[ CAS No. 41608-73-5 ] {[proInfo.proName]}

Name: 41608-73-5|2-Methoxy-4-(methylsulfonyl)aniline|98%
Brand: Ambeed
SKU: A110846
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Quality Control of [ 41608-73-5 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 41608-73-5 ]

Product Details of [ 41608-73-5 ]

CAS No. :	41608-73-5	MDL No. :	MFCD18861008
Formula :	C₈H₁₁NO₃S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	FBZRMLLLOMNOLJ-UHFFFAOYSA-N
M.W :	201.24	Pubchem ID :	22316785
Synonyms :

Calculated chemistry of [ 41608-73-5 ]

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 :	77.77 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-7.19 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.27
Log Po/w (XLOGP3) :	0.47
Log Po/w (WLOGP) :	1.77
Log Po/w (MLOGP) :	0.65
Log Po/w (SILICOS-IT) :	0.42
Consensus Log Po/w :	0.91

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	0.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-1.59
Solubility :	5.13 mg/ml ; 0.0255 mol/l
Class :	Very soluble
Log S (Ali) :	-1.67
Solubility :	4.28 mg/ml ; 0.0213 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.48
Solubility :	0.66 mg/ml ; 0.00328 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.19

Safety of [ 41608-73-5 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302	Packing Group:	N/A
GHS Pictogram:

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.

Upstream synthesis route of [ 41608-73-5 ]
Downstream synthetic route of [ 41608-73-5 ]

[ 41608-73-5 ] Synthesis Path-Upstream 1~2

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

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

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

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

[ 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 ]

Reference： [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]+.

Reference： [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.

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

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

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

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

Reference： [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 ]

Reference： [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 ]

Reference： [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 ]

Reference： [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]+.

Reference： [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 ]

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

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

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

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

Reference： [1]Patent: EP3287463,2018,A1

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

Reference： [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 ]