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Chemical Structure| 1700-02-3 Chemical Structure| 1700-02-3

Structure of 1700-02-3

Chemical Structure| 1700-02-3

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Product Details of [ 1700-02-3 ]

CAS No. :1700-02-3
Formula : C9H5Cl2N3
M.W : 226.06
SMILES Code : ClC1=NC(C2=CC=CC=C2)=NC(Cl)=N1
MDL No. :MFCD00047340
InChI Key :AMEVJOWOWQPPJQ-UHFFFAOYSA-N
Pubchem ID :15549

Safety of [ 1700-02-3 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H332-H335
Precautionary Statements:P280-P305+P351+P338-P310

Computational Chemistry of [ 1700-02-3 ] Show Less

Physicochemical Properties

Num. heavy atoms 14
Num. arom. heavy atoms 12
Fraction Csp3 0.0
Num. rotatable bonds 1
Num. H-bond acceptors 3.0
Num. H-bond donors 0.0
Molar Refractivity 55.28
TPSA ?

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

38.67 ?2

Lipophilicity

Log Po/w (iLOGP)?

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

2.68
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

3.98
Log Po/w (WLOGP)?

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

2.85
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.

1.94
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

3.21
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

2.93

Water Solubility

Log S (ESOL):?

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

-4.32
Solubility 0.0109 mg/ml ; 0.0000482 mol/l
Class?

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

Moderately soluble
Log S (Ali)?

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

-4.49
Solubility 0.00726 mg/ml ; 0.0000321 mol/l
Class?

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

Moderately 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

-5.04
Solubility 0.00208 mg/ml ; 0.00000918 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.

-4.85 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<2.0
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)

1.68

Application In Synthesis of [ 1700-02-3 ]

* 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 [ 1700-02-3 ]

[ 1700-02-3 ] Synthesis Path-Downstream   1~7

  • 1
  • [ 1700-02-3 ]
  • [ 136-77-6 ]
  • [ 176843-67-7 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride;aluminium trichloride; In sulfolane; methanol; ligroin; water; EXAMPLE 62 2,4-Bis(2,4-dihydroxy-5-hexylphenyl)-6-phenyl-s-triazine To a 750 mL sulfonation flask equipped with a mechanical stirrer, condenser, dropping funnel and a nitrogen atmosphere are charged 34.0 g (150 mmol) of 2,4-dichloro-6-phenyl-s-triazine, 44.0 g (330 mmol) of aluminum chloride and 100 mL of ligroin (boiling range 110-140 C). To that suspension, 60 mL of sulfolane are added dropwise with stirring over a 15 minute period with the temperature rising to 50 C. A solution of 62.1 g (320 retool) of 4-hexylresorcinol in 60 mL of sulfolane is then added dropwise over a 15 minute period. The temperature rises to 60 C. and hydrogen chloride is evolved. The reaction mixture is heated to 80 C. for four hours. The lower layer of the two-phase mixture is poured into a solution of 50 mL of concentrated hydrochloric acid in 500 mL of methanol and 300 mL of water. The mixture is stirred at room temperature for 14 hours. The product obtained is suspended in 800 mL of water at 80 C. for 1 hour, is isolated by filtration and resuspended under the same conditions, finally isolated and dried at 85 C. under vacuum. The title compound is obtained as a crude orange product (77.0 g) and melts at 230-238 C. It can be used without further purification. 1 H nmr (DMSO-d6) spectrum is consistent with the desired product. Analysis: Calcd for C33 H39 N3 O4: C, 73.2; H, 7.3; N, 7.8. Found: C, 73.2; H, 7.3; N, 7.6.
With hydrogenchloride;aluminium trichloride; In sulfolane; methanol; ligroin; water; EXAMPLE 62 2,4-Bis(2,4-dihydroxy-5-hexylphenyl)-6-phenyl-s-triazine To a 750 mL sulfonation flask equipped with a mechanical stirrer, condenser, dropping funnel and a nitrogen atmosphere are charged 34.0 g (150 mmol) of 2,4-dichloro-6-phenyl-s-triazine, 44.0 g (330 mmol) of aluminum chloride and 100 mL of ligroin (boiling range 110-140 C.). To that suspension, 60 mL of sulfolane are added dropwise with stirring over a 15 minute period with the temperature rising to 50 C. A solution of 62.1 g (320 mmol) of 4-hexylresorcinol in 60 mL of sulfolane is then added dropwise over a 15 minute period. The temperature rises to 60 C. and hydrogen chloride is evolved. The reaction mixture is heated to 80 C. for four hours. The lower layer of the two-phase mixture is poured into a solution of 50 mL of concentrated hydrochloric acid in 500 mL of methanol and 300 mL of water. The mixture is stirred at room temperature for 14 hours. The product obtained is suspended in 800 mL of water at 80 C. for 1 hour, is isolated by filtration and resuspended under the same conditions, finally isolated and dried at 85 C. under vacuum. The title compound is obtained as a crude orange product (77.0 g) and melts at 230-238 C. It can be used without further purification. 1 H nmr (DMSO-d6) spectrum is consistent with the desired product. Analysis: Calcd for C33 H39 N3 O4: C, 73.2; H, 7.3; N, 7.8. Found: C, 73.2; H, 7.3; N, 7.6.
With hydrogenchloride;aluminium trichloride; In sulfolane; methanol; ligroin; water; Example 62 2,4-Bis(2,4-dihydroxy-5-hexylphenyl)-6-phenyl-s-triazine To a 750 mL sulfonation flask equipped with a mechanical stirrer, condenser, dropping funnel and a nitrogen atmosphere are charged 34.0 g (150 mmol) of 2,4-dichloro-6-phenyl-s-triazine, 44.0 g (330 mmol) of aluminum chloride and 100 mL of ligroin (boiling range 110-140 C.). To that suspension, 60 mL of sulfolane are added dropwise with stirring over a 15 minute period with the temperature rising to 50 C. A solution of 62.1 g (320 mmol) of 4-hexylresorcinol in 60 mL of sulfolane is then added dropwise over a 15 minute period. The temperature rises to 60 C. and hydrogen chloride is evolved. The reaction mixture is heated to 80 C. for four horns. The lower layer of the two-phase mixture is poured into a solution of 50 mL of concentrated hydrochloric acid in 500 mL of methanol and 300 mL of water. The mixture is stirred at room temperature for 14 hours. The product obtained is suspended in 800 mL of water at 80 C. for 1 hour, is isolated by filtration and resuspended under the same conditions, finally isolated and dried at 85 C. under vacuum. The title compound is obtained as a crude orange product (77.0 g) and melts at 230-238 C. It can be used without further purification. 1 H nmr (DMSO-d6) spectrum is consistent with the desired product. Analysis: Calcd for C33 H39 N3 O4: C, 73.2; H, 7.3; N, 7.8. Found: C, 73.2; H, 7.3; N, 7.6.
  • 2
  • [ 1700-02-3 ]
  • [ 1082549-89-0 ]
  • 9,9′,9″,9′′′-((6-phenyl-1,3,5-triazine-2,4-diyl)bis(benzene-5,3,1-triyl))tetrakis(9H-carbazole) [ No CAS ]
  • 3
  • [ 1700-02-3 ]
  • [ 654664-63-8 ]
  • 2-chloro-4-phenyl-6-benzophenanthrene-2-yl-[1,3,5]triazine [ No CAS ]
YieldReaction ConditionsOperation in experiment
57% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; for 16h;Reflux; Inert atmosphere; triphenylene-2-boronic acid (4.20g, 15.4mmol), 2,4-dichloro-6-phenyl-1,3,5-triazine (3.49g, 15.4mmol), and Pd(PPh3)4 ( 0.89 g,and 0.77 mmol) K2CO3 aqueous solution (23.2 ml of 2M, 46.3mmol) together, it was added to THF (200ml). The reaction mixture was thoroughly degassed and heated to reflux for 16 hours under nitrogen. After cooling to room temperature, the solid was collected by filtration, washed with THF and heptane, 2-chloro-4-phenyl-6- (triphenylene-2- yl) as a pale yellow solid 1,3,5-triazine It was obtained (3.7g, 57%). The product was used without further purification.
  • 4
  • [ 1700-02-3 ]
  • [ 1036378-83-2 ]
  • C45H31N3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
63% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; for 10h;Reflux; Inert atmosphere; 5.0 g (22.12 mmol) of Intermediate L-1 (2,4-dichloro-6-phenyl-s-triazine), 18.12 g (50.87 mmol) of L-5, 7.64 g (55.30 mmol) of potassium carbonate, 1.28 g (1.11 mmol) of Tetrakis (triphenyl phosphine) palladium (0) (PPh3) 4 was added to 100 mL of tetrahydrofuran and 30 mL of water, and the mixture was heated under reflux for 10 hours under a nitrogen stream. The resulting mixture was added to methanol (500 mL), and the crystallized solid was filtered, dissolved in monochlorobenzene, filtered through silica gel / celite, and an organic solvent was removed in an appropriate amount, followed by recrystallization from methanol to obtain Compound A-2 , 63% yield). The result of elemental analysis of the resulting compound A-2 is as follows.
63% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; at 80℃; for 10h;Inert atmosphere; Synthesis Example 63: Synthesis of Compound A-20 Intermediate I-43 (5.0 g, 22.12 mmol), Intermediate I-42 (18.12 g, 50.87 mmol), potassium carbonate (7.64 g, 55.30 mmol), and tetrakis(triphenyl phosphine) palladium (0) (1.28 g, 1.11 mmol) were added to tetrahydrofuran (THF, 100 mL) and water (30 mL) in a 250 mL flask and then, heated and refluxed under a nitrogen stream for 10 hours. The obtained mixture was added to methanol (500 mL) to crystallize a solid, and the solid was filtered, dissolved in monochlorobenzene, filtered with silica gel/Celite, and then, recrystallized with methanol after removing an appropriate amount of an organic solvent to obtain Compound A-20 (8.5 g, 63%). An elemental analysis of Compound A-20 was as follows. (0384) calcd. C45H31N3: C, 88.06; H, 5.09; N, 6.85. found: C, 88.16; H, 5.23; N, 6.63.
  • 5
  • [ 1700-02-3 ]
  • [ 1036378-83-2 ]
  • 2-([1,1′:3′,1″-terphenyl]-5′-yl)-4-chloro-6-phenyl-1,3,5-triazine [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; at 80℃; for 12h;Inert atmosphere; Synthesis Example 44: Synthesis of Intermediate I-44 Compound I-42 (50 g, 140 mmol) was dissolved in THF (1 L) under a nitrogen environment, Compound I-43 (31 g, 140 mmol) and tetrakis(triphenylphosphine)palladium (1.6 g, 1.4 mmol) were added thereto, and the mixture was stirred. Potassium carbonate saturated in water (48 g, 350 mmol) was added thereto, and the obtained mixture was heated and refluxed at 80 C. for 12 hours. When the reaction was complete, water was added to the reaction solution, and the mixture was extracted with dichloromethane (DCM) and then, filtered after removing moisture with anhydrous MgSO4 and concentrated under a reduced pressure. This obtained residue was separated and purified through flash column chromatography to obtain Compound I-44 (32 g and 70%). HRMS (70 eV, EI+): m/z calcd for C27H18ClN3: 419.1189. found: 419. Elemental Analysis: C, 77%; H, 4%
59% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water;Reflux; 2,4-dichloro-6-phenyl-1,3,5-Triazine 1eq (26.9g) and 1,3,2-Dioxaborolane, 4,4,5,5-tetramethyl-2-[1,1 ':3',1''-terphenyl]-5'-yl- 1.1eq(46.7g) was suspended in 350ml of THF and 170ml of distilled water, and then Pd(PPh3)4 0.05eq(6.8g) and potassium carbonate (K2CO3) 2eq (32.9g) was added and stirred under reflux. When the reaction was completed, the solvent was dried, dissolved in dichloromethane, dried over magnesium sulfate (MgSO4), filtered, and the filtrate was recrystallized from nucleic acid to obtain 29.7 g (Y=59%) of intermediate d-1.
  • 6
  • [ 1700-02-3 ]
  • [ 84-67-3 ]
  • C37H35N7 [ No CAS ]
YieldReaction ConditionsOperation in experiment
78.11% 1) Clean all the glass instruments to be used in the experiment, dry and reserve, and install a mechanical stirring rod.First added to the 250mL three-necked flask of the nitrogen protection device<strong>[84-67-3]4,4'-diamino-2,2'-dimethylbiphenyl</strong> (6.7933 g, 32.0 mmol),Catalyst (1.1437g sodium carbonate, 0.1270g sodium hydroxide)And 10 mL of a mixed organic solvent 1,4-dioxane and toluene (volume ratio of 3:1), and heated to reflux until the solid is dissolved to obtain a mixed solution;2) 2,4-Dichloro-6-phenyl-1,3,5-triazine (0.9000 g, 4.0 mmol)Dissolved in 20 mL of 1,4-dioxane, the solution was added to the reaction flask through a constant pressure dropping funnel, and then fully refluxed for 6 h to obtain a mixed reaction solution;3) The reaction solution was poured into 60 mL of ice water, and after standing for a while, the solution was layered, the upper layer was a clear solution, the lower layer was solid precipitated, and the solid was subjected to column chromatography purification to obtain a volume ratio of ethyl acetate. : V petroleum ether = 1:1 as eluent, 1.7953 g of the target product conjugated diamine monomer was obtained, and the yield was 78.11%.
  • 7
  • [ 1700-02-3 ]
  • [ 890042-13-4 ]
  • 2-chloro-4-phenyl-6-benzophenanthrene-2-yl-[1,3,5]triazine [ No CAS ]
YieldReaction ConditionsOperation in experiment
68% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; at 80℃; for 12h;Inert atmosphere; <strong>[890042-13-4]4,4,5,5-tetramethyl-2-(triphenylen-2-yl)-1,3,2-dioxaborolane</strong> (50 g, 141 mmol) was dissolved in 0.5 L of tetrahydrofuran (THF) under a nitrogen environment, and 2,4-dichloro-6-phenyl-1,3,5-triazine (47.9 g, 212 mmol) and tetrakis(triphenylphosphine)palladium (1.63 g, 1.41 mmol) were added thereto and then, stirred. Subsequently, potassium carbonate saturated in water (48.7 g, 353 mmol) was added thereto and then, heated and refluxed at 80 C. for 12 hours. When a reaction was complete, after adding water to the reaction solution, the mixture was extracted with dichloromethane (DCM), treated with anhydrous magnesium sulfate to remove moisture, filtered, and concentrated under a reduced pressure. This obtained residue was separated and purified through flash column chromatography to obtain Intermediate I-1 (40.1 g, 68%). (0147) HRMS (70 eV, EI+): m/z calcd for C27H16ClN3: 417.1033, found: 417. (0148) Elemental Analysis: C, 78%; H, 4%
65% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; at 80℃; for 8h;Inert atmosphere; Will be purchased from P&H Tech Co., Ltd. (http://www.phtech.co.kr/)<strong>[890042-13-4]4,4,5,5-tetramethyl-2-(triphenylene-2-yl)-1,3,2-dioxaborolane</strong> (100g, 282mmol) dissolved in 0.1L Tetrahydrofuran (THF) was added under nitrogen and purchased from Tokyo Chemical Industry Co. Ltd. (http://www.tcichemicals.com/)2,4-dichloro-6-phenyl-1,3,5-triazine (95.7g, 423mmol) and tetrakis(triphenylphosphine)palladium (2.72g, 2.86mmol), then stirred. Subsequently, a saturated aqueous solution of potassium carbonate (97.4 g, 705 mmol) was added thereto, and then heated to reflux at 80C for 8 hours. When the reaction was completed, water was added to the reaction solution, and the mixture was extracted with dichloromethane (DCM), treated with anhydrous magnesium sulfate to remove moisture, filtered, and concentrated under reduced pressure. The resulting residue was separated and purified by flash column chromatography to obtain Intermediate I-1 (76.6 g, 65%).
40.1 g With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; at 80℃; for 12h; Dissolve 4,4,5,5-tetramethyl-2-(triphenylene-2-yl)-1,3,2-dioxaborane (50g, 141mmol) in 0.5 of a 1L round bottom flask L tetrahydrofuran (THF), add 2,4-dichloro-6-phenyl-1,3,5-triazine (47.9g, 212mmol) and tetrakis(triphenylphosphine) palladium (1.63g, 1.41 mmol), and the resulting mixture was stirred. Subsequently, a saturated aqueous solution of potassium carbonate (48.7 g, 353 mmol) was added thereto, and the resulting mixture was heated and refluxed at 80C for 12 hours. When the reaction was completed, water was added to the reaction solution, and the resultant was extracted with dichloromethane (DCM), treated with anhydrous magnesium sulfate to remove moisture, filtered, and concentrated under reduced pressure. The residue obtained in this way was separated and purified by flash column chromatography to obtain 40.1 g of intermediate product C-1-4.
 

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Technical Information

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