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Chemical Structure| 2393-23-9 Chemical Structure| 2393-23-9

Structure of 2393-23-9

Chemical Structure| 2393-23-9

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Product Citations

Product Citations

Robert Kawȩcki ;

Abstract: N-Sulfenylimines (sulfenimines, thiooximes, N-alkylidenesulfenamides) were efficiently synthesized through the reaction of primary amines and disulfides with NBS or bromine. This reaction can be carried out in an open flask at room temperature without the need for any transition-metal-containing additives. The use of thiols instead of disulfides gave similar results. A wide range of amines were reacted with aryl and alkyldisulfides, resulting in the formation of sulfenimines in a yield of 44–99%.

Alternative Products

Product Details of [ 2393-23-9 ]

CAS No. :2393-23-9
Formula : C8H11NO
M.W : 137.18
SMILES Code : NCC1=CC=C(OC)C=C1
MDL No. :MFCD00008122
InChI Key :IDPURXSQCKYKIJ-UHFFFAOYSA-N
Pubchem ID :75452

Safety of [ 2393-23-9 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H314
Precautionary Statements:P280-P305+P351+P338
Class:8
UN#:2735
Packing Group:

Computational Chemistry of [ 2393-23-9 ] Show Less

Physicochemical Properties

Num. heavy atoms 10
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 40.61
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

35.25 Ų

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

1.7
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

0.84
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

1.0
Log Po/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.

1.21
Log Po/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

1.43
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.24

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-1.53
Solubility 4.03 mg/ml ; 0.0294 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Very soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-1.16
Solubility 9.42 mg/ml ; 0.0687 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

-2.54
Solubility 0.396 mg/ml ; 0.00288 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.

-6.54 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

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)

1.0

Application In Synthesis of [ 2393-23-9 ]

* 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 [ 2393-23-9 ]

[ 2393-23-9 ] Synthesis Path-Downstream   1~35

  • 1
  • [ 121-18-6 ]
  • [ 2393-23-9 ]
  • 4-(4-methoxy-benzylamino)-3-nitro-benzenesulfonic acid [ No CAS ]
  • 3
  • [ 64-19-7 ]
  • [ 2393-23-9 ]
  • [ 104-21-2 ]
  • 4
  • [ 2393-23-9 ]
  • [ 498-63-5 ]
  • [ 203436-45-7 ]
  • 4-formyl-3,5-dimethoxyphenoxymethylpolystyrene resin (PAL) [ No CAS ]
  • {1-[9-isopropyl-6-(4-methoxy-benzylamino)-9<i>H</i>-purin-2-yl]-pyrrolidin-2-yl}-methanol [ No CAS ]
  • 5
  • [ 383-62-0 ]
  • [ 2393-23-9 ]
  • [ 958643-23-7 ]
  • 6
  • [ 5926-51-2 ]
  • [ 2393-23-9 ]
  • [ 1034473-65-8 ]
YieldReaction ConditionsOperation in experiment
Preparation 3 : 3-bromo-1-[4-(methyloxy)phenyl]methyl}-1W-pyrrole-2,5-dione (P3) <n="53"/>A mixture of 3-bromo-2,5-furandione (6 g), 1-[4-(methyloxy)phenyl]methanamine (4.44 mL), and AcOH (80 mL) was heated at 100 0C overnight. The solution was then concentrated in vacuo. AcOH (70 mL) and AcONa (2 g) were added to the crude product and the mixture was reflux for 2 hours. Water was then added and the aqueous phase was extracted with DMC. The organic phase was dried and evaporated in vacuo. The crude was purified by flash chromatography eluting with cyclohexane/ethyl acetate from 9/1 to 7/3 to give the title compound (8.2 g). NMR (1H, CDCI3) delta 7.32 (d, 2H), 6.86 (m, 3H), 4.66 (s, 2H), 3.80 (s, 3H).
  • 7
  • [ 1137475-57-0 ]
  • [ 2393-23-9 ]
  • [ 1184842-88-3 ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In acetonitrile; for 1.5h; Synthesis 1-1 -A N-(4-Methoxybenzyl)-2-bromo-5-nitropyridin-4-amine A solution of 4-methoxybenzylamine (0.756 g, 5.51 mmol) in acetonitrile (2 mL) was added to a mixture of <strong>[1137475-57-0]2-bromo-4-chloro-5-nitropyridine</strong> (1.19 g, 5.01 mmol) and triethylamine (0.768 mL, 5.51 mmol) in acetonitrile (8 mL). After stirring for 1.5 hours, the solution was diluted with ethyl acetate (100 mL) which was then washed successively with water and brine before being concentrated in vacuo to a light brown oil which solidified on standing to give the title compound (1.31 g, 3.87 mmol, 77%). 1H NMR (d6- DMSO, 400 MHz) delta 9.00 (br t, 1 H, J = 6.3 Hz), 8.80 (s, 1 H)1 7.35 (d, 2H, J = 8.7 Hz), 7.10 (s, 1 H), 6.95 (d, 2H, J = 8.8 Hz), 4.60 (d, 2H, J = 6.0 Hz), 3.70 (s, 3H). LCMS (1) Rt = 2.13 min; m/z (ESI-) 336, 338 (M-H).
  • 8
  • [ 927-77-5 ]
  • [ 34595-26-1 ]
  • [ 2393-23-9 ]
  • C23H32N2O [ No CAS ]
  • 9
  • [ 926-62-5 ]
  • [ 34595-26-1 ]
  • [ 2393-23-9 ]
  • [ 1172635-04-9 ]
  • 10
  • [ 351003-49-1 ]
  • [ 2393-23-9 ]
  • [ 1225040-04-9 ]
  • 11
  • [ 24686-78-0 ]
  • [ 2393-23-9 ]
  • [ 536-74-3 ]
  • [ 1227795-14-3 ]
  • 12
  • [ 1794-45-2 ]
  • [ 2393-23-9 ]
  • C17H16ClNO [ No CAS ]
  • 13
  • [ 1184-90-3 ]
  • [ 2393-23-9 ]
  • [ 1415910-61-0 ]
  • 14
  • [ 21906-31-0 ]
  • [ 2393-23-9 ]
  • [ 1176596-11-4 ]
  • 15
  • [ 21906-31-0 ]
  • [ 2393-23-9 ]
  • C17H18BrNO [ No CAS ]
  • 16
  • [ 165111-46-6 ]
  • [ 2393-23-9 ]
  • [ 1440519-96-9 ]
YieldReaction ConditionsOperation in experiment
11.69 g In tetrahydrofuran; at 0 - 20℃; for 16h;Inert atmosphere; To a solution of <strong>[165111-46-6]2-bromomethyl-4-cyano-benzoic acid methyl ester</strong> (18.1 g, 71.24 mmol) in THF (300 mL) was added PMBNH2 (23.4 g, 178.1 mmol) at 0 C and the reaction mixture was stirred at room temperature for 16 hours. After vacuum filtration, the filtrate - 166 -was concentrated in vacuo. The residue obtained was re-dissolved in EtOAc and washed with water and brine. The organic layer was dried over anhy. Na2S04, filtered, and concentrated in vacuo to give a crude product which was purified by columnchromatography (11.69 g, 56.0%) as a soild
56.0 g In tetrahydrofuran; at 0 - 20℃; for 16h;Inert atmosphere; To a solution of <strong>[165111-46-6]2-bromomethyl-4-cyano-benzoic acid methyl ester</strong> (18.1 g, 71.24 mmol) in THF (300 mL) was added PMBNH2 (23.4 g, 178.1 mmol) at 0 C and the reaction mixture was stilTed at room temperature for 16 hours. After vacuum filtration, the filtratewas concentrated in vacuo. The residue obtained was re-dissolved in EtOAc and washed with water and brine. The organic layer was dried over anhy. Na2SO4, filtered, and concentrated in vacuo to give a crude product which was purified by column chromatography to give the title compound (11.69 g, 56.0%) as a solid.
11.69 g In tetrahydrofuran; at 0 - 20℃; for 16h;Inert atmosphere; To a solution of <strong>[165111-46-6]2-bromomethyl-4-cyano-benzoic acid methyl ester</strong> (18.1 g, 71.24 mmol) in THF (300 mL) was added PMBNH2 (23.4 g, 178.1 mmol) at 0 C and the reactionmixture was stilTed at room temperature for 16 hours. After vacuum filtration, the filtrate was concentrated in vacuo. The residue obtained was re-dissolved in EtOAc and washed with water and brine. The organic layer was dried over anhy. Na2SO4, filtered, and concentrated in vacuo to give a crude product which was purified by column chromatography to give the title compound as a solid (11.69 g, 56.0%).
11.69 g In tetrahydrofuran; at 0 - 20℃; for 16h;Inert atmosphere; To a solution of <strong>[165111-46-6]2-bromomethyl-4-cyano-benzoic acid methyl ester</strong> (18.1 g, 71.24 mmol) in THF (300 mL) was added PMBNH2 (23.4 g, 178.1 mmol) at 0 C and the reaction mixture was stilTed at room temperature for 16 hours. After vacuum filtration, the filtratewas concentrated in vacuo. The residue obtained was re-dissolved in EtOAc and washed with water and brine. The organic layer was dried over anhy. Na2SO4, filtered, and concentrated in vacuo to give a crude product which was purified by column chromatography to give the title compound (11.69 g, 56.0%) as a solid.
11.69 g In tetrahydrofuran; at 0 - 20℃; for 16h;Inert atmosphere; GammaRho1 2-(4-Methoxy-benzyl)- l-oxo-2,3-dihvdro-lH-isoindole-5-carbonitrile To a solution of <strong>[165111-46-6]2-bromomethyl-4-cyano-benzoic acid methyl ester</strong> (18.1 g, 71.24 mmol) in THF (300 mL) was added PMBNH2 (23.4 g, 178.1 mmol) at 0 C and the reaction mixture was stirred at room temperature for 16 hours. After vacuum filtration, the filtrate was concentrated in vacuo. The residue obtained was re-dissolved in EtOAc and washed with water and brine. The organic layer was dried over anhy. Na2S04, filtered, and concentrated in vacuo to give a crude product which was purified by silica gel flash chromatography (11.69 g, 56.0%) as a solid.

  • 17
  • [ 117-78-2 ]
  • [ 2393-23-9 ]
  • [ 1596117-61-1 ]
YieldReaction ConditionsOperation in experiment
88% With N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl-formamide; at 20℃; for 2h; A solution of 9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acid (1.00 g, 3.96 mmol) in DMF (15.0 mL) was treated at room temperature with (4- methoxyphenyl)methanamine (1.09 g, 7.93 mmol), HATU (2.26 g, 5.95 mmol) and DIPEA (2.08 mL, 11.9 mmol). The reaction mixture was stirred at room temperature for 2 hours. The mixture was concentrated and purified by Biotage with 0-20percent of MeOH in CH2CI2 to give 1.30 g (88percent) of the title compound as a yellow solid. 1H NMR (400 MHz, DMSO-d6) delta ppm 9.45 (t, J=5.3 Hz, 1 H), 8.67 (t, J=1.8 Hz, 1 H), 8.33 - 8.39 (m, 1 H), 8.18 - 8.31 (m, 3 H), 7.95 (ddd, J=5.6, 3.4, 2.2 Hz, 2 H), 7.20 - 7.32 (m, 2 H), 6.80 - 6.97 (m, 2 H), 4.45 (d, J=5.7 Hz, 2 H), 3.72 (s, 3 H); LCMS RT = 5.99 min, m/z 372.0 [M+H+]
  • 18
  • [ 20332-16-5 ]
  • [ 2393-23-9 ]
  • [ 122-51-0 ]
  • [1,3]dioxolo[4,5-g]-7-(4-methoxyphenylmethyl)quinazolin-8(7H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
65.2% In ethanol;Reflux; Inert atmosphere; General procedure: The mixture containing substituted 2-aminobenzoic acid (0.71 mmol), substituted benzylamine (0.71 mmol), triethyl orthoformate (0.3 ml, 1.70mmol) and anhydrous ethanol (15 ml) was refluxed under N2 atmosphere for 2-8 h, cooled to room temperature and stood overnight. The precipitate was filtered, washed with ethanol, dried and recrystallized from ethanol to give the white or light yellow solid.
  • 19
  • [ 27421-51-8 ]
  • [ 381-98-6 ]
  • [ 119072-55-8 ]
  • [ 2393-23-9 ]
  • N-(2-(tert-butylamino)-1-(1-methyl-1H-indol-2-yl)-2-oxoethyl)-N-(4-methoxybenzyl)-2-(trifluoromethyl)acrylamide [ No CAS ]
  • 20
  • [ 422-64-0 ]
  • [ 2393-23-9 ]
  • C11H10F5NO2 [ No CAS ]
  • 21
  • [ 871836-51-0 ]
  • [ 2393-23-9 ]
  • N-(4-methoxybenzyl)-1H-pyrazolo[4,3-c]pyridin-4-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
525 mg at 150℃; for 6h; To <strong>[871836-51-0]4-chloro-1H-pyrazolo[4,3-c]pyridine</strong> (1.3 g, 8.46 mmol) was added (4- methoxyphenyl) methanamine (5 mL) and the resultant reaction mixture was heated in a closed reaction vessel at 150 °C for 6 h. The reaction was monitored by TLC. After completion of reaction, the reaction mixture was diluted with EtOAc (500 mL). The organic layer was washed with saturated NH4C1 solution (12x50 mL), water (2x200 mL), brine (150 mL), dried over Na2SO4 and concentrated. The crude compound was purified by silica-gel (100-200) column chromatography, compound eluting at 40percent EtOAc/hexane to afford N-(4- methoxybenzyl)- 1H-pyrazolo[4,3-c]pyridin-4-amine (525 mg) as a light brown solid.
  • 22
  • [ 6214-65-9 ]
  • [ 2393-23-9 ]
  • 5-(1-(4-methoxybenzyl)-1H-1,2,3-triazol-5-yl)pyrimidine-2,4-(1H,3H)-dione [ No CAS ]
  • 23
  • [ 2393-23-9 ]
  • [ 1180-71-8 ]
  • 2-((1S,3aS,4aR,4bR,9aR,11aS)-1-(furan-3-yl)-9a-(hydroxymethyl)-4b,7,7,11a-tetramethyl-3,5-dioxotetradecahydroisobenzofuro[5,4-f]oxireno[2,3-d]isochromen-9-yl)-N-(4-methoxybenzyl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With montmorillonite K-10; In ethanol; at 80℃; for 0.5h;Sealed tube; Microwave irradiation; General procedure: To a solution of 1 (2.0 mmol) in absolute EtOH (8.0 mL)in a glass tube was added dropwise the appropriate amine(3.6 mmol) and K-10 (0.3 g mmol-1); the quartz tubewas sealed with reaction mixture and introduced intoa microwave oven. The flask was irradiated for 30 min(150 W) the temperature of 80 C. After completion of thereaction the mixture was filtered, the organic phase wasdried with Na2SO4, filtered and the solvent was evaporatedunder reduced pressure to give the crude products. All thecompounds were purified by column chromatographyon silica gel using 2-5% EtOH-CH2Cl2 as eluent to giveanalytically pure products 3a-m. The products werecharacterized by corresponding spectroscopic data (1H and13C NMR, and HRMS).
  • 24
  • [ 22123-14-4 ]
  • [ 2393-23-9 ]
  • N-(4-methoxybenzyl)-6-methyl-4-(trifluoromethyl)pyridin-2-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
16.2% at 160℃; for 2h;Microwave irradiation; The 2-chloro-6-methyl-4 - (trifluoromethyl) pyridine (6.1g, 31 . 2mmol) adding microwave tube, add 4- methoxy animal pen amine (4.28g, 31 . 2mmol), 160 C microwave reaction 2 hours, the crude product by silica gel column chromatography (petroleum ether: ethyl acetate = 10:1) purified, to get the yellow solid title compound (1.5g, yield 16.2%).
  • 25
  • [ 1206972-45-3 ]
  • [ 2393-23-9 ]
  • N-(4-methoxybenzyl)-5-(trifluoromethoxy)pyridin-2-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
40% With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 160℃; for 2h;Microwave irradiation; A mixture of <strong>[1206972-45-3]2-chloro-5-(trifluoromethoxy)pyridine</strong> (0.99 g, 5 mmol), 4-methoxybenzylamine (2.6 mL, 20 mmol), DIEA (1.3 mL, 7.5 mmol), K2003 (1.0 g, 7.5 mmol) and DMF (13 mL) was stirred at 160 oC (microwave) for 2 hrs. The reaction mixture was concentrated under reduced pressure. The residue was dissolved in DCM (100 mL) and H20 (25 mL). The organic layer was separated (phase separating cartridge) and the solvent was removed under reduced pressure. The crude product was purified by column chromatography (Biotage SNAP 50 g column, 0 to 15% EtOAc/isohexane). The product was triturated with Et20 to give the title compound as a yellow oil(0.33 g, 40%).1H NMR (ppm)(400 MHz, CDCI3): 3.80 (3H, s), 4.42 (2H, d, J=5.8 Hz), 4.91 (IH, s), 6.35 (IH, d, J8.8 Hz), 6.90 - 6.87 (2H, m), 7.25 - 7.28 (3H, m), 8.04 (1 H, d, J=2.8 Hz)
  • 26
  • [ 37585-16-3 ]
  • [ 2393-23-9 ]
  • 7-chloro-2-(4-methoxyphenyl)quinazoline [ No CAS ]
  • (E)-4-chloro-2-((4-methoxybenzylidene)amino)benzaldehyde [ No CAS ]
  • 27
  • [ 50-00-0 ]
  • [ 1198-14-7 ]
  • [ 2393-23-9 ]
  • 5-bromo-7-(((4-methoxybenzyl)amino)methyl)quinolin-8-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
27% The solution of 4-methoxybenzylamine (211 muIota_, 0.226 g, 1.65 mmol) in ethanol (4 mL) was added 37percent formaldehyde (62 muIota_, 0.049 g, 1.65 mmol). The mixture was stirred for 1 hour. Then the solution of <strong>[1198-14-7]5-bromoquinolin-8-ol</strong> (0.336 g, 1.5 mmol) in ethanol (5 mL) was added to the reaction mixture. After that the mixture was refluxed at 50°C for 72 hours. The reaction mixture was allowed to cool down and the obtained precipitate was filtered off, washed with ethanol and crystallized from ethanol to give the titled compound (0.150 g, 27percent) as yellow crystals. Mp. 129-132 °C. 1 H NMR (300 MHz, CDCI3): delta 3.81 (d, 5H), 4.12 (s, 2H), 6.87 (d, 2H), 7.28 (d, 2H), 7.46-7.51 (m, 1 H), 7.62 (s, 1 H), 8.40 (d, 1 H), 8.83 (d, 1 H). 13C NMR (75 MHz, CDCI3): delta 49.4, 52.3, 55.2, 109.4, 1 13.9, 120.9, 122.3, 127.0, 129.6, 131.2, 134.9, 135.3, 139.6, 149.0, 152.0, 158.9. LCMS RT= 4.19 min. ESI+ m/z: 375.6 [M+H+].
  • 28
  • [ 201230-82-2 ]
  • [ 2393-23-9 ]
  • [ 22246-66-8 ]
  • 29
  • [ 2393-23-9 ]
  • [ 50607-30-2 ]
  • C13H18N2O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
61% To a stirred solution of 15-1 (2.0 g, 17.6 mmol) in DCE (50.0 mL) was added 15-2 (2.29mL, 17.6 mmol) and Acetic acid (1 mL, 17.6 mmol) and the reaction mixture was stirred for 1hour. Sodium cyanoborohydride (1.65 g, 26.4 mmol) was then added and the reaction mixture wasstirred at room temperature for 16 hours. It was diluted with 20percent IP A/DCM and organic layer was5 washed with saturated aqueous NaHC03 solution, water, dried over sodium sulfate andconcentrated. Crude material was purified by column chromatography (silica, gradient, 0percent-2.5percentMethnol in DCM) to afford 15-3 as Light yellow gummy solid. Yield-61 percent; LC MS: ES+ 23 5 .2.
  • 30
  • [ 4481-28-1 ]
  • [ 2393-23-9 ]
  • 1-N-[(4-methoxyphenyl)methyl]benzene-1,3-dicarboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
28% General procedure: A solution of 24 (1.0 equiv.), HOBt (1.1 equiv.) and EDC (1.5 equiv.) in DMF (1.3 mmol/mL) was stirred at rt for 15 minutes. The appropriate amine (2.0 equiv.) was added and the resulting solution was stirred at rt for 5 hours. Reaction media was diluted with water and aqueous phase was extracted 3 times with EtOAc. Combined organic layers were washed successively with a solution of HCl 1N, a saturated solution of NaHCO3 and brine, dried over Na2SO4 and concentrated. The resulting solid was then purified by column chromatography on silica gel using the appropriate heptanes:EtOAc mixture.
  • 31
  • [ 2393-23-9 ]
  • [ 1569-16-0 ]
  • 9-(4-methoxyphenyl)imidazo[1,5-a][1,8]naphthyridine [ No CAS ]
  • 32
  • [ 2393-23-9 ]
  • [ 1569-16-0 ]
  • 7-bromo-9-(4-methoxyphenyl)imidazo[1,5-a][1,8]naphthyridine [ No CAS ]
  • 33
  • [ 2393-23-9 ]
  • [ 65202-50-8 ]
  • methyl 6-(4-methoxybenzylamino)pyridazine-3-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate; In acetonitrile; at 80℃; for 16h; To a solution of (4-methoxyphenyl)methanamine (19.9 g, 145 mmol) in acetonitrile (150 ml_) at room temperature was added potassium carbonate (20.0 g, 145 mmol) and <strong>[65202-50-8]methyl 6-chloropyridazine-3-carboxylate</strong> (12.5 g, 72.4 mmol). The reaction mixture was stirred at 80 C for 16 h before it was cooled to room temperature and diluted with water (300 ml_). The aqueous layer was extracted with ethyl acetate (200 ml_ c 3). The combined organic layers were washed with brine, dried over sodium sulfate, filtered and concentrated. The crude residue was purified by column chromatography (silica gel, ethyl acetate/petroleum ether =1/3) to afford methyl 6-(4-methoxybenzylamino)pyridazine-3-carboxylate (28.0 g, crude) as a light yellow oil. (LCMS (ESI) m/z: 274.1 [M+H]+. Used in the next step directly without additional purification.
  • 35
  • [ 2393-23-9 ]
  • [ 61173-96-4 ]
 

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