4385-77-7|3-Pyridin-3-yl-benzoic acid| Ambeed

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Quality Control of [ 4385-77-7 ] Purity: 97% SDS Specification

COA

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NMR

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Product Details of [ 4385-77-7 ]

CAS No. :	4385-77-7
Formula :	C₁₂H₉NO₂
M.W :	199.21
SMILES Code :	OC(=O)C1=CC=CC(=C1)C1=CC=CN=C1
MDL No. :	MFCD03426512
InChI Key :	PXASTGBSGPFLFJ-UHFFFAOYSA-N
Pubchem ID :	2795575

Safety of [ 4385-77-7 ]

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

Computational Chemistry of [ 4385-77-7 ] 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.	1.54
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	2.0
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	1.99

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.8
Solubility	0.319 mg/ml ; 0.0016 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.	-2.68
Solubility	0.416 mg/ml ; 0.00209 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.	-6.1 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)	1.95

Application In Synthesis of [ 4385-77-7 ]

* 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 [ 4385-77-7 ]

[ 4385-77-7 ] Synthesis Path-Downstream 1~35

1
[ 67-56-1 ]
[ 4385-77-7 ]
[ 79601-27-7 ]

References: [1]Journal of Medicinal Chemistry,1981,vol. 24,p. 1475 - 1482.

2
[ 4385-67-5 ]
[ 4385-77-7 ]

References: [1]Journal of Medicinal Chemistry,1981,vol. 24,p. 1475 - 1482.

3
[ 626-55-1 ]
[ 25487-66-5 ]
[ 4385-77-7 ]

Yield	Reaction Conditions	Operation in experiment
83%	With potassium carbonate;bis-triphenylphosphine-palladium(II) chloride; In water; acetonitrile;Reflux;	Example 163 A3-(pyridin-3-yl)benzoic acid; To a solution of 3-boronobenzoic acid (1.5 g, 9 mmol) and 3-bromopyridine (1.5 g, 9.9 mmol) in acetonitrile (40 mL) and water (40 mL), potassium carbonate (5.5 g, 40 mmol), Bis(triphenylphosphine)palladium(II) chloride (400 mg, 0.37 mmol) was added. The mixture was stirred under reflux overnight. Then the hot suspension was filtered and concentrated to half of the original volume and washed with dichloromethane. The aquatic phase was adjusted to pH=3 with hydrochloric acid (1 M) and filtrated, washed with water. The residue was dried in vacuum to obtain 1.5 g of 3-(pyridin-3-yl)benzoic acid. Yield: 83%. LC-MS (ESI) m/z: 200 (M+1)+.
	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In acetonitrile; at 90℃; for 14.0h;	20 ml of 0.4 M sodium carbonate aqueous solution,3.2 g of 3-bromopyridine (21), 3.3 g of 3-carboxyphenylboronic acid and 1.15 g of tetrakis (triphenylphosphine) palladium (0) were added to 100 ml of acetonitrile,And the mixture was stirred at 90 C. for 14 hours. After completion of the reaction,Filter through Celite, add 1N dilute hydrochloric acid to the filtrate, Extracted with ethyl acetate, and washed with saturated brine.The organic layer was dried over anhydrous magnesium sulfate,The solvent was distilled off under reduced pressure.The precipitated crystals were washed with hexane and filtered,3- (Pyridin-3-yl) benzoic acid (22)Was obtained. To the solid,50 ml of ethanol and 5 ml of concentrated sulfuric acid were added.After heating under reflux for 12 hours,Sodium bicarbonate was added to the reaction solution to quench. After distilling off ethanol under reduced pressure,An aqueous sodium hydrogen carbonate solution was addedAnd extracted three times with ethyl acetate. The organic layers were combined,Washed with saturated brine,After drying with anhydrous magnesium sulfate,The solvent was distilled off under reduced pressure.The residue was purified by silica gel column chromatography (n-hexane: ethyl acetate = 4: 1)Ethyl 3- (pyridin-3-yl) benzoate(23) was obtained

References: [1]Synlett,2000,p. 829 - 831.
[2]Patent: US2009/197863,2009,A1 .Location in patent: Page/Page column 76.
[3]Journal of the American Chemical Society,2013,vol. 135,p. 1853 - 1863.
[4]Patent: JP5743418,2015,B2 .Location in patent: Paragraph 0142; 0143; 0144.

4
[ 626-55-1 ]
[ 4385-77-7 ]

References: [1]Journal of Medicinal Chemistry,1981,vol. 24,p. 1475 - 1482.

5
[ 4385-77-7 ]
[ 79412-84-3 ]

References: [1]Journal of Medicinal Chemistry,1981,vol. 24,p. 1475 - 1482.

6
[ 4385-77-7 ]
[ 79601-28-8 ]

References: [1]Journal of Medicinal Chemistry,1981,vol. 24,p. 1475 - 1482.

7
[ 4385-77-7 ]
[ 79412-67-2 ]

References: [1]Journal of Medicinal Chemistry,1981,vol. 24,p. 1475 - 1482.

8
[ 4385-77-7 ]
[ 79412-82-1 ]

References: [1]Journal of Medicinal Chemistry,1981,vol. 24,p. 1475 - 1482.

9
[ 4385-77-7 ]
3-(1-Propionyl-piperidin-3-yl)-benzoyl azide [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1981,vol. 24,p. 1475 - 1482.

10
[ 4385-77-7 ]
C₁₈H₂₃NO₅ [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1981,vol. 24,p. 1475 - 1482.

11
[ 4385-77-7 ]
[ 79412-83-2 ]

References: [1]Journal of Medicinal Chemistry,1981,vol. 24,p. 1475 - 1482.

12
[ 4385-77-7 ]
[ 79412-56-9 ]

References: [1]Journal of Medicinal Chemistry,1981,vol. 24,p. 1475 - 1482.

13
[ 4385-77-7 ]
[ 79412-68-3 ]

References: [1]Journal of Medicinal Chemistry,1981,vol. 24,p. 1475 - 1482.

14
[ 4385-77-7 ]
3-(1-Propyl-piperidin-3-yl)-benzoyl chloride; hydrochloride [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1981,vol. 24,p. 1475 - 1482.

15
[ 4385-77-7 ]
[ 79601-43-7 ]

References: [1]Journal of Medicinal Chemistry,1981,vol. 24,p. 1475 - 1482.

16
[ 4385-77-7 ]
[ 79412-81-0 ]

References: [1]Journal of Medicinal Chemistry,1981,vol. 24,p. 1475 - 1482.

17
[ 4385-77-7 ]
[ 343966-00-7 ]

References: [1]Journal of Medicinal Chemistry,1981,vol. 24,p. 1475 - 1482.

18
[ 4385-77-7 ]
[ 150336-90-6 ]

References: [1]Journal of Medicinal Chemistry,1981,vol. 24,p. 1475 - 1482.

19
[ 4385-77-7 ]
[ 146820-21-5 ]

References: [1]Journal of Medicinal Chemistry,1981,vol. 24,p. 1475 - 1482.

20
[ 28987-79-3 ]
[ 4385-77-7 ]

References: [1]Journal of Medicinal Chemistry,1981,vol. 24,p. 1475 - 1482.

21
[ 865314-31-4 ]
[ 4385-77-7 ]
N-[3'-(1-piperazinylmethyl)-3-biphenylyl]methyl}-3-(3-pyridinyl)benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃; for 16.0h;	A mixture of PyBOP (0.08 mmol in 200 ml_ of DMF), [3'-(1 - piperazinylmethyl)-3-biphenylyl]methyl}amine (44 Dmol in 200 mL of DMF) and DIPEA (30 mL) were added to <strong>[4385-77-7]3-(3-pyridinyl)benzoic acid</strong> (0.07 mmol). The resulting mixture was stirred for 16 hours at room temperature, then the solvent was removed under vacuum. The residue was redissolved in methanol and purified by loading onto a SPE cartridge (SCX, 500 mg), washing with MeOH, and eluting with a 2 M solution of NH3 in MeOH. The NH3 fraction was collected and evaporated under vacuum to give a gum which was redissolved in 1 :1 CHCI3 / TFA (0.5 mL). After stirring for 2 hours, the solvent was removed under vacuum and the residue was purified by MDAP to give the desired compound as a TFA salt. The free base of the compound was obtained by loading the salt onto a SPE cartridge (SCX, 500 mg), washing with MeOH, and eluting with 2 M NH3ZMeOH. The ammonia fraction was collected and the solvent was removed under vacuum to give the title compound (14 mg). LC/MS: m/z, 463 (M+H), 2.32 min.

References: [1]Patent: WO2006/55553,2006,A2 .Location in patent: Page/Page column 52.

22
[ 4385-77-7 ]
[ 1044873-05-3 ]

Yield	Reaction Conditions	Operation in experiment
	With oxalyl dichloride;N,N-dimethyl-formamide; In dichloromethane; at 0 - 20℃; for 3.5h;	EXAMPLE 5; (S)-8-cyano-15-methyl-N-[3-(3-pyridin-3-ylphenyl)-1H-1,2,4-triazol-5- yl]tetracyclo[6.6.2.02'7.09'14]hexadeca-2,4,6,9,11,13-hexaene-15-carboxamide EPO <DP n="61"/>; Step a; methyl 3-(pyridin-3-yI)benzoate; [00191] To a suspension of <strong>[4385-77-7]3-(pyridin-3-yl)benzoic acid</strong> (0.8 g, 4 mmol) and N,N- dimethylfo?nide (2 drops) in anhydrous methylene chloride (30 mL) was added oxalyl chloride (0.42 mL, 4.8 mmol) dropwise at 0C under argon. The mixture was stirred at RT for 3.5 hr and then concentrated. The yellow solid obtained was dissolved in anhydrous methanol (20 mL) at 0C. After stirring at RT for 30 min, the mixture was concentrated. The residue was dissolved in ethyl acetate, washed with saturated aqueous sodium bicarbonate solution, brine, and dried over anhydrous sodium sulfate. Concentration gave 0.84 g (99% yield) of methyl 3-(pyridin-3- yl)benzoate as a yellow solid. (M+H)+ = 214.16.
	With thionyl chloride;N,N-dimethyl-formamide; for 17.0h;Heating / reflux;	N-(3-Pyrid-3-ylbenzoyl)-6,7-dihydroxy-l,2,3,4-tetrahydroisoquinoline (Id)3-Pyrid-3-ylbenzoic acid (100 mg, 0.502 mmol) was suspended in 3 triL thionyl chloride together with a catalytical amount of DMF and refluxed for 17 hours before evaporation. The remaining residue was dissolved in 5 mL DMF and 6,7- dihydroxy-l,2,3,4-tetrahydroisoquinoline hydrobromide (124 mg, 0.502 mmol) followed by Et3N (141 muL, 1.00 mmol) were added. The resulting mixture was stirred at room temperature for 3 hours and then diluted with 25 ml water followed by extraction with ethyl acetate (3*30mL). The combined organic phase was dried over MgSO4 and evaporated into a pale mass. Purification with flash chromatography (pet.ether/EtOAc 1/1 ? 1/5) yielded 67 mg (39%) of N-(3-pyrid-3-ylbenzoyl)-6,7-dihydroxy-l,2,3,4- tetrahydroisoquinoline as pale solids. 1H-NMR (CD3OD) rotameric mixture delta 8.83 (br s, IH), 8.53 (br s, IH), 8.10 (br t, IH), 7.79 (br d, IH), 7.72 (br d, IH), 7.60 (br t, IH), 7.55-7.45 (br m, 2H), 6.63-6.55 (ma+mi)(m, 2H), 6.32 (mi)(s, IH), 4.70 (ma)(s, 2H), 4.46 (mi)(s, 2H), 3.95-3.88 (mi)(br, 2H), 3.65-3.57 (ma)(br, 2H), 2.85-2.75 (mi)(br, 2H), 2.75-2.68 (ma)(br, 2H). TLC (EtOAc) Rf 0.45. HRMS (ESI) calc for C2IHi9N2O3 [M+H] 347.1396, found 347.1367.
	With thionyl chloride;Reflux;	Example 163 Bmethyl 2-hydroxy-3-(3-(pyridin-3-yl)benzamido)benzoate; Thionyl chloride (10 mL) was added to <strong>[4385-77-7]3-(pyridin-3-yl)benzoic acid</strong> (1.5 g, 7.5 mmol) and the mixture was stirred under reflux overnight. The solvent was evaporated under reduced pressure and the residue was dried in vacuum giving 1.5 g crude 3-(pyridin-3-yl)benzoyl chloride. To a solution of methyl 3-amino-2-hydroxybenzoate (950 mg, 5.8 mmol) and pyridine (480 mg, 6 mmol) in toluene (50 mL) was added 3-(pyridin-3-yl)benzoyl chloride (1.5 g, 7 mmol) portion-wise at 0 C. and then stirred at 70 C. for 4 h. The resulting mixture was extracted with ethyl acetate (100 mL×4), the organic phase was washed with water and saturated sodium bicarbonate, dried with anhydrous sodium sulfate and evaporated under reduced pressure to obtain methyl 2-hydroxy-3-(3-(pyridin-3-yl)benzamido)benzoate as a yellow solid (1.8 g, yield 85%). LC-MS (ESI) m/z: 349 (M+1)+.

References: [1]Patent: WO2006/76702,2006,A1 .Location in patent: Page/Page column 59-60.
[2]Patent: WO2008/95852,2008,A1 .Location in patent: Page/Page column 32.
[3]Patent: US2009/197863,2009,A1 .Location in patent: Page/Page column 76.
[4]Journal of the American Chemical Society,2013,vol. 135,p. 1853 - 1863.

23
[ 4385-77-7 ]
(3-(pyridin-3-yl)phenyl)methanol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
53%	With borane-THF; In tetrahydrofuran;Heating / reflux;	3- (3-PYRIDYL)-BENZYL alcohol 46. To a 100 ML recovery flask was added 3- (3- pyridyl) -benzoic acid 45 (2.00 g, 10.0 mmol, 1.0 eq. ) and THF (20 mL). The resulting suspension is stirred. BH3 (1.0 M in THF, 15 mL, 15 mmol, 1.5 eq. ) was added the resulting mixture was refluxed overnight. Incomplete reduction was observed by LC/MS. Additional BH3 (10 mL) was added and the mixture was refluxed for an additional 6 h. LC/MS indicates complete reduction of the benzoic acid. The reaction mixture was concentrated and diluted with EtOAc. The organic layer was washed with a succession of water, HC1, brine. The combined aqueous layers were extracted with EtOAc. The organic phases were dried over anhydrous NA2SO4, filtered, and concentrated to give a clear oil. The crude materal was purified via flash chromatography (40% to 60% ETOAC/HEX) to give a white solid (995 mg, 53%).

References: [1]Patent: WO2005/20921,2005,A2 .Location in patent: Page/Page column 102.

24
[ 1227075-78-6 ]
[ 4385-77-7 ]
[ 1185745-71-4 ]

References: [1]Chemical Communications,2009,p. 4097 - 4099.

25
manganese(II) chloride tetrahydrate [ No CAS ]
[ 4385-77-7 ]
Mn(4-pyrid-3-ylbenzoate)2 [ No CAS ]

References: [1]Zeitschrift fur Anorganische und Allgemeine Chemie,2010,vol. 636,p. 857 - 860.

26
cobalt(II) chloride hexahydrate [ No CAS ]
[ 4385-77-7 ]
Co₂(4-pyrid-3-ylbenzoate)4(H₂O) [ No CAS ]

References: [1]Zeitschrift fur Anorganische und Allgemeine Chemie,2010,vol. 636,p. 857 - 860.

27
[ 4385-77-7 ]
[ 1404361-90-5 ]

References: [1]Bioorganic and medicinal chemistry,2012,vol. 20,p. 6751 - 6757,7.
[2]Patent: WO2014/43608,2014,A2 .

28
[ 4385-77-7 ]
[ 1404361-91-6 ]

References: [1]Bioorganic and medicinal chemistry,2012,vol. 20,p. 6751 - 6757,7.
[2]Patent: WO2014/43608,2014,A2 .

29
[ 4385-77-7 ]
[ 1404361-92-7 ]

References: [1]Bioorganic and medicinal chemistry,2012,vol. 20,p. 6751 - 6757,7.
[2]Patent: WO2014/43608,2014,A2 .

30
[ 4385-77-7 ]
[ 1418132-07-6 ]

References: [1]Bioorganic and medicinal chemistry,2012,vol. 20,p. 6751 - 6757,7.
[2]Patent: WO2014/43608,2014,A2 .

31
[ 4385-77-7 ]
[ 1404361-93-8 ]

References: [1]Bioorganic and medicinal chemistry,2012,vol. 20,p. 6751 - 6757,7.
[2]Bioorganic and medicinal chemistry,2012,vol. 20,p. 6751 - 6757,7.
[3]Patent: WO2014/43608,2014,A2 .
[4]Patent: WO2014/43608,2014,A2 .

32
[ 1404361-96-1 ]
[ 4385-77-7 ]
[ 1200831-80-6 ]

Yield	Reaction Conditions	Operation in experiment
68%	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; for 24.0h;	The amine (120 mg, 0.48 mmol) was dissolved in anhydrous CH2C12 (4 mL) then 3- (31- pyridyl)benzoic acid (97 mg, 0.49 mmol), EDC (0.121 g, 0.64 mmol, 1.3 eq.), HOBt (86 mg, 0.64 mmol, 1.3 eq.) and N,N-diisopropyl-N-ethylamine (0.340 mL, 2.0 mmol, 4 eq.) were added sequentially. The mixture was stirred 24 hours at room temperature. Silica gel (~lg) was added and the mixture was concentrated to dryness under reduced pressure. Flash column chromatography (RediSepRf Si02 (24g), 2% MeOH in CH2C12) gave Tripos 8 as a white amorphous solid (143 nig, 68 %). 1H NMR (CDC13, 300 MHz): delta 8.86 (d, J - 2.1 Hz, 1H), 8.61 (dd, J - 1.5 Hz, 4.8 Hz, 1H), 8.08 (d, J = 2.1 Hz, 1H), 8.01 (s, 1H), 7.91 (dt, J = 2.1 Hz, 5.7 Hz, 1H), 7.83 (dd, J - 2.4 Hz, 8.7 Hz, 1H), 7.78 (d, J - 7.8 Hz, 1H), 7.70 (d, J - 7.8 Hz, 1H), 7.54 (t, J - 7.8 Hz, 1H), 7.38 (dd, J = 4,8 Hz, 7.8 Hz, 1H), 6.72 (d, J = 7.2 Hz, 1H), 6.32 (d, J = 8.1 Hz, 1H), 4.25 (d, J = 12.6 Hz, 2H), 3.83 (s, 2H), 2.99 (m, 2H), 2.85 (q, J = 7.2 Hz, 2H), 2.48 (s, 3H), 2.07 (m, 2H), 1.54 (m, 2H); 1.23 (t, J = 7.2 Hz, 3H). EIMS m/r. 430 ([M+H]+).

References: [1]Bioorganic and medicinal chemistry,2012,vol. 20,p. 6751 - 6757,7.
[2]Patent: WO2014/43608,2014,A2 .Location in patent: Page/Page column 54; 55.

33
[ 87120-72-7 ]
[ 4385-77-7 ]
[ 1404361-89-2 ]

Yield	Reaction Conditions	Operation in experiment
85%	With benzotriazol-1-ol; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane;	To a flask containing 6.4 g (32.1 mmol) of <strong>[4385-77-7]3-pyrid-3-ylbenzoic acid</strong> (Maybridge), 4.6 g (34 mmol) HOBt-hydrate, was added dry THF (40mL) and methylene chloride (400mL). To the heterogeneous mixture was added 6.88 g (33.4 mmol) Dicyclohexylcarbodiimide (DCC), followed by 6.75 g (33.7 mmol) of 4-Amino- 1-Boc-piperidine (Aldrich). The reaction mixture became nearly homogeneous before a fine white precipitate is observed. The reaction was followed by TLC (5%MeOH/CH2C12) until complete. Upon completion, the reaction mixture was filtered and the filtrate concentrated to dryness. The residue was triturated with hot EtOAc (180mL), filtered and the solids washed with cold EtOAc. The filtrate was then concentrated to dryness, and re-dissolved in 30-40mL CH2C12 before adding 21 g of Si02 and concentrating the mixture to dryness. The solids were eluted on 220 g of Si02 starting with 1 :1 Et0Ac/CH2C12 and increasing to 100% EtOAc. The desired fractions were combined, heptane was added, and the solution concentrated to give 10.4 g (85%) of the Boc-piperidine Amide A as a white solid. 'HNMR (300 MHz, CDC13) = 8.85 (s, 1H), 8.61 (dd, J-4.7, 3.1 Hz, 1H), 7.98 (s, 1H), 7.90 (m, 1H), 7.72 (m, 2H), 7.54 (t, J-8Hz, 1H), 7.38 (m, 1H), 6.17 (d, J=8 Hz, 1H), 4,14 (br m, 3H), 2.91 (t, J=7Hz, 2H), 2.05 (d, J=7Hz, 2H), 1.49 (s,9H). MS(ESI+) - 382 (M+l), 282 (M- Boc+1).

References: [1]Bioorganic and medicinal chemistry,2012,vol. 20,p. 6751 - 6757,7.
[2]Patent: WO2014/43608,2014,A2 .Location in patent: Page/Page column 47; 48.

34
[ 4385-77-7 ]
[ 1429436-05-4 ]

References: [1]Journal of the American Chemical Society,2013,vol. 135,p. 1853 - 1863.

35
zinc(II) nitrate hexahydrate [ No CAS ]
[ 4385-77-7 ]
Zn(3-pyrid-3-ylbenzoic acid)<SUB>2</SUB> [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	at 120℃; for 72.0h;	The mixture of Zn(NO3)2.6H2O (0.5 mmol, 0.149 g), and3 mL NMF in a 20 mL vial was heated to 120C for three days,and then cooled to room temperature. The colorless crystalswere obtained in pure phase, washed with water and ethanol,and dried at room temperature (Yield: 88%). Anal. Calcd. forC24 H16ZnN2O4: C, 62.42; H, 3.49; N, 6.07. Found: C, 62.50;H, 3.48; N,6.05. IR: 1601 m, 1547 m, 1439 m, 1337 s, 1272 m,772 m, 617 m.

References: [1]Synthesis and Reactivity in Inorganic, Metal-Organic, and Nano-Metal Chemistry,2014,vol. 44,p. 793 - 797.

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

Related Functional Groups of
[ 4385-77-7 ]

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Related Parent Nucleus of
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CAS No.: 4385-77-7

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