221615-75-4|1-(6-Methylpyridin-3-yl)-2-(4-(methylsulfonyl)phenyl)ethanone| Ambeed

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Quality Control of [ 221615-75-4 ] Purity: 97% SDS Specification

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Product Details of [ 221615-75-4 ]

CAS No. :	221615-75-4
Formula :	C₁₅H₁₅NO₃S
M.W :	289.35
SMILES Code :	O=S(C1=CC=C(CC(C2=CC=C(C)N=C2)=O)C=C1)(C)=O
MDL No. :	MFCD11110696
InChI Key :	YBFHILNBYXCJKD-UHFFFAOYSA-N
Pubchem ID :	9925991

Safety of [ 221615-75-4 ]

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

Computational Chemistry of [ 221615-75-4 ] Show Less

Physicochemical Properties

Num. heavy atoms	20
Num. arom. heavy atoms	12
Fraction Csp3	0.2
Num. rotatable bonds	4
Num. H-bond acceptors	4.0
Num. H-bond donors	0.0
Molar Refractivity	76.98
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	72.48 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.01
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	1.77
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	3.3
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.	1.39
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	3.01
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.3

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.93
Solubility	0.341 mg/ml ; 0.00118 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.	-2.91
Solubility	0.356 mg/ml ; 0.00123 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	-5.59
Solubility	0.000745 mg/ml ; 0.00000258 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.	-6.81 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<0.0
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)	2.19

Application In Synthesis of [ 221615-75-4 ]

* 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 [ 221615-75-4 ]

[ 221615-75-4 ] Synthesis Path-Downstream 1~35

1
[ 53014-84-9 ]
[ 221615-75-4 ]

References: [1]Journal of Organic Chemistry,2000,vol. 65,p. 8415 - 8420.

2
[ 5470-70-2 ]
[ 221615-75-4 ]

References: [1]Journal of Organic Chemistry,2000,vol. 65,p. 8415 - 8420.
[2]Journal of Organic Chemistry,2000,vol. 65,p. 8415 - 8420.
[3]Journal of Organic Chemistry,2000,vol. 65,p. 8415 - 8420.
[4]Patent: WO2012/66570,2012,A2 .
[5]Patent: US2013/245272,2013,A1 .

3
[ 221615-71-0 ]
[ 221615-75-4 ]

References: [1]Journal of Organic Chemistry,2000,vol. 65,p. 8415 - 8420.
[2]Journal of Organic Chemistry,2000,vol. 65,p. 8415 - 8420.
[3]Journal of Organic Chemistry,2000,vol. 65,p. 8415 - 8420.

4
[ 221615-75-4 ]
[ 202409-33-4 ]

References: [1]Journal of Organic Chemistry,2000,vol. 65,p. 8415 - 8420.
[2]Organic letters,2000,vol. 2,p. 2339 - 2341.
[3]Patent: WO2013/105106,2013,A1 .

5
[ 221615-75-4 ]
[ 325855-74-1 ]

References: [1]Organic Letters,2001,vol. 3,p. 209 - 211.

6
[ 221615-75-4 ]
(2Z,4Z)-4-Chloro-5-dimethylamino-2-(4-methanesulfonyl-phenyl)-1-(6-methyl-pyridin-3-yl)-penta-2,4-dien-1-one [ No CAS ]

References: [1]Journal of Organic Chemistry,2000,vol. 65,p. 8415 - 8420.

7
[1-(6-Methyl-pyridin-3-yl)-meth-(E)-ylidene]-phenyl-amine [ No CAS ]
[ 221615-75-4 ]

References: [1]Journal of Organic Chemistry,2000,vol. 65,p. 8415 - 8420.

8
C₅H₅NCH₂C(NC₂H₆O)2 [ No CAS ]
[ 221615-75-4 ]

References: [1]Journal of Organic Chemistry,2000,vol. 65,p. 8415 - 8420.

9
[ 307531-87-9 ]
[ 221615-75-4 ]

References: [1]Journal of Organic Chemistry,2000,vol. 65,p. 8415 - 8420.

10
[ 221615-75-4 ]
5-bromo-3-(4-methanesulfonyl-phenyl)-6'-methyl-[2,3']bipyridinyl [ No CAS ]

References: [1]Organic letters,2000,vol. 2,p. 2339 - 2341.

11
[ 221615-75-4 ]
5-iodo-3-(4-methanesulfonyl-phenyl)-6'-methyl-[2,3']bipyridinyl [ No CAS ]

References: [1]Organic letters,2000,vol. 2,p. 2339 - 2341.

12
[ 221615-75-4 ]
3-(4-methanesulfonyl-phenyl)-6'-methyl-5-nitro-[2,3']bipyridinyl [ No CAS ]

References: [1]Organic letters,2000,vol. 2,p. 2339 - 2341.

13
[ 221615-75-4 ]
(2Z,4Z)-4-Chloro-5-dimethylamino-2-(4-methanesulfonyl-phenyl)-1-(6-methyl-pyridin-3-yl)-penta-2,4-dien-1-one [ No CAS ]

References: [1]Organic letters,2000,vol. 2,p. 2339 - 2341.

14
[ 221615-75-4 ]
(2Z,4Z)-4-Bromo-5-dimethylamino-2-(4-methanesulfonyl-phenyl)-1-(6-methyl-pyridin-3-yl)-penta-2,4-dien-1-one [ No CAS ]

References: [1]Organic letters,2000,vol. 2,p. 2339 - 2341.

15
[ 221615-75-4 ]
(2Z,4Z)-5-Dimethylamino-4-iodo-2-(4-methanesulfonyl-phenyl)-1-(6-methyl-pyridin-3-yl)-penta-2,4-dien-1-one [ No CAS ]

References: [1]Organic letters,2000,vol. 2,p. 2339 - 2341.

16
[ 221615-75-4 ]
3-(4-methanesulfonyl-phenyl)-6'-methyl-5-trifluoromethyl-[2,3']bipyridinyl [ No CAS ]

References: [1]Organic letters,2000,vol. 2,p. 2339 - 2341.

17
[ 221615-75-4 ]
(2Z,4Z)-5-Dimethylamino-2-(4-methanesulfonyl-phenyl)-1-(6-methyl-pyridin-3-yl)-4-nitro-penta-2,4-dien-1-one [ No CAS ]

References: [1]Organic letters,2000,vol. 2,p. 2339 - 2341.

18
[ 221615-75-4 ]
(2Z,4Z)-5-Dimethylamino-2-(4-methanesulfonyl-phenyl)-1-(6-methyl-pyridin-3-yl)-4-trifluoromethyl-penta-2,4-dien-1-one [ No CAS ]

References: [1]Organic letters,2000,vol. 2,p. 2339 - 2341.

19
[ 221615-75-4 ]
2-[3-(4-methanesulfonyl-phenyl)-6'-methyl-[2,3']bipyridinyl-5-yl]-isoindole-1,3-dione [ No CAS ]

References: [1]Organic letters,2000,vol. 2,p. 2339 - 2341.

20
[ 221615-75-4 ]
2-[(Z)-1-[1-Dimethylamino-meth-(Z)-ylidene]-3-(4-methanesulfonyl-phenyl)-4-(6-methyl-pyridin-3-yl)-4-oxo-but-2-enyl]-isoindole-1,3-dione [ No CAS ]

References: [1]Organic letters,2000,vol. 2,p. 2339 - 2341.

21
[ 221615-75-4 ]
2-chloroaminoacrolein [ No CAS ]
[ 202409-33-4 ]

References: [1]Patent: US6369275,2002,B1 .Location in patent: Page column 12.

22
2-chloro-1,3-(bis-morpholinyl)trimethinium hexafluoro phosphate [ No CAS ]
[ 221615-75-4 ]
[ 202409-33-4 ]

Yield	Reaction Conditions	Operation in experiment
		Example-7; Preparation of Etoricoxib; Potassium tert. butoxide (1.4g) was dissolved in THF (7ml) and the solution was maintained at 25-30 0C for 10 minutes and then cooled to 10 0C. Subsequently, solution of l-(6-methylpyridin-3-yl)-2[4-(methylsulfonyl)rhohenyl] ethanone (5g) in THF was added and kept the mixture for lhr at 25-30 0C. Subsequently, 2-chloro 1,3 -(bis morpholinyl) trimethinium hexafluoro phosphate (4g) followed by THF (20ml) was added and the reaction mixture was maintained at 25-30 0C for 2 hrs. The reaction mixture was dumped in to the mixture of trifluoroacetic acid (0.6g), acetic acid (4.4g) and THF (10ml) and maintained the reaction mixture at 25-30 0C for 2 hrs. The reaction mixture was stirred at 55-60 0C for 3 hrs and aq. ammonia solution (30ml), and ammonium acetate (0.8g) was added and further stirred at 55-60 0C for 20 hrs. The reaction mixture was cooled to 25-30 0C then after water was added and extract with ethyl acetate (50ml). Organic layer was separated and washed with 10 % sodium bicarbonate solution, dried and concentrated to dryness <; 500C to obtain Etoricoxib.Yield = 3.1 g, (12.82 %), HPLC purity = 15.36% (Etoricoxib), (unreacted 64.15 %-sulfone compound).

References: [1]Patent: WO2010/97802,2010,A2 .Location in patent: Page/Page column 15.

23
2-chloro-1,3-(bis-piperidinyl)trimethinium hexafluorophosphate [ No CAS ]
[ 221615-75-4 ]
[ 202409-33-4 ]

Yield	Reaction Conditions	Operation in experiment
75.9%		Example-5; Preparation of Etoricoxib; Potassium tert. butoxide (2.Ig) was dissolved in THF (20ml) and the solution was maintained at 5-25 0C for 10 minutes. Subsequently, a solution of l-(6-methylpyridin-3- yl)-2[4-(rnethylsulfonyl)phenyl] ethanone (5g) in THF was added and kept the mixture for lhr at 25-30 0C. 2-chloro l,3-(bis piperidyl) trimethinium hexafluoro phosphate salt of formula (HIc) (8g), obtained in Example 4 above, in THF, was added to the previously prepared solution of ketosulfone and the reaction mixture was heated at 30-55 0C for 2-24 hrs. The reaction mixture was dumped into a mixture of triflorbacetic acid (Ig), acetic acid (7.5g) and THF. The reaction mixture was further heated to 55-60 0C for 6-20 hrs, after adding ammonia solution (125 ml). Then cooled the reaction mixture to room temperature. The reaction mixture was dumped into water and extracted with ethyl acetate and washed with 10% aqueous sodium bicarbonate solution. The organic layer was separated and concentrated to dryness at less than 50 0C to give Etoricoxib 8.6 g. HPLC purity- 91.28 % (Etoricoxib). Crude mass was purified to obtain Etoricoxib (4.7g), yield = 75.9 %; HPLC purity = 96.31 %.

References: [1]Patent: WO2010/97802,2010,A2 .Location in patent: Page/Page column 14.

24
2-chloro-1,3-(bis-pyrrolidinyl)trimethinium hexafluorophosphate [ No CAS ]
[ 221615-75-4 ]
[ 202409-33-4 ]

Yield	Reaction Conditions	Operation in experiment
		ExampIe-9; Preparation of Etoricoxib; Potassium tert. butoxide (0.426g) was dissolved in THF (40ml) and the solution was maintained at 25-30 0C for 10 minutes and then cooled to 10-15 0C. Subsequently, solution of l-(6-methylpyridin-3-yl)-2[4-(methylsulfonyl)phenyl] ethanone (Ig) in THF was added and kept the mixture for lhr at 10-15 0C. Subsequently, 2-chloro l,3-(bis pyrolidinyl) trimethinium hexafluoro phosphate salt (1.3g), in THF (8ml) was added and maintained the reaction mixture for 2 hrs at 25-30 0C. The reaction mixture was dumped in to the mixture of trifloroaceticacid (0.2g), acetic acid (1.5g), and THF (10ml) and maintained for 1 hour at 25-30 0C. Further the reaction mixture was heated at 60-70 0C for 15 hrs after aq. ammonia solution (25ml) was added and the reaction mixture was cooled to 25-30 0C. After then ethyl acetate and water was added, organic layer was separated and washed with water and 10 % sodium bicarbonate solution. Organic layer was separated, dried and concentrated to dryness <; 50 0C to give crude Etoricoxib. Yield = 0.9 g (40.84 %), % HPLC purity = 55.82 % (Etoricoxib), (unreacted sulfone compound = 34.44 %).

References: [1]Patent: WO2010/97802,2010,A2 .Location in patent: Page/Page column 16.

25
[ 221615-75-4 ]
5-chloro-6'-methyl-3-[4-(methylsulfonyl)phenyl]-2,3'-bipyridine oxalate [ No CAS ]