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[ CAS No. 2734-70-5 ] {[proInfo.proName]}

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Chemical Structure| 2734-70-5
Chemical Structure| 2734-70-5
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Product Details of [ 2734-70-5 ]

CAS No. :2734-70-5 MDL No. :MFCD00053934
Formula : C8H11NO2 Boiling Point : No data available
Linear Structure Formula :- InChI Key :HQBJSEKQNRSDAZ-UHFFFAOYSA-N
M.W : 153.18 Pubchem ID :95940
Synonyms :

Calculated chemistry of [ 2734-70-5 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.25
Num. rotatable bonds : 2
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 43.83
TPSA : 44.48 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.65 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.89
Log Po/w (XLOGP3) : 0.82
Log Po/w (WLOGP) : 1.29
Log Po/w (MLOGP) : 0.87
Log Po/w (SILICOS-IT) : 1.09
Consensus Log Po/w : 1.19

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.58
Solubility : 4.05 mg/ml ; 0.0264 mol/l
Class : Very soluble
Log S (Ali) : -1.34
Solubility : 7.06 mg/ml ; 0.0461 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.28
Solubility : 0.809 mg/ml ; 0.00528 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.26

Safety of [ 2734-70-5 ]

Signal Word:Warning Class:
Precautionary Statements:P305+P351+P338 UN#:
Hazard Statements:H302-H319 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 2734-70-5 ]

* 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 [ 2734-70-5 ]

[ 2734-70-5 ] Synthesis Path-Downstream   1~12

  • 1
  • [ 463-71-8 ]
  • [ 2734-70-5 ]
  • [ 343790-65-8 ]
YieldReaction ConditionsOperation in experiment
92% With sodium hydrogencarbonate; In dichloromethane; water; at 20℃; for 1.16667h;Cooling with ice; To a mixed solution of dichloromethane (500 mL) and water (500 mL) , 2 , 6-dimethoxyaniline (75.8 g, 495 mmol) and sodium hydrogen carbonate (83.1 g, 990 mmol) were added, and thiophosgene (62.6 g, 544 mmol) was added in small portions with stirring under ice cooling. The mixture was stirred for 10 minutes under ice cooling and then stirred at room temperature for 1 hour. An organic layer was separated, and dichloromethane was added to the aqueous layer to extract organic matter. The organic layers were combined, washed with saturated saline, and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. Then, n-hexane was added to the obtained solid, and the resulting solid was collected by filtration to obtain the title compound (88.5 g, 454 mmol, 92%) as a white solid. 1H-NMR (400 MHz, CDC13) δ (ppm) : 3.89 (6H, s), 6.54 (2H, d, J = 8.5 Hz), 7.14 (1H, t, J = 8.5 Hz). MS (APCI): m/z 182 [M+H]+.
86% With 2,6-dimethylpyridine; In dichloromethane; at 0℃; for 2h; 2-isothiocyanato-1,3-dimethoxybenzene, Example 1.0. To a solution of <strong>[2734-70-5]2,6-dimethoxyaniline</strong> (500 g, 3.25 mol, 1 eq) in DCM (5.0 L) was added 2,6-lutidine (1.5 L, 13.0 mol, 4 eq). The reaction mixture was cooled to 0 C (internal temperature) and CSC12 (374 mL, 4.88 mol, 1.5 eq) was added drop-wise. The reaction mixture was allowed to stir for 2 h. The solvent was evaporated under reduced pressure and the residue was purified on silica gel to provide the title compound 1.0, 2-isothiocyanato-1,3- dimethoxybenzene as white solid (1.06 g, 2.80 mol, 86%). LCMS (ESI pos. ion) mlz:196 (M+H). ‘H NMR (400 MI-Tz, CDC13) 7.16 (t, J 8.48 Hz, 1H), 6.55 (d, J 8.48 Hz, 2H), 3.90 (s, 6H).
86% With 2,6-dimethylpyridine; In dichloromethane; at 0℃; for 2h; 2-Isothiocyanato-1,3-dimethoxybenzene, Example 10.0 To a solution of <strong>[2734-70-5]2,6-dimethoxyaniline</strong> (500 g, 3.25 mol, 1 eq) in DCM (5.0 L) was added 2,6-Lutidine (1.5 L, 13.0 mol, 4 eq). The reaction mixture was cooled to 0 C. (internal temperature) and CSCl2 (374 mL, 4.88 mol, 1.5 eq) was added drop-wise. The reaction mixture was allowed to stir for 2 h. The solvent was then evaporated under reduced pressure and the material thus obtained was purified by SiO2 column to provide Example 10.0, 2-isothiocyanato-1,3-dimethoxybenzene, as a white solid (1.06 g, 2.80 mol, 86%). LCMS (ESI pos ion) m/z: (M+H)+=196. 1H NMR (400 MHz, CDCl3) δ 7.16 (t, J=8.48 Hz, 1H), 6.55 (d, J=8.48 Hz, 2H), 3.90 (app s, 6H).
86% With 2,6-dimethylpyridine; In dichloromethane; at 0℃; for 2h; To a solution of <strong>[2734-70-5]2,6-dimethoxyaniline</strong> (500 g, 3.25 mol, 1 eq) in DCM (5.0 L) was added 2,6- lutidine (1.5 L, 13.0 mol, 4 eq). The reaction mixture was cooled to 0 C (internal temperature) and CSCl2(374 mL, 4.88 mol, 1.5 eq) was added dropwise. The reaction mixture was then stirred for 2 h. The solvent was evaporated under reduced pressure, and the material thus obtained was purified by silica column to provide the title compound, 2- isothiocyanato-1,3-dimethoxybenzene, Example 465.0 as a white solid (1.06g, 2.80 mol, 86%).1H NMR (400 MHz, CDCl3) δ 7.16 (t, J = 8.48 Hz, 1H), 6.55 (d, J = 8.48 Hz, 2H), 3.90 (m, 6H). LCMS (ESI pos. ion) m/z: (M+H)+196.
86% With 2,6-dimethylpyridine; In dichloromethane; at 0℃; for 2h; To a solution of <strong>[2734-70-5]2,6-dimethoxyaniline</strong> (500 g, 3.25 mol, 1 eq) in DCM (5.0 L) was added 2,6-lutidine (1.5 L, 13.0 mol, 4 eq). The reaction mixture was cooled to 0 C (internal temperature) and CSCl2 (374 mL, 4.88 mol, 1.5 eq) was added drop-wise. The reaction mixture was allowed to stir for 2 h. The solvent was evaporated under reduced pressure and the initial product was purified by SiO2 column to provide the title compound, 2-isothiocyanato-1,3- dimethoxybenzene, Example 1.2 as white solid (1.06g, 2.80 mol, 86%). LCMS (ESI pos. ion) m/z: (M+H)+ = 196. 1H NMR (400 MHz, CDCl3) δ 7.16 (t, J = 8.48 Hz, 1H), 6.55 (d, J = 8.48 Hz, 2H), 3.90 (m, 6H).
86% With 2,6-dimethylpyridine; In dichloromethane; at 0℃; for 2h; To a solution of <strong>[2734-70-5]2,6-dimethoxyaniline</strong> (500 g, 3.25 mol, 1 eq) in DCM (5.0 L) was added 2,6-lutidine (1.5 L, 13.0 mol, 4 eq). The reaction mixture was cooled to 0 C (internal temperature) and CSC12 (374 mL, 4.88 mol, 1.5 eq) was added dropwise. The reaction mixture was then stirred for 2 h. The solvent was evaporated under reduced pressure and the material thus obtained was purified by SiC column to provide the title compound, 2-isothiocyanato-l,3-dimethoxybenzene, Example 82.0 as a white solid (1.06g, 2.80 mol, 86%). LCMS (ESI pos. ion) m/z: (M+H)+ = 196. NMR (400 MHz, CDCI3) δ 7.16 (t, J= 8.48 Hz, 1H), 6.55 (d, J = 8.48 Hz, 2H), 3.90 (m, 6H).
86% With 2,6-dimethylpyridine; In dichloromethane; at 0℃; for 2h;Inert atmosphere; To a solution of <strong>[2734-70-5]2,6-dimethoxyaniline</strong> (500 g, 3.25 mol, 1 eq) in DCM (5.0 L) was added 2,6- lutidine (1.5 L, 13.0 mol, 4 eq). The reaction mixture was cooled to 0 C (internal temperature) and CSC12 (374 mL, 4.88 mol, 1.5 eq) was added dropwise. The reaction mixture was then stirred for 2 h. The solvent was evaporated in vacuo and the initial mass was purified by Si02 column to provide the title compound, Example 372.0, as a white solid (1.06g, 2.80 mol, 86%). LCMS (ESI pos. ion) m/z: (M+1)+ = 196. 1HNMR (400 MHz, CDC13) ? 7.16 (t,J= 8.48 Hz, 1H), 6.55 (d,J= 8.48 Hz, 2H), 3.90 (m, 6H).
53% With sodium hydrogencarbonate; In dichloromethane; water; at 0 - 20℃; for 1.16667h; To a mixture of dichloromethane (50 mL) and water (50 mL) were added 2,6- dimethoxyaniline (4.6 g, 30 mmol, 1 equiv) and sodium bicarbonate (5.0 g, 60 mmol, 2 equiv). Then thiophosgene (2.6 mL, 33 mmol, 1.1 equiv) was added in small portions with stirring at 0C. After addition, the mixture was stirred for 10 mins at 0C and then at room temperature for 1 hour. The organic layer was separated and the aqueous layer was extracted with DCM (2*50 mL). The combined organic extracts were washed with brine (30 mL), dried over anhydrous Na2S04, filtered and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (eluted with PE/EtOAc = 200/1) to afford the title compound 2-isothiocyanato-l,3-dimethoxybenzene as an off-white solid (3.1 g, 53% yield). NMR (400 MHz, DMSO-de) d: 7.29 (t, J = 8.0 Hz, 1H), 6.76 (d, J = 8.0 Hz, 2H), 3.86 (s, 6H). LC-MS: m/z 196.1 (M+H)+
With 2,6-dimethylpyridine; In dichloromethane; at 0℃; for 2h; To a solution of <strong>[2734-70-5]2,6-dimethoxyaniline</strong> (500 g, 3.25 mol, 1 eq) in DCM (5.0 L) was added 2,6- lutidine (1.5 L, 13.0 mol, 4 eq). The reaction mixture was cooled to 0 C (internal temperature) and CSC12 (374 mL, 4.88 mol, 1.5 eq) was added drop-wise. The reaction mixture was allowed to stir for 2 h. The solvent was then evaporated in vacuo, and the initial mass was purified by Si02 column to provide 2-isothiocyanato-1,3- dimethoxybenzene, Example 28.0 as white solid. LCMS-ESI (pos.) m/z: (M+H) = 196. 1H NMR (400 MHz, CDC13) ? 7.16 (t, J= 8.48 Hz, 1H), 6.55 (d, J= 8.48 Hz, 2H), 3.90 (app s, 6H).

  • 2
  • [ 6665-97-0 ]
  • [ 2734-70-5 ]
YieldReaction ConditionsOperation in experiment
98% With iron(0); glacial acetic acid; In ethanol; water monomer; at 90℃; To a solution of 78 (170 mg, 0.93 mmol) in AcOH (5 mL), EtOH (5 mL) and H2O (2.5 mL) was added iron powder (311 mg, 325 mesh, 5.57 mmol) portion wise. The mixture was then heated at 90 C. under N2 overnight. After cooling to room temperature, the mixture was poured onto ice, basified using solid Na2CO3 and extracted with EtOAc (3×). The combined organic layers were washed with brine, dried over Na2SO4 and concentrated in vacuo to yield 79 as a pale yellow solid (139 mg, 98%). MS (APCD): m/z 154 (100%, [M+H]+) which was used in the next step without further purification.
80% With palladium 10% on activated carbon; hydrogen; In ethanol; at 20 - 30℃; under 7500.75 Torr;Autoclave; In a 150-ml autoclave, 2,6-dimethoxynitrobenzene (10 g, 55 mmol) was added in that order,30ml absolute ethanol,0.2 g of 10% Pd / C catalyst,Into high purity hydrogen to 1.0MPa,Reaction at room temperature.When the hydrogen pressure gauge is not falling as the end of the reaction.Filtration, the filtrate spin dry,A white solid 6.7g, 80% yield.
60% With hydrogenchloride; dichloro-λ2-stannane dihydrate; In diethyl ether; at 20℃; for 30.0h; To conc. hydrochloric acid (15 mL) was added dihydrated tin chloride (69.6 g, 308 mmol) at rt. In another flask, compound 50 (5.6 g, 30.6 mmol) was solubilized in ethyl ether (60 mL). The resulting mixture was added by small portions to dissolved tin chloride in hydrochloric acid. The reaction was run to completion over 12 hours at rt. The mixture was then poured into cold water and basified to pH = 9 with aqueous sodium hydroxide and stirred at rt for 3 hours. The final suspension was filtered on Celite. After dilution of the filtrate with ethyl acetate and washing with water, the organic layer was dried over MgSO4 and concentrated under reduced pressure. The off-white solid obtained 51 (2.81 g, 60%) presented the same physico-chemical properties as the commercial product. TLC Rf (EtOAc) = 0.83; 1H NMR (CDCl3, 400 MHz) δ (ppm) 3.81 (s, 2H, NH2), 3.86 (s, 6H, 2OCH3), 6.53 (d, J = 8.2 Hz, 2H, ArH), 6.69 (t, J = 8.2 Hz, 1H, ArH).
With iron(0); glacial acetic acid; In ethanol; water monomer; at 90℃;Inert atmosphere; 2,6-Dimethoxy-phenylamine (79): To a solution of 78 (170 mg, 0.93 mmol) in AcOH (5 mL), EtOH (5 mL) and H2O (2.5 mL) was added iron powder (311 mg, 325 mesh, 5.57 mmol) portion wise. The mixture was then heated at 90 C. under N2 overnight. After cooling to room temperature, the mixture was poured onto ice, basified using solid Na2CO3 and extracted with EtOAc (3×). The combined organic layers were washed with brine, dried over Na2SO4 and concentrated in vacuo to yield 79 as a pale yellow solid (139 mg, 98%). MS (APCI): m/z 154 (100%, [M+H]+) which was used in the next step without further purification.

  • 3
  • [ 2734-70-5 ]
  • [ 108-24-7 ]
  • [ 131157-26-1 ]
YieldReaction ConditionsOperation in experiment
60% In dichloromethane; at 20℃; for 24h;Inert atmosphere; Acetic anhydride (2.97 mL, 31.45 mmol) was added to a solution of aniline 51 (2.19 g, 14.3 mmol) in dry dichloromethane (50 mL) under inert atmosphere. The reaction was stirred at room temperature for 24 hours. Upon completion, the reaction mixture was washed with a saturated solution of sodium carbonate, the organic layer dried over MgSO4 and the solvent removed under reduced pressure. The acetanilide 52 was obtained as a white solid (1.67 g, 60%) after crystallization from Et2O; mp (Et2O) 128-130 C; TLC Rf (EtOAc) = 0.37; 1H NMR (CDCl3, 400 MHz) δ (ppm) 2.20 (large s, 3H, NHCOCH3), 3.84 (s, 6H, 2OCH3), 6.42 (large s, 1H, NHCOCH3), 6.59 (d, J = 8.4 Hz, 2H, ArH), 7.20 (t, J = 8.2 Hz, 1H, ArH). 13C NMR (CDCl3, 100 MHz) δ 23.3 (CH3), 55.9 (2CH3), 104.3 (2CH), 107.4 (C), 127.8 (CH), 155.6 (2C), 172.9 (C). IR ν cm-1: 1104, 1253, 1437, 1474, 1537, 1590, 1651, 3184, 3256. Calcd. for C10H13O3N: C, 61.53; H, 6.71; N, 7.17. Found: C, 61.36; H, 6.94; N, 7.01.
  • 4
  • [ 573-54-6 ]
  • [ 2734-70-5 ]
  • [ 103942-80-9 ]
  • 7
  • [ 2734-70-5 ]
  • [ 598-21-0 ]
  • 2-bromo-<i>N</i>-(2,6-dimethoxy-phenyl)-acetamide [ No CAS ]
  • 8
  • [ 2734-70-5 ]
  • N-(2,6-dimethoxyphenyl)-2-(2-methoxybenzyl)-3-oxoisoindoline-1-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
17% To a solution of 2-(2-methoxybenzyl)-3-oxoisoindoline-l-carboxylic acid (59mg, 0.2 mmol), and NEt3 (84 μL, 0.3 mmol) in DMF (2 mL), N,N,N',N'-tetramethyl- fluoroformamidinium hexafluuorophosphate (79mg, 0.3 mmol) was added, and the mixture was stirred at room temperature for 30min. 2,6-Dimethoxyaniline (46 mg, 0.3 mmol) was added in one portion, and the reaction mixture was heated at 50 0C for 45 min. The mixture was cooled down to room temperature, filtered, and purified by preparative HPLC to yield the title compound (15 mg, 17%).
  • 10
  • [ 263854-44-0 ]
  • [ 2734-70-5 ]
  • [ 263849-96-3 ]
YieldReaction ConditionsOperation in experiment
55% With N-ethyl-N,N-diisopropylamine; HATU; In DMF (N,N-dimethyl-formamide); Thymol (1.0 eq, 33.3mmol) and methyl 5-(chloromethyl)-2-furoate (1.0 eq, 33.3mmol) were dissolved in nitromethane (120mL, 0.2M). Aluminum trichloride (1.0 eq, 33.3mmol) dissolved in 25mL nitromethane was added to the above solution under nitrogen and heated to slow reflux over 10 min. The heat was turned off and left under nitrogen overnight. The reaction was quenched with 100mL of water and exctracted with dichloromethane. The crude mixture was evaporated to dryness and loaded onto plug chromatography column (1g crude/100g silica gel ratio). The column was eluted with 7 and 11% ethyl acetate/hexanes to yield the desired product (2.9 g, 30%). The ester was hydrolyzed to acid by lithium hydroxide in THF/MeOH/H2O (35/25/25). To a solution containing the 5-(4-hydorxy-5-isopropyl-2-methylbenzyl)-2-furoic acid (1.0eq, 3.6 mmol, 0.5M), and <strong>[2734-70-5]2,6-dimethoxyaniline</strong> (1.0eq, 3.6mmol) were dissolved in DMF. To this mixture, HATU (1.0 eq, 3.6 mmol) and di-isopropyl ethyl amine (1.0 eq, 3.6 mmol) were added and stirred overnight. The mixture was heated for 10min at 45C. The solution was placed into ethyl acetate (3x volume) and washed with water. The organic layer was evaporated to syrup and eluted on plug column chromatography (1:100 g crude/g silicagel) with 30 and 50 % ethyl acetate/hexane to yield: N-(2,6-dimethoxyphenyl)-5-(4-hydroxy-5-isopropyl-2-methylbenzyl)-2furamide (820 mgs, 55% yield). 1HNMR (CDCl3) 7.22ppm (1H, t, J=8.68 Hz), 7.08ppm (1H, d, J=3.40 Hz), 6.99ppm (1H,s), 6.64ppm (2H, d, J=8.68 Hz), 6.61ppm (1H, s), 5.97 ppm (1H, d, J=3.40 Hz), 3.95ppm, (2H,s), 3.85ppm, (6H,s), 3.17ppm, (1H,pentet, J=6.8 Hz) 2.23ppm, (3H,s), 1.25 ppm(3H,s), and 1.23ppm (3H, s).
  • 11
  • [ 1466-76-8 ]
  • [ 2734-70-5 ]
YieldReaction ConditionsOperation in experiment
With 4-methyl-morpholine; diphenylphosphoranyl azide; hydrogen; copper(I) iodide; benzyl alcohol;palladium; In methanol; 1,2-dichloro-ethane; Example 16A 2,6-Dimethoxyaniline To a stirred solution of 2,6-dimethoxybenzoic acid (2.00 g, 11.0 mmol) in 1,2-dichloroethane (45 mL) at ambient temperature was successively added N-methylmorpholine (1.45 mL, 13.2 mmol) and diphenylphosphoryl azide (2,60 mL, 12.1 mmol). After heating the mixture for 2 hours at 75 C., cuprous iodide (150 mg) and benzyl alcohol (2.27 mL, 22.0 mmol) were added and heating was continued overnight. Solvents were removed in vacuo and the residue was chromatographed on silica gel, eluding with 4:1 hexane-ethyl acetate to give the intermediate carbamate (1.50 g, 48 % yield) as a white, crystalline solid. The solid was dissolved in methanol (15 mL) and added to a flask purged with nitrogen containing 10% palladium-on-charcoal (500 mg). The mixture was placed under a balloon of hydrogen and stirred 4 hours at ambient temperature. The mixture was filtered through a pad of Celite and solvents were removed in vacuo to give the title compound (800 mg, 48% yield).
  • 12
  • [ 42310-45-2 ]
  • [ 16462-27-4 ]
  • [ 2734-70-5 ]
  • [ 56066-19-4 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; acetic acid; In water; EXAMPLE 11 Preparation of 2,4-Diamino-5-(4-amino-3,5-dimethoxybenzyl)pyrimidine A mixture of 2,4-diamino-5-hydroxymethylpyrimidine (4.30 g, 30.0 mmol), prepared from 2,4-diamino-5-cyanopyrimidine as described in U.K. Pat. No. 1 413 472, <strong>[2734-70-5]2,6-dimethoxyaniline</strong> (5.05 g, 33.0 mmol), acetic acid (60 mL), and concentrated hydrochloric acid (4.2 mL) was refluxed for 41/2 hours, cooled, and filtered to give the hydrochloride salt of the title compound (7.13 g, 76.2%). The salt was dissolved in water and the solution made basic with concentrated ammonium hydroxide. The resulting precipitate was filtered, washed with water, and dried to give the title compound (5.18 g, 62.7%). Calculated for C13 H17 N5 O2: C, 56.72; H, 6.22; N, 25.44. Found: C, 56.63; H, 6.29; N, 25.39.
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