4385-76-6|4-Pyridin-4-yl-benzoic acid| Ambeed

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Quality Control of [ 4385-76-6 ] Purity: 98% SDS Specification

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Product Details of [ 4385-76-6 ]

CAS No. :	4385-76-6
Formula :	C₁₂H₉NO₂
M.W :	199.21
SMILES Code :	N1=CC=C(C=C1)C2=CC=C(C(=O)O)C=C2
MDL No. :	MFCD04114574
InChI Key :	DZLGZIGLHCRIMF-UHFFFAOYSA-N
Pubchem ID :	1520811

Safety of [ 4385-76-6 ]

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

Computational Chemistry of [ 4385-76-6 ] Show Less

Physicochemical Properties

Num. heavy atoms	15
Num. arom. heavy atoms	12
Fraction Csp3	0.0
Num. rotatable bonds	2
Num. H-bond acceptors	3.0
Num. H-bond donors	1.0
Molar Refractivity	56.63
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	50.19 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.52
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	2.68
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.45
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.	1.61
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	2.37
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.12

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.22
Solubility	0.119 mg/ml ; 0.000598 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.	-3.39
Solubility	0.0819 mg/ml ; 0.000411 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	-3.92
Solubility	0.0239 mg/ml ; 0.00012 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.	-5.61 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.	0.56

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)	1.34

Application In Synthesis of [ 4385-76-6 ]

* 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 [ 4385-76-6 ]

[ 4385-76-6 ] Synthesis Path-Downstream 1~35

Yield	Reaction Conditions	Operation in experiment
		4-[Pyridin-4-yl]-Benzoic Acid To a suspension of 4-[pyridin-4-yl]-benzaldehyde (approx. 2.8 g, 15 mmol) (reference example 8a) in t-butanol (100 mL) was added 2-methy-but-2-ene (15 mL) followed by a solution comprised of NaClO2 (14.7 g, tech. grade) and NaH2PO4.H2O (14.7 g, 105 mmol) in H2O (100 mL). This mixture was stirred for 20 min then the precipitated solid filtered off. This solid was washed with water then set aside. The organic phase of the mother liquor was separated then washed with brine, dried over MgSO4 and concentrated to give a solid. This material was combined with the solid obtained by filtration and dried under vacuum to give 2.34 g of the title compound. 1H NMR (DMSO) d 7.77 (d, J=6 Hz, 2H), 7.93 (d, J=8 Hz, 2H), 8.06 (d, J=8 Hz, 2H), 8.70 (d, J=6 Hz, 2H). MS (EI) m/z 199 (M)+.
		The residue obtained by distilling off the solvent under reduced pressure was suspended in N,N-dimethylformamide (10 ml), followed by the addition of 4-(4-pyridyl)benzoic acid (420 mg) obtained in Referential Example 2 and N,N-dimethyl-4-aminopyridine (309 mg). Under ice cooling, 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (405 mg) was added and the resulting mixture was stirred at room temperature for 68 hours. After concentration, the residue was purified by chromatography on a silica gel column (dichloromethane:methanol=70:1). The colorless solid so obtained was recrystallized from a mixed solvent of ethyl acetate and hexane, followed by recrystallization from ethyl acetate to obtain colorless needle crystals (185 mg). To the filtrate, on the other hand, saturated hydrochloric acid-ethanol (4 ml) was added.
		In a similar manner to Example 4 except for the use of the resulting residue and 4-(4-pyridyl)benzoic acid as the raw materials, the reaction was conducted, whereby the title compound was obtained. 1H-NMR (DMSO-d6) delta: 1.70-2.10(2H,m), 3.00-3.65(4H,m), 3.75-3.90(1H,m), 7.50-8.40(13H,m), 8.95-9.05(2H,m). MS (FAB) m/z: 492 [(M+H)+, Cl35], 494 [(M+H)+, Cl37].

		The residue obtained by distilling off the solvent under reduced pressure was suspended in N,N-dimethylformamide (10 ml), followed by the addition of 4-(4-pyridyl)benzoic acid (420 mg) obtained in Referential Example 2 and N,N-dimethyl-4-aminopyridine (309 mg). Under ice cooling, 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (405 mg) was added and the resulting mixture was stirred at room temperature for 68 hours. After concentration, the residue was purified by chromatography on a silica gel column (dichloromethane: methanol = 70:1). The colorless solid so obtained was recrystallized from a mixed solvent of ethyl acetate and hexane, followed by recrystallization from ethyl acetate to obtain colorless needle crystals (185 mg). To the filtrate, on the other hand, saturated hydrochloric acid-ethanol (4 ml) was added.
		In the same manner as in Example A-4, a reaction was conducted using the resulting residue and 4-(4-pyridyl)benzoic acid as starting materials, whereby the title compound was obtained. 1H-NMR (DMSO-d6) delta: 1.70-2.10(2H,m), 3.00-3.65(4H,m), 3.75-3.90(1H,m), 7.50-8.40(13H,m), 8.95-9.05(2H,m). MS (FAB) m/z: 492 [(M+H)+, Cl35], 494 [(M+H)+, Cl37]. Elementary analysis for C26H22ClN3O3SHCl1.8H2O Calculated: C, 55.68; H, 4.78; N, 7.49; Cl, 12.64; S, 5.72. Found: C, 55.62; H, 4.94; N, 7.67; Cl, 12.76; S, 5.79.

2
[ 14047-29-1 ]
[ 19524-06-2 ]
[ 4385-76-6 ]

Yield	Reaction Conditions	Operation in experiment
	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In toluene; for 10h;	35.144 mmol of 4-bromopyridine hydrochloride, 35.144 mmol, were weighed separately4-carboxyphenylboronic acid and 10 mmol of sodium carbonate were added to a toluene solution, and 0.08 mmol was addedOf tetraprophenylphosphonium palladium, in the catalyst tetrasthenyl phosphorus palladium under the action,Reaction for 10 h to obtain a white intermediate.The intermediate product is dried,Adding thionyl chloride,inReflux at 80 ° C,After completion of the reaction, the excess solvent was evaporated to dryness to give a yellow solid.The yellow solid was mixed with 5-aminoisophthalic acid in DMF and reacted at room temperature for 3 h. The reaction solution was added to 500 mL of distilled water,Precipitation of a large number of solid, that is, H2PYBI ligand.

References: [1]Synlett,2000,p. 829 - 831.
[2]Patent: CN106008565,2016,A .Location in patent: Paragraph 0027; 0034; 0035.

3
[ 4385-76-6 ]
[ 193153-18-3 ]

Yield	Reaction Conditions	Operation in experiment
	With thionyl chloride; at 80℃;	35.144 mmol of 4-bromopyridine hydrochloride, 35.144 mmol, were weighed separately4-carboxyphenylboronic acid and 10 mmol of sodium carbonate were added to a toluene solution, and 0.08 mmol was addedOf tetraprophenylphosphonium palladium, in the catalyst tetrasthenyl phosphorus palladium under the action,Reaction for 10 h to obtain a white intermediate.The intermediate product is dried,Adding thionyl chloride,inReflux at 80 ° C,After completion of the reaction, the excess solvent was evaporated to dryness to give a yellow solid.The yellow solid was mixed with 5-aminoisophthalic acid in DMF and reacted at room temperature for 3 h. The reaction solution was added to 500 mL of distilled water,Precipitation of a large number of solid, that is, H2PYBI ligand.

References: [1]Journal of Medicinal Chemistry,2000,vol. 43,p. 2087 - 2092.
[2]Archiv der Pharmazie,2008,vol. 341,p. 478 - 484.
[3]Patent: CN106008565,2016,A .Location in patent: Paragraph 0034; 0035.
[4]Chemical Communications,2017,vol. 53,p. 12802 - 12805.
[5]Chemistry - An Asian Journal,2018,vol. 13,p. 1312 - 1317.

4
[ 4385-76-6 ]
[ 193152-96-4 ]
[ 193152-99-7 ]

Yield	Reaction Conditions	Operation in experiment
		Compound (III) was partitioned between dichloromethane and aqueous sodium carbonate. The organic phase (containing the free base of (III)) was washed with additional aqueous sodium carbonate and was distilled under reduced pressure and solvent exchanged with dimethylformamide (DMF). This solution was assayed for wt/wt content of (III). To a suspension of (IV) (1.0 equivalent vs. (III)) in DMF were added 2 equivalents of 4-methylmorpholine and 1.1 equivalents of O-Benztriazol-1-yl-N,N,N?,N?-tetramethyluronium tetrafluoroborate (TBTU). This mixture was stirred at ambient temperature until ester activation was complete (about 90 minutes). The DMF solution of Compound (III) (1 equivalent) was added and the resulting solution stirred overnight after which HPLC indicated that the reaction was complete. Water was added at 75° C. and the mixture was cooled to crystallize the product. The mixture was cooled to 5° C., filtered, and the filter cake was washed with water. The product was dried under reduced pressure at 70° C.

References: [1]Bioorganic and medicinal chemistry letters,2002,vol. 12,p. 1671 - 1674.
[2]Patent: US9492437,2016,B2 .Location in patent: Page/Page column 8; 9.

5
[ 619-58-9 ]
[ 1692-15-5 ]
[ 4385-76-6 ]

References: [1]Tetrahedron Letters,2003,vol. 44,p. 5095 - 5098.

6
[ 769-92-6 ]
[ 4385-76-6 ]
N-(4-tert-butyl-phenyl)-4-pyridin-4-yl-benzamide [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 631 - 634.

7
[ 99163-12-9 ]
[ 4385-76-6 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 631 - 634.

8
[ 259807-52-8 ]
[ 4385-76-6 ]
1-[(6-chlorobenzothiazol-2-yl)sulfonyl]-4-[4-(4-pyridyl)benzoyl]piperazine [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,2005,vol. 13,p. 3927 - 3954.

9
[ 259807-51-7 ]
[ 4385-76-6 ]
1-[(5-chlorobenzothiazol-2-yl)sulfonyl]-4-[4-(4-pyridyl)benzoyl]piperazine [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,2005,vol. 13,p. 3927 - 3954.

10
4-(6-chloro-benzo[b]thiophene-2-sulfonyl)-piperazine-1-carboxylic acid tert-butyl ester [ No CAS ]
[ 4385-76-6 ]
1-[(6-chlorobenzo[b]thien-2-yl)sulfonyl]-4-[4-(4-pyridyl)benzoyl]piperazine [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,2005,vol. 13,p. 3927 - 3954.

11
[ 216959-78-3 ]
[ 4385-76-6 ]
1-[(5-chlorobenzo[b]thien-2-yl)sulfonyl]-4-[4-(4-pyridyl)benzoyl]piperazine [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,2005,vol. 13,p. 3927 - 3954.

12
[ 859140-24-2 ]
[ 4385-76-6 ]
1-[[5⁽⁶⁾-chlorobenzoimidazol-2-yl]sulfonyl]-4-[4-(4-pyridyl)benzoyl]piperazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		A solution of 1-(5-chlorobenzimidazol-2-ylsulphonyl)-4-(t-butyloxycarbonyl)piperazine (860 mg, 2.15 mmol) in dichloromethane/methanol (15 ml of 1:1) was treated with an excess of hydrogen chloride gas as a saturated solution in ethyl acetate. After stirring for 4 hrs. the solvent was removed in vacuo and the residue dried under high vacuum. This was then suspended in DMF and treated sequentially with 4-(4-pyridyl)benzoic acid (428 mg, 2.15 mmol), triethylamine (0.6 ml, 4.3 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDAC, 495 mg, 2.68 mmol). After stirring overnight the solvent was removed in vacuo and the residue taken up in dichloromethane (50 ml). This was washed sequentially with water, saturated sodium bicarbonate solution, water and brine. Evaporation of the solvent gave a residue which was purified by chromatography (MPLC on Merck Art 9385 silica, gradient eluting with ethyl acetate containing 0-8.0percent methanol) to give 1-(5-chlorobenzimidazol-2-ylsulphonyl)-4-[4-(4-pyridyl)benzoyl]piperazine as colourless crystals (370 mg) from ethanol, m.p. 242-244° C., 1H NMR (d6DMSO) 3.0-3.4 ppm (broad s, 4H), 3.4-3.8 ppm (broad s, 4H), 7.4 ppm (d, 1H), 7.5 ppm (d, 2H), 7.6-7.8 ppm (m, 4H), 7.85 ppm 2H), 8.6 ppm (d, 2H), 14.0 ppm (broad s, 1H); MS (M+H)+ 482/484. [00116] The requisite 1-(5-chlorobenzimidazol-2-ylsulphonyl)-4-(t-butyloxycarbonyl)piperazine starting material was prepared as follows. A suspension of 5-chloro-2-thiolbenzimidazole (500 mg, 2.71 mmol) in acetic acid (2.5 ml) and water (10 ml) was cooled to 5° C. and chlorine gas bubbled in slowly, keeping the temperature below 7° C. The flow of chlorine was maintained until no more was absorbed, and then for a further 15 mins., after which time the reaction was purged with argon. The suspension was filtered off, washed quickly with water and then added in small portions to a stirred, cooled (5° C.) solution of N-Boc piperazine (1.26 g, 6.78 mmol) in dichloromethane (20 ml). After stirring for 1 hr. At ambient temperature, the reaction mixture was diluted with more dichloromethane (30 ml) and washed sequentially with citric acid solution (30 ml, 1M), sat. brine (30 ml), water (2.x.30 ml) and sat. brine (30 ml). The solution was dried (Phase-Sep paper) and evaporated to give 1-(5-chlorobenzimidazol-2-ylsulphonyl)4-(t-butyloxycarbonyl)piperazine as a brown foam (880 mg, 81percent yield), which was used without further purification; 1H NMR (CDCl3) 1.4 ppm (s, 9H), 3.4 ppm (m, 4H), 3.6 ppm (m, 4H), 7.4 ppm (d, 1H), 7.4-7.6 ppm (broad s, 1H), 7.7-7.9 ppm (broad s, 1H); MS (M+H)+ 401/403 (w), (M+H-56)+ 345/347 (s).

References: [1]Bioorganic and Medicinal Chemistry,2005,vol. 13,p. 3927 - 3954.
[2]Patent: US6753331,2004,B1 .Location in patent: Page column 15.

13
[ 259807-35-7 ]
[ 4385-76-6 ]
1-[(5-chloro-1-ethylindol-2-yl)sulfonyl]-4-[4-(4-pyridyl)benzoyl]piperazine [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,2005,vol. 13,p. 3927 - 3954.

14
[ 259807-33-5 ]
[ 4385-76-6 ]
[ 259802-91-0 ]

References: [1]Bioorganic and Medicinal Chemistry,2005,vol. 13,p. 3927 - 3954.

15
[ 4385-76-6 ]
[ 57260-71-6 ]
[ 222986-36-9 ]

References: [1]Bioorganic and Medicinal Chemistry,2005,vol. 13,p. 3927 - 3954.

16
[ 4423-10-3 ]
[ 4385-76-6 ]

Yield	Reaction Conditions	Operation in experiment
94 - 97%	With sulfuric acid; ozone; acetic acid;manganese(II) acetate; at 16℃; for 1h;	Example 11: 4-(4-Pyridyl)benzoic Acid In a 100 ml jacketed vessel, 200 ml of acetic acid, 0.05 g of manganese(II) acetate, 1.74 g of sulfuric acid and 3.0 g of 4-(p-tolyl)pyridine were initially charged. The mixture was cooled to 16° C. and 4.0 g of ozone were introduced within a period of 60 minutes. After completion of ozonolysis, the ozone present in the solvent was blown out using nitrogen. Analysis of the reaction mixture by means of HPLC or GC gave the following results: 4-(p-tolyl)pyridine: >0.1percent; 4-(4-pyridyl)benzoic acid: 94-97percent

References: [1]Patent: US2003/216577,2003,A1 .Location in patent: Page/Page column 5.
[2]Molecular Crystals and Liquid Crystals Science and Technology, Section A: Molecular Crystals and Liquid Crystals,2001,vol. 365,p. 75 - 79.

17
[ 4385-76-6 ]
4-(pyridin-4-yl)benzoyl chloride hydrochloride [ No CAS ]

References: [1]Journal of Organic Chemistry,2006,vol. 71,p. 4706 - 4709.

18
[ 925242-62-2 ]
[ 4385-76-6 ]
N-(6-dimethylaminomethyl-1,2,3,4-tetrahydro-naphthalen-2-yl)-N-methyl-4-pyridin-4-yl-benzamide [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 814 - 818.

19
[ 4385-76-6 ]
(+)-tert-butyl (2R,3R)-2-(3-cyanobenzyl)-3-(4-(pyridin-4-yl)benzamido)butanoate [ No CAS ]

References: [1]Journal of Organic Chemistry,2006,vol. 71,p. 4706 - 4709.

20
[ 4385-76-6 ]
1-[(6-chlorobenzo[b]furan-2-yl)sulfonyl]-4-[4-(4-pyridyl)benzoyl]piperazine [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,2005,vol. 13,p. 3927 - 3954.

21
[ 4385-76-6 ]
1-[(5-chlorobenzo[b]furan-2-yl)sulfonyl]-4-[4-(4-pyridyl)benzoyl]piperazine [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,2005,vol. 13,p. 3927 - 3954.

22
[ 4385-76-6 ]
[ 249292-06-6 ]

References: [1]Bioorganic and Medicinal Chemistry,2005,vol. 13,p. 3927 - 3954.

23
[ 4385-76-6 ]
[ 207798-71-8 ]

References: [1]Bioorganic and Medicinal Chemistry,2005,vol. 13,p. 3927 - 3954.

24
[ 4385-76-6 ]
4-[4-[[4-[(6-Chloroindol-2-yl)sulfonyl]piperazin-1-yl]carbonyl]phenyl]pyridine N-oxide [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,2005,vol. 13,p. 3927 - 3954.

25
[ 4385-76-6 ]
[ 859140-20-8 ]

References: [1]Bioorganic and Medicinal Chemistry,2005,vol. 13,p. 3927 - 3954.

26
[ 87199-17-5 ]
3-pyridyl halide [ No CAS ]
[ 4385-76-6 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 631 - 634.

27
[ 4385-76-6 ]
[ 193153-02-5 ]

References: [1]Bioorganic and medicinal chemistry letters,2002,vol. 12,p. 1671 - 1674.
[2]Patent: US9492437,2016,B2 .

28
[ 4385-76-6 ]
(2R,3R)-2-(3-Carbamimidoyl-benzyl)-3-(4-pyridin-4-yl-benzoylamino)-butyric acid methyl ester [ No CAS ]

References: [1]Bioorganic and medicinal chemistry letters,2002,vol. 12,p. 1671 - 1674.

29
[ 4385-76-6 ]
4-{4-[(1R,2R)-3-(3-Cyano-phenyl)-2-methoxycarbonyl-1-methyl-propylcarbamoyl]-phenyl}-1-methyl-pyridinium; iodide [ No CAS ]

References: [1]Bioorganic and medicinal chemistry letters,2002,vol. 12,p. 1671 - 1674.

30
[ 4385-76-6 ]
N₁-(4-Methoxybenzoyl)-N₂-[4-(4-pyridyl)benzoyl]-1,2-benzenediamine [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2000,vol. 43,p. 2087 - 2092.

31
[ 4385-72-2 ]
[ 4385-76-6 ]

References: [1]Patent: US6359134,2002,B1 .Location in patent: Referential example 25.

32
[ 4385-76-6 ]
[ 203521-17-9 ]
[ 207798-71-8 ]

References: [1]Patent: US6359134,2002,B1 .Location in patent: Example 47.

33
[ 207798-96-7 ]
[ 4385-76-6 ]
[ 207798-67-2 ]

References: [1]Patent: US6359134,2002,B1 .Location in patent: Example 59.

34
1-(4-vinylbenzenesulfonyl)piperazine [ No CAS ]
[ 4385-76-6 ]
1-[4-(4-pyridyl)benzoyl]-4-(p-styrenesulfonyl)piperazine [ No CAS ]

References: [1]Patent: US6359134,2002,B1 .Location in patent: Example 172.

35
[ 249292-34-0 ]
[ 4385-76-6 ]
[ 249292-02-2 ]

Yield	Reaction Conditions	Operation in experiment
	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In DMF (N,N-dimethyl-formamide);	A stirred suspension of 4-(4-pyridyl)benzoic acid (252 mg, 1.27 mmol) in dimethylformamide (10 ml) was treated sequentially with 1-(5-chloroindol-2-ylsulphonyl)piperazine (380 mg, 1.27 mmol), 1-hydroxybenzotriazole hydrate (HOBT, 271 mg, 1.77 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodi-imide hydrochloride (EDAC, 291 mg, 1.52 mmol). After stirring overnight the solvent was removed in vacuo and the residue taken up in dichloromethane (50 ml). This was washed sequentially with water, saturated sodium bicarbonate solution, water and brine. Evaporation of the solvent gave a residue which was chromatographed (MPLC on Merck Art 9385 silica, gradient eluting with dichloromethane containing 0-3.5% v/v of methanol) to yield, after crystallisation from acetone, 1-(5-chloroindol-2-ylsulphonyl)-4-[4-(4-pyridyl)benzoyl]piperazine as colourless crystals (244 mg), m.p. 185-188 C., 1H NMR (d6DMSO) 3.0-3.2 ppm (broad s, 4H), 3.4-3.8 ppm (broad s, 4H), 7.0 ppm (s, 1H), 7.3 ppm (dd, 1H), 7.5 ppm (m, 3H), 7.7 ppm (m, 2H), 7.8 ppm (m, 3H), 8.6 ppm (m, 2H), 12.4 ppm (broad s, 1H), the spectrum also contained a signal due to acetone, ca 0.5 mol. eq.; Microanalysis, found: C, 59.9; H, 4.4; N, 10.6; S, 6.1%; C24H21N4O3CIS. 0.5C3H6O requires: C, 60.1; H, 4.7; N, 11.0; S, 6.3%; MS (M+H)+ 481/483. [00105] The requisite 1-(5-chloroindol-2-ylsulphonyl)piperazine starting material was prepared as follows 1-(1-Benzenesulphonyl-5-chloroindol-2-ylsulphonyl)piperazine (4.15 g, 9.44 mmol) was treated with sodium hydroxide solution (32 ml of 2.5M), giving a yellow suspension. This was warmed to 80 C. with vigorous stirring and stirred for 45 mins, giving complete solution. The solution was cooled to ambient temperature and carefully treated with concentrated hydrochloric acid to pH 8; the resultant precipitate was filtered off, washed with water and dried to give 1-(5-chloroindol-2-ylsulphonyl)piperazine as a pale yellow solid, 1H NMR (d6DMSO) 2.75 ppm (m, 4H), 2.9 ppm (m, 4H), 7.0 ppm (s, 1H), 7.3 ppm (dd, 1H), 7.5 ppm (d, 1H), 7.8 ppm (d, 1H); MS (M+H)+ 300/302. [00106] The requisite 1-(1-benzenesulphonyl-5-chloroindol-2-ylsulphonyl)piperazine starting material was prepared as follows. A solution of 1-benzenesulphonyl-5-chloroindol-2-ylsulphonyl chloride (10.0 g, 25.6 mmol) in dichloromethane (100 ml) was added dropwise to a stirred solution of piperazine (13.23 g, 6 eq.) in dichloromethane (200 ml), and the mixture stirred for a further 2 hrs. The reaction mixture was then washed with water (3×200 ml), dried (Phase-Separating paper) and evaporated to give a red oil which was purified by flash chromatography using Merck silica (Art. 9385), eluting with dichloromethane containing methanol (0-6%), to give 1-(1-benzene sulphonyl-5-chloroindol-2-ylsulphonyl)piperazine as a colourless solid, 1H NMR (CDCl3) 2.95 ppm (m, 4H), 3.4 ppm (m, 4H), 7.4 ppm (m, 4H), 7.55 ppm (m, 2H), 8.0 ppm (d, 2H), 8.0 ppm (d, 1H); MS (M+H)+ 440/442. [00107] The requisite 1-benzene sulphonyl-5-chloroindol-2-ylsulphonyl chloride starting material may be prepared by a method analagous to that reported in J. Med. Chem. 33 749 (1990), starting from 5-chloroindole.

References: [1]Patent: US6753331,2004,B1 .Location in patent: Page column 12,13.

Historical Records

Technical Information

• Arndt-Eistert Homologation • Hunsdiecker-Borodin Reaction • Passerini Reaction • Preparation of Amines • Preparation of Carboxylic Acids • Reactions of Amines • Reactions of Benzene and Substituted Benzenes • Reactions of Carboxylic Acids • Schmidt Reaction • Specialized Acylation Reagents-Ketenes • Ugi Reaction

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[ 4385-76-6 ]

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Related Parent Nucleus of
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CAS No.: 4385-76-6

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