[ CAS No. 39614-62-5 ] {[proInfo.proName]}

Name: 39614-62-5|3,4,5-Trimethoxybenzene-1-sulfonyl chloride|95%
Brand: Ambeed
SKU: A150365
Price: 120.0 USD
Availability: InStock
Rating: 92 (25 reviews)

,{[proInfo.pro_purity]}

Cat. No.: {[proInfo.prAm]}

HazMat Fee +

There will be a HazMat fee per item when shipping a dangerous goods. The HazMat fee will be charged to your UPS/DHL/FedEx collect account or added to the invoice unless the package is shipped via Ground service. Ship by air in Excepted Quantity (each bottle), which is up to 1g/1mL for class 6.1 packing group I or II, and up to 25g/25ml for all other HazMat items.

Type	HazMat fee for 500 gram (Estimated)
Excepted Quantity	USD 0.00
Limited Quantity	USD 15-60
Inaccessible (Haz class 6.1), Domestic	USD 80+
Inaccessible (Haz class 6.1), International	USD 150+
Accessible (Haz class 3, 4, 5 or 8), Domestic	USD 100+
Accessible (Haz class 3, 4, 5 or 8), International	USD 200+

DV 2D 3D

3d Animation Molecule Structure of 39614-62-5

Structure of 39614-62-5 * Storage: {[proInfo.prStorage]}

Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Search after Editing

* Storage: {[proInfo.prStorage]}

For Research Only 110K+ Compounds Competitive Price 1-2 Day Shipping

Quality Control of [ 39614-62-5 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 39614-62-5 ]

SDS Specification

Alternatived Products of [ 39614-62-5 ]

Product Details of [ 39614-62-5 ]

CAS No. :	39614-62-5	MDL No. :	MFCD05664176
Formula :	C₉H₁₁ClO₅S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	MQSMMBMVEDEDQR-UHFFFAOYSA-N
M.W :	266.70	Pubchem ID :	15196158
Synonyms :

Calculated chemistry of [ 39614-62-5 ]

Physicochemical Properties

Num. heavy atoms :	16
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.33
Num. rotatable bonds :	4
Num. H-bond acceptors :	5.0
Num. H-bond donors :	0.0
Molar Refractivity :	59.0
TPSA :	70.21 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.88 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.37
Log Po/w (XLOGP3) :	1.47
Log Po/w (WLOGP) :	2.72
Log Po/w (MLOGP) :	0.71
Log Po/w (SILICOS-IT) :	1.4
Consensus Log Po/w :	1.73

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.43
Solubility :	0.984 mg/ml ; 0.00369 mol/l
Class :	Soluble
Log S (Ali) :	-2.55
Solubility :	0.75 mg/ml ; 0.00281 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.32
Solubility :	0.126 mg/ml ; 0.000474 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	0.0
Synthetic accessibility :	2.51

Safety of [ 39614-62-5 ]

Signal Word:	Danger	Class:	8
Precautionary Statements:	P260-P280-P303+P361+P353-P301+P330+P331-P304+P340+P310-P305+P351+P338+P310	UN#:	3261
Hazard Statements:	H314	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 39614-62-5 ]

* 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 [ 39614-62-5 ]

[ 39614-62-5 ] Synthesis Path-Downstream 1~45

1
[ 504-72-3 ]
[ 39614-62-5 ]
[ 42771-34-6 ]

Reference： [1]Journal of Pharmaceutical Sciences,1973,vol. 62,p. 1392 - 1394

2
[ 7755-92-2 ]
[ 39614-62-5 ]
4-(3,4,5-Trimethoxy-benzenesulfonyl)-piperazine-1-carbaldehyde [ No CAS ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1994,vol. 42,p. 541 - 550

3
[ 39614-62-5 ]
[ 81453-48-7 ]

Reference： [1]Chimica Therapeutica,1972,vol. 7,p. 466 - 469

4
[ 39614-62-5 ]
[ 111-92-2 ]
[ 39614-65-8 ]

Reference： [1]Chimica Therapeutica,1972,vol. 7,p. 466 - 469

5
[ 39614-62-5 ]
[ 109-89-7 ]
[ 39614-64-7 ]

Reference： [1]Chimica Therapeutica,1972,vol. 7,p. 466 - 469

6
[ 24313-88-0 ]
[ 39614-62-5 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; CuCl2; sulfur dioxide; sodium nitrite; In water; acetic acid;	EXAMPLE 21A 3,4,5-trimethoxybenzenesulfonyl chloride The procedure in J. Het. Chem. 23, 1253 (1986) was followed. A solution of 3,4,5-trimethoxyaniline (5.0 g) in acetic acid (26 mL) and 12M HCl (47 mL) at -10-5 C. was treated slowly with a solution of NaNO2 (2 g) in water (7 mL), stirred at -5 C. for another 30 minutes, added in portions to a cold (-5 C.) solution of CuCl2 and SO2 in acetic acid (35 mL) and water (6 mL), stirred at -5-0 C. for 3 hours, warmed to room temperature overnight, poured over ice, filtered, and dried to provide the desired product.
		3,4,5-trimethoxybenzenesulfonyl chloride The procedure in J. Het. Chem. 23,1253 (1986) was followed.. A solution of 3,4,5-trimethoxyaniline (5.0 g) in acetic acid (26 ML) and 12M HCl (47 ML) at -10-5 C was treated slowly with a solution of NaNO2 (2 g) in water (7 ML), stirred at -5 C for another 30 minutes, added in portions to a cold (-5 C) solution of CuCl2 and SO2 in acetic acid (35 ML) and water (6 ML), stirred at -5-0 C for 3 hours, warmed to room temperature overnight, poured over ice, filtered, and dried to provide the desired product.

Reference： [1]European Journal of Medicinal Chemistry,2001,vol. 36,p. 809 - 828
[2]Chemical Communications,2019,vol. 55,p. 11864 - 11867
[3]Chimica Therapeutica,1972,vol. 7,p. 466 - 469
[4]Journal of Pharmaceutical Sciences,1973,vol. 62,p. 1392 - 1394
[5]Patent: US6521658,2003,B1
[6]Patent: EP1181269,2004,B1 .Location in patent: Page 15
[7]ChemMedChem,2011,vol. 6,p. 1119 - 1129

7
[ 39614-62-5 ]
[ 4321-58-8 ]
[ 42771-37-9 ]

Reference： [1]Journal of Pharmaceutical Sciences,1973,vol. 62,p. 1392 - 1394

8
[ 39614-62-5 ]
[ 42771-33-5 ]

Reference： [1]Journal of Pharmaceutical Sciences,1973,vol. 62,p. 1392 - 1394

9
[ 39614-62-5 ]
[ 42771-39-1 ]
[ 42771-36-8 ]

Reference： [1]Journal of Pharmaceutical Sciences,1973,vol. 62,p. 1392 - 1394

10
[ 1953-54-4 ]
[ 39614-62-5 ]
1H-indol-5-ol,(3,4,5-trimethoxybenzenesulfonate) ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	dmap; In pyridine; dichloromethane; for 168h;	Example 15 1H-indol-5-ol,(3,4,5-trimethoxybenzenesulfonate) ester A solution of 5-hydroxyindole (CAS number 13523-92-7,253 mg, 1.9 mmol) in dichloromethane (15 ML) and pyridine (0. 5 ML) was treated sequentially with Example 12A (507 mg, 1.9 mmol) and a catalytic amount of DMAP, stirred for 1 week, and washed with saturated CuSO4.. The organic layer was dried (MgSO4), filtered, and concentrated.. Chromatography ofthe concentrate on silica gel with 30% ethyl acetate/hexane provided 520 mg of the desired compound as a white crystalline solid. MS(ESI/NH3) m/z 364(M+H)+;1H NMR (300 MHz, CDCl3) delta 8.24 (br s, 1H), 7.29-7.25 (m, 3H), 7.02 (s, 2H), 6.82 (dd, J=2.2, 8.8, 1H), 6.51 (m, 1H), 3.92 (s, 3H), 3.78 (s, 6H).

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2001,vol. 11,p. 871 - 874
[2]Patent: EP1181269,2004,B1 .Location in patent: Page 16

11
[ 13523-92-7 ]
[ 39614-62-5 ]
1-methyl-1H-indol-5-yl 3,4,5-trimethoxybenzenesulfonate [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2001,vol. 11,p. 871 - 874

12
[ 100-02-7 ]
[ 39614-62-5 ]
[ 312299-84-6 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2001,vol. 11,p. 871 - 874

13
[ 106-44-5 ]
[ 39614-62-5 ]
4-methylphenyl 3,4,5-trimethoxybenzenesulfonate [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2001,vol. 11,p. 871 - 874

14
[ 40357-87-7 ]
[ 39614-62-5 ]
1-methyl-2-oxo-1,2-dihydro-4-pyridinyl 3,4,5-trimethoxybenzenesulfonate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In 1,4-dioxane; ethyl acetate; N,N-dimethyl-formamide;	EXAMPLE 63 1-methyl-2-oxo-1,2-dihydro-4-pyridinyl 3,4,5-trimethoxybenzenesulfonate A solution of 4-hydroxy-1-methyl-1H-pyridin-2-one ([40357-87-7], 44.9 mg, 0.358 mmol) in dioxane (2 mL) and DMF (1 mL) was treated with triethylamine (0.15 mL) and 3,4,5-trimethoxybenzenesulfonylchloride (97.1 mg, 0.358 mmol), stirred for 48 hours at room temperature, diluted with ethyl acetate, washed with 1.1M NaHSO4, dried (MgSO4), filtered and concentrated. Chromatography of the concentrate on silica gel with 40% ethyl acetate/hexane provided 47 mg of the desired compound. MS (ESI) m/z 356 (M+H)+; 1H NMR (300 MHz, CDCl3) 7.29 (d, J=7.5, 1H), 7.11 (s, 2H), 6.21 (d, J=2.4, 1H), 6.13 (dd, J=2.7, 7.5, 1H), 3.94 (s, 3H), 3.92 (s, 6H), 3.51 (s, 3H).

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2001,vol. 11,p. 871 - 874
[2]Patent: US6521658,2003,B1

15
[ 39614-62-5 ]
[ 150-76-5 ]
4-methoxyphenyl 3,4,5-trimethoxybenzenesulfonate [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2001,vol. 11,p. 871 - 874

16
[ 39614-62-5 ]
[ 187228-99-5 ]
[ 426819-97-8 ]

Reference： [1]European Journal of Medicinal Chemistry,2001,vol. 36,p. 809 - 828

17
[ 39614-62-5 ]
2-octyl-1-(3,4,5-trimethoxy-benzenesulfonyl)-piperazine; hydrochloride [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,2001,vol. 36,p. 809 - 828

18
[ 39614-62-5 ]
[ 312299-85-7 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2001,vol. 11,p. 871 - 874

19
[ 39614-62-5 ]
[ 133263-81-7 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1994,vol. 42,p. 541 - 550

20
[ 39614-62-5 ]
(2,3-Dimethoxy-8,9-dihydro-7H-benzocyclohepten-6-yl)-[4-(3,4,5-trimethoxy-benzenesulfonyl)-piperazin-1-yl]-methanone [ No CAS ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1994,vol. 42,p. 541 - 550

21
[ 6307-90-0 ]
[ 39614-62-5 ]

Reference： [1]Journal of Pharmaceutical Sciences,1973,vol. 62,p. 1392 - 1394

22
[ 118-41-2 ]
[ 39614-62-5 ]

Reference： [1]Journal of Pharmaceutical Sciences,1973,vol. 62,p. 1392 - 1394

23
[ 42543-45-3 ]
[ 39614-62-5 ]

Reference： [1]Chimica Therapeutica,1972,vol. 7,p. 466 - 469

24
[ 3086-62-2 ]
[ 39614-62-5 ]

Reference： [1]Chimica Therapeutica,1972,vol. 7,p. 466 - 469

25
[ 4521-61-3 ]
[ 39614-62-5 ]

Reference： [1]Chimica Therapeutica,1972,vol. 7,p. 466 - 469
[2]Chimica Therapeutica,1972,vol. 7,p. 466 - 469

26
[ 39614-62-5 ]
[ 104-94-9 ]
3,4,5-trimethoxy-N-(4-methoxyphenyl)benzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In tetrahydrofuran; pyridine; water;	EXAMPLE 21B 3,4,5-trimethoxy-N-(4-methoxyphenyl)benenesulfonamide A solution of 4-methoxyaniline (139 mg, 1.1 mmol) in pyridine (2 mL) was treated with Example 21A (300 mg, 1.1 mmol) in THF (2 mL), stirred at room temperature for 18 hours, concentrated, redissolved in THF (1 mL), treated with water with stirring, and filtered to provide 300 mg of the desired product. MS (DCI/NH3) m/z 353 (M+H)+and 371 (M+NH4)+; 1H NMR (300 MHz, CDCl3) delta6.99 (d, J=9 Hz, 1H), 6.80 (d, J=9 Hz, 1H), 6.85 (s, 2H), 3.87 (s, 3H), 3.77 (s, 3H), 3.76 (s, 6H).
	In tetrahydrofuran; pyridine; at 20℃; for 18h;	Example 12B 3,4,5-trimethoxy-N-(4-methoxyphenyl)benenesulfonamide A solution of 4-methoxyaniline (139 mg, 1.1 mmol) in pyridine (2 ML) was treated with Example 12A (300 mg, 1.1 mmol) in THF (2 ML), stirred at room temperature for 18 hours, concentrated, redissolved in THF (1 ML), treated with water with stirring, and filtered to provide 300 mg of the desired product. MS (DCI/NH3) m/z 353 (M+H)+ and 371 (M+NH4)+;1H NMR (300 MHz, CDCl3) delta 6.99 (d, J=9 Hz, 1H), 6.80 (d, J=9 Hz, 1H), 6.85 (s, 2H), 3.87 (s, 3H), 3.77 (s, 3H), 3.76 (s, 6H).

Reference： [1]Patent: US6521658,2003,B1
[2]Patent: EP1181269,2004,B1 .Location in patent: Page 15

27
[ 80-73-9 ]
[ 39614-62-5 ]
[ 75-78-5 ]
[ 7440-66-6 ]
[ 16807-30-0 ]

Yield	Reaction Conditions	Operation in experiment
	In methanol; 1,2-dichloro-ethane;	EXAMPLE 85A 3,4,5-trimethoxybenzenethiol A room temperature suspension of zinc powder (430 mg, 6.56 mmol) and dichlorodimethylsilane (0.80 mL, 6.59 mmol) in 1,2-dichloroethane (15 mL) was treated with a solution of <strong>[39614-62-5]3,4,5-trimethoxybenzenesulfonyl chloride</strong> (500 mg, 1.87 mmol) and 1,3-dimethyl-2-imidazolidinone (647 mg, 5.67 mmol) in 1,2-dichloroethane (15 mL). The reaction was heated to 75 C. for 1 hour, cooled to room temperature, filtered, and concentrated. The concentrate was dissolved in methanol, concentrated, dissolved in methanol, and concentrated. The concentrate was purified by flash column chromatography on silica gel with dichloromethane to provide the desired product.

Reference： [1]Patent: US6521658,2003,B1

28
[ 39614-62-5 ]
[ 85696-95-3 ]
[ 312299-54-0 ]

Yield	Reaction Conditions	Operation in experiment
	In tetrahydrofuran; pyridine; water;	EXAMPLE 29C 3,4,5-trimethoxy-N-(1-methyl-1H-indol-4-yl)benzenesulfonamide Example 29B (82 mg, 0.56 mmol) was dissolved in pyridine (1 mL), treated portionwise with Example 21A, (150 mg, 0.56 mmol) in THF (1 mL), stirred for 18 hours, concentrated, treated with a small amount of THF to dissolve the concentrate, and treated with water with vigorous stirring. The precipitate was filtered and dried in a vacuum oven to provide 180 mg of the desired product. MS (DCI/NH3) m/z 377 (M+H)+and 394 (M+NH4)+; 1H NMR (300 MHz, CDCl3) delta9.93 (s, 1H), 7.20 (d, J=3 Hz, 1H), 7.18 (d, J=6 Hz, 1H), 7.05 (d, J=7.5 Hz, 1H), 6.99 (s, 2H), 6.95 (dd, J=0.6, 7.5 Hz, 1H), 3.71 (s, 3H), 3.68 (s, 6H), 3.64 (s, 3H).

Reference： [1]Patent: US6521658,2003,B1

29
[ 7755-92-2 ]
[ 39614-62-5 ]
[ 133263-81-7 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; sodium chloride; triethylamine; In tetrahydrofuran; methanol; dichloromethane;	PREPARATION 109 N-(3,4,5-Trimethoxybenzenesulfonyl)piperazine 75 ml of a methylene chloride solution containing 7.40 g of <strong>[39614-62-5]3,4,5-trimethoxybenzenesulfonyl chloride</strong> were dropped into 150 ml of a methylene chloride solution containing 3.80 g of N-formylpiperazine and 7.73 ml of triethylamine in an ice bath. The mixture was then stirred for 30 minutes at 0 to 5 C., after which it was poured into water and extracted twice with methylene chloride. The combined methylene chloride extracts were washed with 10% w/v aqueous hydrochloric acid and with a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate and condensed by evaporation under reduced pressure. The residue (9.86 g) was dissolved in a mixture of 150 ml of tetrahydrofuran, 75 ml of methanol and 50 ml of a 10% w/v aqueous solution of sodium hydroxide, and then stirred for 14 hours at room temperature. At the end of this time, the reaction solution was poured into water and extracted 4 times with methylene chloride. The combined methylene chloride extracts were washed with water, dried over anhydrous sodium sulfate and condensed by evaporation under reduced pressure. The residue was crystallized from a mixture of hexane and ethyl acetate, to give 7.02 g of the title compound as crystals, melting at 131 to 133 C. Nuclear Magnetic Resonance Spectrum (CDCl3, 270 MHz) delta ppm: 2.90-3.10 (8H, multiplet); 3.91 (9H, singlet); 6.96 (2H, singlet). Mass spectrum (m/z): 316 (M+), 232, 85. Elemental analysis: Calculated for C13 H20 N2 O5 S: C, 49.35%; H, 6.37%; N, 8.85%; S, 10.13%. Found: C, 49.62%; H, 6.30%; N, 8.55%; S, 10.11%.

Reference： [1]Patent: US5192766,1993,A

30
[ 1687-53-2 ]
[ 39614-62-5 ]
1-[(3-Hydroxy-4-methoxyphenyl)aminosulfonyl]-3,4,5-trimethoxybenzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
430 mg (62%)	In methanol;	EXAMPLE 1 1[(3-Hydroxy-4-methoxyphenyl)aminosulfonyl]-3,4,5-trimethoxybenzene To a solution of <strong>[39614-62-5]3,4,5-trimethoxybenzenesulfonyl chloride</strong> (500 mg, 1.88 mmol) in methanol (10 mL) was added 3-hydroxy4-methoxyaniline (523 mg, 3.76 mmol) at ambient temperature. After stirring for 1 h, the reaction mixture was concentrated and the crude residue was purified by chromatography over silica to afford 430 mg (62%) of product as fme white needles, m.p. 145-146 C. 1H-NMR (CDCl3): delta9.74 (1H, s), 9.15 (1H, s), 6.98 (2H, s), 6.78 (1H, d, J=8.8 Hz), 6.63 (1H, d, J=2.6 Hz), 6.50 (1H, dd, J=8.8, 2.6 Hz), 3.76 (6H, s), 3.70 (3H, s), 3.68 (3H, s). Anal. Calcd. for C16H19N1O7S: C, 52.03; H, 5.18; N, 3.79; S, 8.68. Found: C, 51.87; H, 5.28; N, 3.76; S, 8.77.
430 mg (62%)	In methanol;	Example K 1-[(3-Hydroxy-4-methoxyphenyl)aminosulfonyl]-3,4,5-trimethoxybenzene To a solution of <strong>[39614-62-5]3,4,5-trimethoxybenzenesulfonyl chloride</strong> (500 mg, 1.88 nmol) in methanol (10 mL) was added 3-hydroxy-4-methoxyaniline (523 mg, 3.76 mmol) at ambient temperature. After stirring for 1 h, the reaction mixture was concentrated and the crude residue was purified by chromatography over silica to afford 430 mg (62%) of product as fine white needles, m.p. 145-146 C. 1H-NMR (CDCl3): delta 9.74 (1H, s), 9.15 (1H, s), 6.98 (2H, s), 6.78 (1H, d, J=8.8 Hz), 6.63 (1H, d, J=2.6 Hz), 6.50 (1H, dd, J=8.8, 2.6 Hz), 3.76 (6H, s), 3.70 (3H, s), 3.68 (3H, s). Anal. Calcd. for C,16H19N1O7S: C, 52.03; H, 5.18; N, 3.79; S, 8.68. Found: C, 51.87; H, 5.28; N, 3.76; S, 8.77.

Reference： [1]Patent: US6191170,2001,B1
[2]Patent: US6211167,2001,B1

31
aqueous sodium nitrite [ No CAS ]
[ 24313-88-0 ]
[ 39614-62-5 ]

Yield	Reaction Conditions	Operation in experiment
	With sulfur dioxide; In hydrogenchloride; acetic acid; aniline;	Example J 3,4,5-Trimethoxybenzenesulfonyl Chloride 3,4,5-Trimethoxybenzenesulfonyl chloride was synthesised from 3,4,5-trimethoxyaniline according to the procedure described in G. Pifferi and R. Monguzzi, Journal of Pharmaceutical Sciences, 1973, 62, 1393. In this procedure the aniline was dissolved in concentrated hydrochloric acid and to the resulting mixture was added a solution of aqueous sodium nitrite at 0 C., the resulting mixture containing the desired diazonium salt was added at 5 C. to a saturated solution of sulfur dioxide in glacial acetic acid containing substoichiometric amount of cuprous chloride. The mixture was stirred at ambient temperature for 3 h, poured into cold water, and the product extracted with dichloromethane. The solvent was evaporated and the solid residue was recrystallized from hexanes.

Reference： [1]Patent: US6211167,2001,B1

32
[ 1314324-71-4 ]
[ 39614-62-5 ]
[ 1314324-97-4 ]

Reference： [1]Journal of Asian Natural Products Research,2011,vol. 13,p. 330 - 340

33
[ 39614-62-5 ]
[ 5192-04-1 ]
[ 110-13-4 ]
[ 1334246-06-8 ]

Yield	Reaction Conditions	Operation in experiment
		Embodiment 19: Preparation of Compound 6i (N-(5,8-Dimethyl-9H-carbazol-1-yl)-3,4,5-trimethoxybenzenesulfonamide)); A mixture of 4 (0.5 g, 3.08 mmol) and 10% Pd/C (0.2 g) in methanol (30 mL) was stirred under hydrogen for 1 hour. Pd/C was removed by filtration and filtrate was evaporated in vacuo to yield oily product. To the product, ethyl acetate (30 mL) and 3,4,5-trimethoxybenzenesulfonyl chloride (0.9 g, 3.38 mmol) were added and stirred at 50 C for 1 hour. The reaction was roughly purified by passing through silica gel packed funnel and wash with ethyl acetate. The filtrate was evaporated in vacuo and the crude product was reacted with acetonylacetone (0.5 mL, 4.38 mmol) in the presence of p-toluenesulfonic acid (0.7 g, 4.06 mmol) in EtOH (20 mL) at reflux for 3 hours. Finally, the mixture was purified with column chromatography and recrystalization in ethanol to afford white solids, compound 6i (0.66 g, 48.37 %; Hex/EA = 4/1, Rf= 0.2). mp = 205-207 C; ESI (M-H+) 439.1; 1H NMR (200 Hz, DMSO-d6) delta 2.07 (s, 3H, CH3), 2.68 (s, 3H, CH3), 3.43 (s, 3H, OCH3), 3.62 (s, 6H, OCH3), 6.82 (d, J= 7.2 Hz, 1H, ArH), 6.95 (s, 2H, ArH), 7.00-7.15 (m, 2H, ArH), 7.37 (d, J= 7.6 Hz, 1H, ArH), 7.87 (d, J= 7.6 Hz, 1H, ArH), 7.72 (s, 1H, NH), 10.51 (s, 1H, NH); 13C NMR (50 Hz, DMSO-d6) delta16.37,20.07,55.99,59.87,104.24,117.27, 118.38, 119.12, 119.31, 120.32, 120.56, 121.15, 124.77, 126.15, 129.82, 132.85, 133.96, 138.45, 140.67, 152.50. Anal. (C23H24N2O5S): Calcd, C, 62.71; H, 5.49; N, 6.36; S, 7.28; Found, C, 62.75; H, 5.69; N, 6.59; S, 7.10.

Reference： [1]Patent: EP2366687,2011,A2 .Location in patent: Page/Page column 24-25

34
[ 607-67-0 ]
[ 39614-62-5 ]
[ 1313356-71-6 ]