced pressure to give 9a (60.6 g, 82%) as a colorless powder. 1H NMR (CDCl3 + CD3OD) delta: 3.04 (3H, s), 7.60 (1H, dd, J = 1.8 Hz, 8.6 Hz), 7.78 (2H, d, J = 8.6 Hz), 7.85 (1H, dd, J = 1.8 Hz, 8.6 Hz), 8.03 (1H, d, J = 1.8 Hz), 8.25 (1H, s). IR (KBr): 3274, 1638, 1622, 1559, 1495, 1408, 1316, 1159 cm-1. Anal. Calcd for C12H10NOBr.0.1H2O: C, 54.20; H, 3.87; N, 5.27; Br, 30.25. Found: C, 54.03; H, 3.72; N, 5.24.
80%		4 Liters of ethyl acetate and 25 ML of DMF were added to 500 g (1.99 mol) of 6-bromo-2-naphthoic acid. 188 ML (2.61 mol, 1.3eq) of thionyl chloride was added dropwise at 30C or lower.. The mixture was stirred at 65C for 30 minutes.. After cooled to 25C, a mixture of 408 ML (3.93 mol, 2eq) of a 40% solution of methylamine in methanol and 558 ML (4.01 mol, 2eq) of triethylamine was added dropwise at 25C or lower.. The mixture was stirred at 25C for 3 hours. 2.5 Liters of water was added dropwise at 25C or lower.. Crystals were filtered, and washed successively with 1.25 liters of a mixed solution of methanol/water=1/4.. Vacuum drying (50C) to a constant weight afforded 422 g of 6-bromo-N-methyl-2-naphthamide (yield 80%).1H NMR (CDCl3+CD3OD): delta 3.04 (3H, s), 7.60 (1H, dd, J=8.6, 1.8 Hz), 7.78 (2H, d, J=8.6 Hz), 7.85 (1H, dd, J=8.6, 1.8 Hz), 8.03 (1H, d, J=1.8 Hz), 8.25 (1H, s).

References: [1]Patent: WO2012/173280,2012,A1 .Location in patent: Page/Page column 32-33.
[2]Bioorganic and Medicinal Chemistry,2011,vol. 19,p. 6356 - 6374.
[3]Patent: EP1471056,2004,A1 .Location in patent: Page 32.

5
[ 426219-35-4 ]
[ 426219-44-5 ]

References: [1]Bioorganic and Medicinal Chemistry,2011,vol. 19,p. 6356 - 6374.

6
[ 426219-35-4 ]
[ 566939-85-3 ]

References: [1]Bioorganic and Medicinal Chemistry,2011,vol. 19,p. 6356 - 6374.
[2]Patent: WO2012/173280,2012,A1 .
[3]Patent: WO2012/173280,2012,A1 .
[4]Patent: WO2012/173280,2012,A1 .

7
[ 426219-35-4 ]
[ 566939-85-3 ]
[ 752243-39-3 ]

References: [1]Bioorganic and Medicinal Chemistry,2011,vol. 19,p. 6356 - 6374.

8
[ 426219-35-4 ]
2C₁₀H₁₁NO₅*C₁₈H₁₇N₃O₂ [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,2011,vol. 19,p. 6356 - 6374.

9
[ 20970-50-7 ]
[ 426219-35-4 ]
[ 1346155-91-6 ]

Yield	Reaction Conditions	Operation in experiment
38%		General procedure: nder an argon atmosphere, 9a (436 mg, 1.65 mmol) was dissolved in dry THF (30 mL) and the mixture was cooled to -65 C in a dry ice acetone bath. A n-BuLi hexane solution (1.6 M: 2.28 mL, 3.63 mmol) was added with stirring and the mixture was stirred at the same temperature for 1.5 h. After stirring, a solution of 6 (183 mg, 1.5 mmol) in dry THF (3 mL) was added dropwise and the whole was stirred at the same temperature for 1.5 h. After dilution with saturated aqueous ammonium chloride solution, the mixture was concentrated under reduced pressure. The resulting residue was dissolved in ethanol and the insoluble material was filtered off. The filtrate was concentrated under reduced pressure and the resulting residue was chromatographed on silica gel (CHCl3/7% ammonia in MeOH = 19:1) and crystallized from CHCl3 and diethylether to give 3c (121 mg, 26%) as a colorless powder.

References: [1]Bioorganic and Medicinal Chemistry,2011,vol. 19,p. 6356 - 6374.

10
[ 426219-35-4 ]
[ 426219-43-4 ]
[ 426219-18-3 ]

Yield	Reaction Conditions	Operation in experiment
45%		Under an argon atmosphere, 2-bromobenzotrifluoride (33.05 g, 147 mmol) was dissolved in dry THF (600 mL) and the mixture was cooled to -65 C in a dry ice acetone bath. A n-BuLi hexane solution (1.6 M: 93.7 mL, 150 mmol) was added with stirring and the mixture was stirred at the same temperature for 30 min. After stirring, a cooled (10 C) solution of 9a (38.03 g, 144 mmol) in dry THF (2.88 L) was added at not more than -55 C and the mixture was stirred for 20 min. An additional n-BuLi hexane solution (1.6 M: 94.5 mL, 151 mmol) was added at not more than -65 C and the mixture was further stirred for 30 min. To the mixture, a solution of 6 (14.66 g, 120 mmol) in a dry THF solution (240 mL) was added dropwise and the resulting solution was stirred at the same temperature for 1.5 h. After dilution with saturated aqueous ammonium chloride solution, the mixture was concentrated under reduced pressure. The resulting residue was dissolved in ethanol and the insoluble material was filtered off. The filtrate was concentrated under reduced pressure and the resulting residue was chromatographed on silica gel (CHCl3/7% ammonia in MeOH = 19:1 to 9:1) and recrystallized from MeOH to give 3c (16.44 g, 45%) as a colorless powder. The spectral data were identical to those of the authentic sample.

References: [1]Bioorganic and Medicinal Chemistry,2011,vol. 19,p. 6356 - 6374.

11
[ 426219-35-4 ]
[ 89525-40-6 ]
[ 1416216-55-1 ]

References: [1]Patent: WO2012/173280,2012,A1 .

12
[ 426219-35-4 ]
[ 89525-40-6 ]
[ 1416216-54-0 ]

Yield	Reaction Conditions	Operation in experiment
		Example 26Under a nitrogen atmosphere, 6-bromo-N-methyl-2- naphthamide (5.0 g, 18.9 mmol) was added to tetrahydrofuran (125 mli), and to the obtained solution was added dropwise 2.0 mol/L isopropylmagnesium chloride tetrahydrofuran solution(9.5 mL) at room temperature. The obtained reaction mixture was cooled to -30C, 1.65 mol/L n-butyllithium hexane solution (18.9 mL) was added dropwise thereto, and the mixture was stirred at the same temperature for 1 hr or more. To the reaction mixture was added dropwise a solution of t-butyl 4- formyl-lH-imidazole-l-carboxylate (6.7 g, 34.1 mmol) intetrahydrofuran (50 mL) at -20C, and the mixture was stirred at the same temperature for 2 hr. The obtained reactionmixture was warmed over 2 hr to 0C, and 20w/v% aqueousammonium chloride solution (75 mL) was added dropwise thereto. The separated organic layer was concentrated to the volume of about 65 mL under reduced pressure to give a residue. To the obtained residue was added tetrahydrofuran (100 mL) , and the mixture was concentrated to the volume of about 65 mL under reduced pressure to give a residue. To the obtained residue was added acetone (100 mL) , and the mixture was concentrated to the volume of about 100 mL under reduced pressure . These operations were repeated three times to give a residue. The obtained residue was concentrated to dryness to give t-butyl 4- (hydroxy ( 6-methylcarbamoyl) naphthalen-2-yl) methyl) -1H- imidazole-l-carboxylate (10.5 g) . HRMS (ESI) m/z Calcd for a C21H24 3O [m+H] 382.1722, Found:382.1759.

References: [1]Patent: WO2012/173280,2012,A1 .Location in patent: Page/Page column 60.

13
[ 426219-35-4 ]
[ 140174-48-7 ]
[ 1416216-42-6 ]

Yield	Reaction Conditions	Operation in experiment
		Example 12Under a nitrogen atmosphere, .6-bromo-N-methyl-2- naphthamide (10.0 g, 38 mmol) was added to tetrahydrofuran (250 mL) , and then 2.0 mol/L isopropylmagnesium chloride tetrahydrofuran solution (19 mL) was added dropwise thereto at room temperature. The obtained reaction mixture was cooled to -20C, 1.6 mol/L n-butyllithium hexane solution (40 mL) was added dropwise to the reaction mixture, and the mixture was stirred at the same temperature for 2 hr. To the obtained reaction mixture was added dropwise a solution of 1-N,N- dimethylaminosulfonyl-4-formyl-lH-imidazole (11.6 g, 57 mmol) in tetrahydrofuran (200 mL) at -20C, and the mixture was stirred at the same temperature for 2 hr. The obtained reaction mixture was allowed to warm to 0C, and stirred for 1 hr, and 20w/v% aqueous ammonium chloride solution (150 mL) was added dropwise to the reaction mixture. The reaction mixture was separated to the organic layer and aqueous layer, and the obtained organic layer was concentrated to the volume of about 90 mL under reduced pressure. To the obtained residue was added tetrahydrofuran (140 mL) , and the obtained reaction mixture was concentrated to the volume of about 80 mL under reduced pressure. To the obtained residue was added ethyl acetate (250 mL) , and the mixture was concentrated to the volume of about 80 mL under reduced pressure. These operations were repeated three times. To the obtained residue was added ethyl acetate to adjust the volume to about 200 mL to give a ethyl acetate solution containing 6- [hydroxy ( 1-N, N- dimethylaminosulfonyl-lH-imidazol-4-yl) methyl] -N-methyl-2- naphthamide .The NMR data of the obtained 6- [hydroxy ( 1-N, N- dimethylaminosulfonyl-lH-imidazol-4-yl) methyl] -N-methyl-2- naphthamide was shown below.XH NMR (500 MHz, DMSO-d6) delta 2.76-2.88 (m, 9H) , 5.82 (s, lH) , 6.08 (s, 1H) , 7.37-7.43 (m, 1H) , 7.61 (dd, J = 8.5, 1.58 Hz, 1H), 7.84-8.02 (m, 4H) , 8.07 (d, J = 1.3 Hz, 1H) , 8.39 (s, 1H) , 8.59 (d, J = 4.1Hz, 1H) ; HRMS (ESI) m/z Calcd for aC18H21 4O4S [m+H] + : 389.1205, Found: 389.1273

References: [1]Patent: WO2012/173280,2012,A1 .Location in patent: Page/Page column 46.

14
[ 426219-35-4 ]
[ 37622-92-7 ]
[ 1416216-46-0 ]

Yield	Reaction Conditions	Operation in experiment
52%		Example 16Under a nitrogen atmosphere, 6-bromo-N-methyl-2- .naphthamide (10.0 g, 37.9 mmol) was added to tetrahydrofuran(250 mL) , and to the obtained solution was added dropwise 2.0 mol/L isopropylmagnesium chloride tetrahydrofuran solution(18.9 mL) at room temperature. The obtained reaction mixture was cooled to -30C, 1.65 mol/L n-butyllithium hexane solution (37.9 mL) was added dropwise thereto, and the mixture was stirred at the same temperature for 1 hr or more. To the obtained reaction mixture was added dropwise a solution of 1- tosyl-4-formyl-lH-imidazole (14.2 g, 56.8 mmol) intetrahydrofuran (200 mL) at -20C, and the mixture was stirred at the same temperature for 2 hr. The obtained reactionmixture was warmed over 2 hr to 0C, 20w/v% aqueous ammonium chloride solution (150 mL) was added dropwise thereto. The separated organic layer was concentrated to the volume of about 130 mL under reduced pressure to give a residue. To the obtained residue was added tetrahydrofuran (200 mL) , and the mixture was concentrated to the volume of about 130 mL under reduced pressure to give a residue. To the obtained residue was added acetone (200 mL) , and the mixture was concentrated to the volume of about 200 mL under reduced pressure. These operations were repeated three times to give a residue. To the obtained residue was added acetone to adjust the volume to about 260 mL. The obtained solution was1 stirred at room temperature for 2 hr or more. The obtained crystals were collected by filtration, and washed with acetone (100 mL) to. give wet crystals. The obtained wet crystals were dried under reduced pressure at an outside temperature of 50C to give 6- (hydroxy (l-tosyl-lH-imidazdl-4-yl)methyl) -N-methyl-2- naphthamide (8.5 g, 19.5 mmol)". yield 52%.ChiEta NMR (500 MHz, DMSO-d6) delta 2.40 (s, 3H) , 2.83 (d, J = 5.0 Hz, 1H) , 5.74 (d, J = 5.0 Hz, 1H) , 6.05 (d, J = 5.0 Hz, 1H) , 7.49- 7.51 (m, 3H) , 7.55-7.56 (m, 1H) , 7.88-7.92 (m, 4H) , 7.98-7.99 (m, 2H) , 8.27 (s, 1H) , 8.37 (s, 1H) , 8.58-8.59 (q, J = 5.0 Hz, 1H); HRMS (ESI) m/z Calcd for a C23H22N3O4S [m+H] +: 436.1286, Found: 436.1322.

References: [1]Patent: WO2012/173280,2012,A1 .Location in patent: Page/Page column 50-51.

15
[ 426219-35-4 ]
[ 337521-39-8 ]

References: [1]Patent: WO2012/173280,2012,A1 .
[2]Patent: EP1471056,2004,A1 .

16
[ 426219-35-4 ]
[ 566200-78-0 ]

References: [1]Patent: WO2012/173280,2012,A1 .

17
[ 426219-35-4 ]
[ 566200-79-1 ]

References: [1]Patent: WO2012/173280,2012,A1 .
[2]Patent: EP1471056,2004,A1 .
[3]Patent: EP1471056,2004,A1 .
[4]Patent: EP1471056,2004,A1 .
[5]Patent: EP1471056,2004,A1 .
[6]Patent: EP1471056,2004,A1 .
[7]Patent: EP1471056,2004,A1 .
[8]Patent: EP1471056,2004,A1 .

18
[ 426219-35-4 ]
[ 1416216-41-5 ]

References: [1]Patent: WO2012/173280,2012,A1 .
[2]Patent: WO2012/173280,2012,A1 .

19
[ 426219-35-4 ]
[ 1416216-43-7 ]

References: [1]Patent: WO2012/173280,2012,A1 .

20
[ 426219-35-4 ]
[ 1416216-44-8 ]

References: [1]Patent: WO2012/173280,2012,A1 .

21
[ 426219-35-4 ]
[ 1416216-45-9 ]

References: [1]Patent: WO2012/173280,2012,A1 .

22
[ 426219-35-4 ]
[ 1416216-47-1 ]

References: [1]Patent: WO2012/173280,2012,A1 .

23
[ 426219-35-4 ]
[ 1416216-48-2 ]

References: [1]Patent: WO2012/173280,2012,A1 .

24
[ 426219-35-4 ]
[ 1416216-49-3 ]

References: [1]Patent: WO2012/173280,2012,A1 .

25
[ 426219-35-4 ]
[ 1416216-51-7 ]

References: [1]Patent: WO2012/173280,2012,A1 .

26
[ 426219-35-4 ]
[ 1416216-52-8 ]

References: [1]Patent: WO2012/173280,2012,A1 .

27
[ 426219-35-4 ]
[ 1416216-53-9 ]

References: [1]Patent: WO2012/173280,2012,A1 .

28
[ 426219-35-4 ]
[ 1416216-56-2 ]
[ 1416216-50-6 ]

Yield	Reaction Conditions	Operation in experiment
58%	With n-butyllithium; isopropylmagnesium chloride; In tetrahydrofuran; hexane; at -30℃;Inert atmosphere;	Example 22 Under a nitrogen atmosphere, 6-bromo-N-methyl-2- naphthamide (10.0 g, 37.9 mmol) was added to tetrahydrofuran (250 mL) , and to the obtained solution was added dropwise 2.0 mol/L isopropylmagnesium chloride tetrahydrofuran solution (18.9 mL) at room temperature. The obtained reaction mixture was cooled to -30C, 1.65 m l/L n-butyllithium hexane solution (37.9 mL) was added dropwise thereto, and the mixture was stirred at the same temperature for 1 hr or more. To the reaction mixture was added dropwise a solution of 1- (phenylsulfonyl) -4-formyl-lH-imidazole (13.4 g, 56.8 mmol) in tetrahydrofuran (100 mL) at -20C, and the mixture was stirred at the same temperature for 2 hr. The reaction mixture was warmed over 2 hr to 0C, and 20w/v% aqueous ammonium chloride solution (150 mL) was added dropwise thereto. The separated ' organic layer was concentrated to the volume of about 130 mL under reduced pressure to give a residue. To the obtained residue was added tetrahydrofuran (200 mL) , and the mixture was concentrated to the volume of about 130 mL under reduced pressure to give a residue. To the obtained residue was added ethyl acetate (200 mL) , and the mixture was concentrated to the volume of about 200 mL under reduced pressure. These operations were repeated three times to give a residue. To the obtained residue was added ethyl acetate to adjust the volume to about 200 mL. The obtained reaction mixture was stirred at room temperature for 2 hr or more to give crystals. The crystals was collected by filtration, and washed with ethyl acetate (100 mL) to give wet crystals. The obtained wet crystals were dried under reduced pressure at an outside temperature of 50C to give 6- (hydroxy (1- (phenylsulfonyl) -1H- imidazol-4-yl)methyl) -N-methyl-2-naphthamide (9.2 g, 21.8 mmol) . yield 58% .1ti NMR (500 MHz, DMSO-d6) delta 2.83 (d, J = 5.0 Hz, 3H) , 5.74 (d, J = 5.0 Hz, 1H), 6.06 (d, J = 5.0 Hz, 1H) , 7.69-7.72 (m, 2H) , 7.81-7.84 (m, 1H) , 7.90-7.94 (m, 4H) , 8.11-8.13 (m, 2H) , 8.30 (s, 1H) , 8.37 (s, 1H) , 8.57-8.59 (q, 1H) .

References: [1]Patent: WO2012/173280,2012,A1 .Location in patent: Page/Page column 55-56.

29
[ 426219-35-4 ]
[ 426219-18-3 ]

References: [1]Patent: EP1471056,2004,A1 .
[2]Patent: EP1471056,2004,A1 .
[3]Patent: EP1471056,2004,A1 .
[4]Patent: EP1471056,2004,A1 .
[5]Patent: EP1471056,2004,A1 .
[6]Patent: EP1471056,2004,A1 .
[7]Patent: EP1471056,2004,A1 .
[8]Patent: EP1471056,2004,A1 .
[9]Patent: EP1471056,2004,A1 .
[10]Patent: EP1471056,2004,A1 .

30
[ 426219-35-4 ]
[ 566200-77-9 ]

References: [1]Patent: EP1471056,2004,A1 .
[2]Patent: EP1471056,2004,A1 .
[3]Patent: EP1471056,2004,A1 .

31
[ 426219-35-4 ]
ethyl 3-hydroxy-3-{6-[(methylamino)carbonyl]-2-naphthyl}-3-(1-trityl-1H-imidazol-4-yl)propanoate [ No CAS ]

References: [1]Patent: EP1471056,2004,A1 .

32
[ 426219-35-4 ]
isopropyl (3S)-3-hydroxy-3-{6-[(methylamino)carbonyl]-2-naphthyl}-3-(1-trityl-1H-imidazol-4-yl)propanoate [ No CAS ]

References: [1]Patent: EP1471056,2004,A1 .

33
[ 426219-35-4 ]
[ 566200-98-4 ]

References: [1]Patent: EP1471056,2004,A1 .
[2]Patent: EP1471056,2004,A1 .

34
[ 426219-35-4 ]
methyl (3S)-3-hydroxy-3-{6-[(methylamino)carbonyl]-2-naphthyl}-3-(1-trityl-1H-imidazol-4-yl)propanoate [ No CAS ]

References: [1]Patent: EP1471056,2004,A1 .

35
[ 426219-35-4 ]
ethyl (3S)-3-hydroxy-3-{6-[(methylamino)carbonyl]-2-naphthyl}-3-(1-trityl-1H-imidazol-4-yl)propanoate [ No CAS ]

References: [1]Patent: EP1471056,2004,A1 .
[2]Patent: EP1471056,2004,A1 .
[3]Patent: EP1471056,2004,A1 .
[4]Patent: EP1471056,2004,A1 .
[5]Patent: EP1471056,2004,A1 .

Historical Records

Technical Information

• Acyl Group Substitution • Alkyl Halide Occurrence • Benzylic Oxidation • Birch Reduction • Blanc Chloromethylation • Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions • Chan-Lam Coupling Reaction • Complex Metal Hydride Reductions • Friedel-Crafts Reaction • General Reactivity • Grignard Reaction • Hiyama Cross-Coupling Reaction • Hydride Reductions • Hydrogenolysis of Benzyl Ether • Kinetics of Alkyl Halides • Kumada Cross-Coupling Reaction • Lawesson's Reagent • Leuckart-Wallach Reaction • Mannich Reaction • Petasis Reaction • Preparation of Alkylbenzene • Preparation of Amines • Reactions of Alkyl Halides with Reducing Metals • Reactions of Amines • Reactions of Benzene and Substituted Benzenes • Reactions of Dihalides • Specialized Acylation Reagents-Carbodiimides and Related Reagents • Specialized Acylation Reagents-Ketenes • Specialized Acylation Reagents-Vilsmeier Reagent • Stille Coupling • Substitution and Elimination Reactions of Alkyl Halides • Suzuki Coupling • Ugi Reaction • Vilsmeier-Haack Reaction

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[ 426219-35-4 ]

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H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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CAS No.: 426219-35-4

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CAS No.: 426219-35-4

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Physicochemical Properties

Lipophilicity

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Druglikeness

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Application In Synthesis of [ 426219-35-4 ]

[ 426219-35-4 ] Synthesis Path-Downstream 1~35

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[ 426219-35-4 ]

Aryls

Bromides

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{[proInfo.proName]}

CAS No.: 426219-35-4

{[proInfo.proName]}

CAS No.: 426219-35-4

Alternative Products

Product Details of [ 426219-35-4 ]

Safety of [ 426219-35-4 ]

Computational Chemistry of [ 426219-35-4 ] Show Less

Physicochemical Properties

Lipophilicity

Water Solubility

Pharmacokinetics

Druglikeness

Medicinal Chemistry

Application In Synthesis of [ 426219-35-4 ]

[ 426219-35-4 ] Synthesis Path-Downstream 1~35

Related Products

Historical Records

Technical Information

Categories

Related Functional Groups of [ 426219-35-4 ]

Aryls

Bromides

Amides

Amines

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Molarity Calculator

Total Compounds Calculator

Dissolution Calculator

Related Functional Groups of
[ 426219-35-4 ]