41608-73-5|2-Methoxy-4-(methylsulfonyl)aniline| Ambeed

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Quality Control of [ 41608-73-5 ] Purity: 98% SDS Specification

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Product Details of [ 41608-73-5 ]

CAS No. :	41608-73-5
Formula :	C₈H₁₁NO₃S
M.W :	201.24
SMILES Code :	NC1=CC=C(S(=O)(C)=O)C=C1OC
MDL No. :	MFCD18861008
InChI Key :	FBZRMLLLOMNOLJ-UHFFFAOYSA-N
Pubchem ID :	22316785

Safety of [ 41608-73-5 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302
Precautionary Statements:	P280-P305+P351+P338

Computational Chemistry of [ 41608-73-5 ] Show Less

Physicochemical Properties

Num. heavy atoms	13
Num. arom. heavy atoms	6
Fraction Csp3	0.25
Num. rotatable bonds	2
Num. H-bond acceptors	3.0
Num. H-bond donors	1.0
Molar Refractivity	50.43
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	77.77 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.27
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	0.47
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.77
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.	0.65
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	0.42
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	0.91

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-1.59
Solubility	5.13 mg/ml ; 0.0255 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.	-1.67
Solubility	4.28 mg/ml ; 0.0213 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	-2.48
Solubility	0.66 mg/ml ; 0.00328 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	No
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	No
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.	-7.19 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	1.0 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)	2.19

Application In Synthesis of [ 41608-73-5 ]

* 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 [ 41608-73-5 ]

[ 41608-73-5 ] Synthesis Path-Downstream 1~21

Yield	Reaction Conditions	Operation in experiment
96%	With iron; ammonium chloride; In ethanol; water; at 75.0℃; for 3.0h;	General procedure: Iron powder (0.83 g, 14.87 mmol) was added to a solution of intermediate 31(0.96 g, 2.97 mmol), NH4C1 (0.64 g; 11.90 mmol) in EtOH (8.34 mL) and distilled water (4.19 mL). The reaction mixture was stirred at 75 CC for 3 h. The reaction mixture wasfiltered over a pad of celite® and washed with DCM. A saturated solution of NaHCO3 was added and the mixture was extracted with DCM. The organic layer was dried over MgSO4, filtered and evaporated to dryness to give 701 mg of intermediate 32 (81percent yield, brown oil).

2
[ 41608-73-5 ]
[ 87-13-8 ]
C₁₆H₂₁NO₇S [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 1380 - 1385.

3
2-methoxy-4-(methylsulfonyl)-1-nitrobenzene [ No CAS ]
[ 41608-73-5 ]

Yield	Reaction Conditions	Operation in experiment
92%	With palladium 10% on activated carbon; hydrogen; In ethanol; under 760.051 Torr; for 18.0h;	Step 3: 2-Methoxy-4-(methylsulfonyl)aniline A suspension of 2-methoxy-4-(methylsulfonyl)-l -nitrobenzene (0.175 g, 0.76 mmol) and palladium on carbon (10 wtpercent, 0.10 g) in ethanol (10 mL) was stirred under hydrogen at one atmosphere pressure for 18 hours. The reaction was filtered through celite and concentrated to give 2-methoxy-4-(methylsulfonyl)aniline (0.15 g, 92percent).
68%	With ammonium chloride; zinc; In ethanol; water; at 80.0℃; for 2.0h;	Compound 34-f (1.7 g, 7.36 mmol) was dissolved in a mixed solution of ethanol (20 mL) and water (20 mL).Ammonium chloride (2.0 g, 36.79 mmol) and zinc powder (2.4 g, 36.79 mmol) was added thereto. The reaction mixturewas stirred at 80°C for 2 hours. The reaction solution was cooled to room temperature, diluted with water (200 mL) andextracted with ethyl acetate (200 mL). The organic phase was washed successively with water (50 mL 3 3) and brine(50 mL), dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure todelivera brown oil 34-e (1 g, yield: 68percent). This product was used without further purification. LC-MS (ESI): m/z = 202 [M+H]+.
	With ammonium chloride; zinc; In ethanol; water; at 80.0℃; for 2.0h;	Compound 4-d (1.7 g, 7.36 mmol) was dissolved in ethanol (20 mL) and water (20 mL) and ammonium chloride (2 g, 36.79 mmol) and zinc dust (2.4 g, 36.79 mmol) were added. The mixture was heated to 80° C. to react for 2 hours. After cooling to room temperature, the mixture was concentrated under reduced pressure. The residue was partitioned between ethyl acetate (200 mL) and water (200 mL). The organic phase was separated, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure to give 4-c as a brown oil (1 g, yield 68percent), which was used without further purification. LC-MS (ESI): m/z=202[M+H]+.

References: [1]Patent: WO2013/79493,2013,A1 .Location in patent: Page/Page column 45.
[2]Patent: EP3287463,2018,A1 .Location in patent: Paragraph 0263; 0266.
[3]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 1380 - 1385.
[4]Patent: US2018/208604,2018,A1 .Location in patent: Paragraph 0170-0171.

4
[ 515824-43-8 ]
[ 41608-73-5 ]
[ 1441720-56-4 ]

Yield	Reaction Conditions	Operation in experiment
20%	With trifluoroacetic acid; In butan-1-ol; at 100.0℃; for 1.5h;Sealed tube;	Example 1 : N2-(2-Methoxy-4-(methylsulfonyl)phenyl)-N4-methyl-5- (trifLuoromethyl)pyrimidine-2,4-diamine To a mixture of <strong>[41608-73-5]2-methoxy-4-(methylsulfonyl)aniline</strong> (0.095 g, 0.47 mmol) and 2- chloro-N-methyl-5-(trifluoromethyl)pyrimidin-4-amine (0.10 g, 0.47 mmol) in 1-butanol (1.5 mL) was added TFA (0.036 mL, 0.047 mmol). The reaction was stirred in a sealed tube at 100 °C for 1.5 h. The reaction was concentrated and the product was isolated by reverse-phase HPLC to give N2-(2-methoxy-4-(methylsulfonyl)phenyl)-N4-methyl-5- (trifluoromethyl)pyrimidine-2,4-diamine (0.18 g, 20percent). 1H NMR (400 MHz, DMSO) ? 8.58 (d, J = 12.9, 1H), 8.24 (d, J = 5.0, 2H), 7.53 (d, J = 10.1, 1H), 7.48 (s, 1H), 7.38 - 7.29 (m, 1H), 3.99 (s, 3H), 3.20 (s, 3H), 2.94 (d, J = 4.3, 3H); LRRK2 Ki = 0.002.

References: [1]Patent: WO2013/79493,2013,A1 .Location in patent: Page/Page column 46-47.

5
[ 860734-15-2 ]
[ 41608-73-5 ]

References: [1]Patent: WO2013/79493,2013,A1 .
[2]Patent: EP3287463,2018,A1 .

6
[ 448-19-1 ]
[ 41608-73-5 ]

References: [1]Patent: WO2013/79493,2013,A1 .
[2]Patent: EP3287463,2018,A1 .
[3]Patent: US2018/208604,2018,A1 .

7
[ 41608-73-5 ]
8-(4-methylsulfonyl-2-methoxyphenyl)-N-[4-(piperidin-4-yl)-2,3-dihydro-1-benzofuran-7-yl]oxazolin-2-amine [ No CAS ]

References: [1]Patent: EP3287463,2018,A1 .

8
[ 41608-73-5 ]
8-(4-methylsulfonyl-2-methoxyphenyl)-N-[2-methyl-4-(piperidin-4-yl)-2,3-dihydro-1-benzofuran-7-yl]quinazolin-2-amine [ No CAS ]

References: [1]Patent: EP3287463,2018,A1 .

9
[ 41608-73-5 ]
7-[8-(4-methylsulfonyl-2-methoxyphenyl)quinazolin-2-yl]amino}2,3-dihydro-1-benzofuran-4-carboxamide [ No CAS ]

References: [1]Patent: EP3287463,2018,A1 .

10
[ 41608-73-5 ]
[ 90531-98-9 ]

Yield	Reaction Conditions	Operation in experiment
41%	With tert.-butylnitrite; copper(ll) bromide; In acetonitrile; at 80.0℃; for 1.0h;	Compound 34-e (1.0 g, 4.98 mmol) was dissolved in acetonitrile (10 mL), copper(II) bromide (1.9 g, 7.50 mmol)was added and tert-butyl nitrite (0.73 mL) was added slowly thereto. The reaction mixture was stirred at 80°C for 1 hour.The reaction mixture was cooled to room temperature, diluted with water (50 mL) and extracted with ethyl acetate (100mL). The organic phase was washed successively with water (50 mL 3 3) and brine (50 mL), dried over anhydroussodium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gelcolumn chromatography (petroleum ether: ethyl acetate = 1:1) to delivera pale yellow solid 34-d (540 mg, yield: 41percent).LC-MS (ESI): m/z = 202 [M+H]+.
540 mg	With tert.-butylnitrite; copper(I) bromide; In acetonitrile; at 80.0℃; for 1.0h;	Compound 4-c (1 g, 4.98 mmol) was dissolved in acetonitrile (10 mL) and copper bromide (1.9 g, 7.50 mmol) was added, followed by slowly adding tert-butyl nitrite (0.73 mL). The mixture was heated to 80° C. and reacted for 1 hour, cooled to room temperature and then concentrated under reduced pressure. The residue was diluted with ethyl acetate (100 mL) and water (50 mL) and filtered through celite. The combined organic phase was dried over anhydrous sodium sulfate, filtered and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (petroleum ether: ethyl acetate=1:1) to give 4-b as a pale yellow solid (540 mg, yield 41percent). LC-MS (ESI): m/z=265[M+H]+.

References: [1]Patent: EP3287463,2018,A1 .Location in patent: Paragraph 0263; 0267.
[2]Patent: US2018/208604,2018,A1 .Location in patent: Paragraph 0172-0173.

11
[ 41608-73-5 ]
[ 1614246-31-9 ]

References: [1]Patent: EP3287463,2018,A1 .
[2]Patent: US2018/208604,2018,A1 .

12
[ 41608-73-5 ]
C₁₆H₁₃ClN₂O₃S [ No CAS ]

References: [1]Patent: EP3287463,2018,A1 .
[2]Patent: US2018/208604,2018,A1 .

13
[ 41608-73-5 ]
C₃₄H₃₈N₄O₆S [ No CAS ]

References: [1]Patent: EP3287463,2018,A1 .

14
[ 41608-73-5 ]
C₃₅H₄₀N₄O₆S [ No CAS ]

References: [1]Patent: EP3287463,2018,A1 .

15
[ 41608-73-5 ]
2-(4-[7-(4-methylsulfonyl-2-methoxyphenyl)-6-methylthieno[3,2-d]pyrimidinyl-2-yl]amino}-1H-pyrazol-1-yl)-1-ethanol [ No CAS ]