18698-99-2|2-(2-Cyanophenyl)acetic acid| Ambeed

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Quality Control of [ 18698-99-2 ] Purity: 97% SDS Specification

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Product Details of [ 18698-99-2 ]

CAS No. :	18698-99-2
Formula :	C₉H₇NO₂
M.W :	161.16
SMILES Code :	O=C(O)CC1=CC=CC=C1C#N
MDL No. :	MFCD01646238
InChI Key :	QLHZKPQKYARBGT-UHFFFAOYSA-N
Pubchem ID :	87755

Safety of [ 18698-99-2 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H332-H335
Precautionary Statements:	P261-P280-P305+P351+P338

Computational Chemistry of [ 18698-99-2 ] Show Less

Physicochemical Properties

Num. heavy atoms	12
Num. arom. heavy atoms	6
Fraction Csp3	0.11
Num. rotatable bonds	2
Num. H-bond acceptors	3.0
Num. H-bond donors	1.0
Molar Refractivity	42.7
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	61.09 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.26
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	1.12
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.19
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.	1.02
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	1.53
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.22

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-1.78
Solubility	2.66 mg/ml ; 0.0165 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.	-2.0
Solubility	1.63 mg/ml ; 0.0101 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	-2.25
Solubility	0.904 mg/ml ; 0.00561 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.	-6.49 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)	1.65

Application In Synthesis of [ 18698-99-2 ]

* 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 [ 18698-99-2 ]

[ 18698-99-2 ] Synthesis Path-Downstream 1~33

1
[ 186581-53-3 ]
[ 18698-99-2 ]
[ 20921-96-4 ]

References: [1]Journal of Organic Chemistry,1953,vol. 18,p. 30,33.

2
[ 3342-78-7 ]
[ 18698-99-2 ]

References: [1]Journal of Organic Chemistry,1953,vol. 18,p. 30,33.

3
[ 18698-99-2 ]
[ 55086-26-5 ]

References: [1]Archiv der Pharmazie,1988,vol. 321,p. 265 - 272.

4
[ 3342-78-7 ]
[ 151-50-8 ]
[ 18698-99-2 ]

References: [1]Archiv der Pharmazie,1988,vol. 321,p. 265 - 272.

5
[ 3759-28-2 ]
[ 18698-99-2 ]

References: [1]Chemical Communications,1997,p. 1041 - 1042.
[2]Journal of the Chemical Society. Perkin transactions I,1997,p. 3197 - 3204.

7
[ 18698-99-2 ]
[ 117197-16-7 ]

Yield	Reaction Conditions	Operation in experiment
69%		Compound V (5.00 g, 0.031 mol) was dissolved in dry dichloromethane (150 mL). Afterwards, oxalylchloride (5.25 mL, 0.062 mol) was added, followed by a catalytic amount of Nu,Nu-dimethylformamide (about 0.05 mL). The mixture was then stirred at room temperature under an inert atmosphere for 70 minutes and evaporated to dryness. The oily residue was dissolved in dry tetrahydrofuran (THF) (50 mL) and added to an aqueous ammonia (26percent, 100 mL) cooled in an ice-water bath. The mixture was stirred at 0-5 °C for 20 minutes and then additional 40 minutes at room temperature. After the reaction was completed, the mixture was poured into a separation funnel and extracted by EtOAc (2 x 250 mL). The combined organic extracts were washed with saturated NaHC03 solution (2 x 100 mL), dried over MgS04 and evaporated to dryness. The crude product was crystallized from z'PrOH/hexane to give the title compound as an off- white solid (3.41 g, 69percent).

References: [1]Patent: WO2015/13520,2015,A1 .Location in patent: Page/Page column 20-21.
[2]Archiv der Pharmazie,1988,vol. 321,p. 265 - 272.

8
[ 18698-99-2 ]
2-(2-Cyano-phenyl)-N,N-dimethyl-acetamide [ No CAS ]

References: [1]Archiv der Pharmazie,1988,vol. 321,p. 265 - 272.

9
1-chloro-3-hydroxyquinoline [ No CAS ]
[ 3740-52-1 ]
[ 18698-99-2 ]

Yield	Reaction Conditions	Operation in experiment
	palladium on charcoal; In aq.sodium hydroxide;	(2E/Z, 4E)-N-Isobutyl 3-methyl-12-(1-chloro-3-isoquinolinyloxy)dodeca-2,4-dienamide Starting from 1-chloro-3-hydroxyquinoline and using the modified Stage a of Example CII 2-Nitrophenylacetic acid (ex Aldrich) (18.1 g) dissolved in 0.1M.aq.sodium hydroxide (100 ml) was subjected to catalytic hydrogenation (at 30-40 psi) over 10percent palladium on charcoal (2 g) until uptake ceased. The resultant solution was subjected first to diazotisation and then reaction with sodium cyanide and cuprous cyanide according to Simchen and Hafner, Ann. Chem., 1974, 1802 to give crude 2-cyanophenylacetic acid (14.9 g).

References: [1]Patent: US5114940,1992,A .

10
[ 18698-99-2 ]
[ 62-53-3 ]
N-phenyl-2-(2-cyanophenyl)acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%		Compound V (50.0 g, 0.310 mol) was charged to a 1 L jacketed reactor and suspended in dry ethyl acetate (700 mL). Thionyl chloride (27.2 mL, 0.372 mol) was added in one portion and the mixture was then heated at 45 °C for 2 hours. The mixture was then concentrated at a temperature 40-50 °C and reduced pressure (50- 200 mbar) to a volume of approximately 600 mL. Afterwards, the residue was cooled to 0 °C , followed by addition of aniline (62.2 mL, 0.682 mol) dissolved in ethyl acetate (150 mL). The rate of the addition was controlled to keep the temperature of the reaction mixture below 25 °C. After the addition was finished, the mixture was stirred at room temperature for 30 minutes, followed by addition of 2.5percent aqueous NaCl (200 mL) and heating the obtained mixture to 40-45°C with stirring. When all of the solid material was dissolved, the water phase was separated. The solvent in the remaining phase was replaced by isopropanol (iPrOH) by adding and evaporating of iPrOH in several portions (4 x 100 mL), then the mixture was concentrated at 40- 45 °C under reduced pressure (50-200 mbar) to a volume of approximately 400 mL, followed by addition of water (200 mL). The mixture was cooled to 0 °C, stirred at the same temperature for 30 minutes and filtered. The obtained product was then washed with 50percent aqueous iPrOH (180 mL) and dried in an inert atmosphere at room temp overnight to give compound Ill-a as an off- white solid (67.1 g, yield 92percent>) with a HPLC purity of ~92percent>. The product was analyzed by PXRD, and the PXRD pattern is shown in Figure 4.

References: [1]Patent: WO2015/13520,2015,A1 .Location in patent: Page/Page column 20.

11
[ 18698-99-2 ]
[ 62-53-3 ]
[ 380917-97-5 ]

References: [1]Patent: WO2015/13520,2015,A1 .

12
[ 18698-99-2 ]
[ 380917-97-5 ]

References: [1]Patent: WO2015/13520,2015,A1 .

13
[ 18698-99-2 ]
[ 380917-96-4 ]

References: [1]Patent: WO2015/13520,2015,A1 .

14
[ 18698-99-2 ]
ethyl 3-(1,4-dimethyl-1H-benzo[d][1,2,3]triazol-5-yl)-3-(1,2,3,3a,4,8b-hexahydroindeno[1,2-b]pyrrol-7-yl)propanoate hydrochloride [ No CAS ]
3-{1-[2-(2-cyanophenyl)acetyl]-1H,2H,3H,3aH,4H,8bH-indeno[1,2-b]pyrrol-7-yl}-3-(1,4-dimethyl-1H-1,2,3-benzotriazol-5-yl)propanoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
55%		To a solution of ethyl 3-(1 ,4-dimethyl-1 H-benzo[d][1 ,2,3]triazol-5-yl)-3-(1 ,2,3,3a,4,8b- hexahydroindeno[1,2-b]pyrrol-7-yl)propanoate, hydrochloride (50 mg, 0.113 mmol) in DCM (2mL) was added <strong>[18698-99-2]2-(2-cyanophenyl)acetic acid</strong> (21.93 mg, 0.136 mmcl), TEA (0.063 mL, 0.454 mmcl) and then T3P (50percent wt in EtOAc) (0.101 mL, 0.170 mmcl). The resulting reaction mixture was stirred at ambient temperature for 30 mm. The reaction mixture was concentrated under reduced pressure and dissolved in methanol (2.000 mL) after which was added NaOH (3 N)(0.378 mL, 1.134 mmol). The resulting reaction mixture was heated with microwave at 100 C for 20 mm. The reaction mixture was acidified with HCI (3 N) to pH 34 then concentrated under reduced pressure, and purified with reverse phase HPLC to afford the desired product 3-(1 -(2- (2-cyanophenyl)acetyl)-1 ,2,3,3a,4,8b-hexahydroindeno[1 ,2-b]pyrrol-7-yl)-3-(1 ,4-dimethyl-1 Hbenzo[d][1 ,2,3]triazol-5-yl)propanoic acid (32.4 mg, 0.062 mmol, 55.0 percent yield). LC-MS m/z520.3 (M+H), 0.90 mm (ret. time).
55.0%		To a solution of ethyl 3-(1,4-dimethyl-1H-benzo[d][1,2,3]triazol-5-yl)-3-(1,2,3,3a,4,8b- hexahydroindeno[1,2-b]pyrrol-7-yl)propanoate, hydrochloride (50 mg, 0.113 mmol) in DCM (2 mL) was added <strong>[18698-99-2]2-(2-cyanophenyl)acetic acid</strong> (21.93 mg, 0.136 mmol), TEA (0.063 mL, 0.454 mmol) and then T3P (50percent wt in EtOAc) (0.101 mL, 0.170 mmol). The resulting reaction mixture was stirred at ambient temperature for 30 min. The reaction mixture was concentrated under reduced pressure and dissolved in methanol (2.000 mL) after which was added NaOH (3 N) (0.378 mL, 1.134 mmol). The resulting reaction mixture was heated with microwave at 100°C for 20 min. The reaction mixture was acidified with HCl (3 N) to pH 34 then concentrated under reduced pressure, and purified with reverse phase HPLC to afford the desired product 3-(1-(2- (2-cyanophenyl)acetyl)-1,2,3,3a,4,8b-hexahydroindeno[1,2-b]pyrrol-7-yl)-3-(1,4-dimethyl-1H- benzo[d][1,2,3]triazol-5-yl)propanoic acid (32.4 mg, 0.062 mmol, 55.0 percent yield). LC-MS m/z 520.3 (M+H)+, 0.90 min (ret. time).

References: [1]Patent: WO2016/203401,2016,A1 .Location in patent: Page/Page column 99; 100.
[2]Patent: WO2018/104766,2018,A1 .Location in patent: Page/Page column 99-100.

15
[ 18698-99-2 ]
[ 1395030-58-6 ]