313346-23-5|5-(Chlorosulfonyl)-2,4-dimethylbenzoic acid| Ambeed

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Quality Control of [ 313346-23-5 ] Purity: 95% SDS Specification

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Product Details of [ 313346-23-5 ]

CAS No. :	313346-23-5
Formula :	C₉H₉ClO₄S
M.W :	248.68
SMILES Code :	O=C(O)C1=CC(S(=O)(Cl)=O)=C(C)C=C1C
MDL No. :	MFCD09049987
InChI Key :	FFRJDYMIRFLOCU-UHFFFAOYSA-N
Pubchem ID :	16777525

Safety of [ 313346-23-5 ]

GHS Pictogram:
Signal Word:	Danger
Hazard Statements:	H318
Precautionary Statements:	P280-P305+P351+P338
Class:	8
UN#:	3261
Packing Group:	Ⅲ

Application In Synthesis of [ 313346-23-5 ]

* 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 [ 313346-23-5 ]

[ 313346-23-5 ] Synthesis Path-Downstream 1~26

1
[ 313346-23-5 ]
2,4-dimethyl-5-sulfinobenzoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
99%	With sodium hydroxide; sodium sulfite; In water; at 20℃; for 18.0h;pH Ca. 9;	5-(Chlorosulfonyl)-2,4-dimethylbenzoic acid (248 mg) was added in portions to a stirred suspension of sodium sulphite (277 mg) in water (1 ml). 2M. aq. Sodium hydroxide (1 ml) was then added dropwise till the reaction mixture was pH 9. The reaction mixture was stirred for 18 h at rt to give a very pale brown solution. The solution was acidified to pH 1 by addition of 4M. aq. HC1 and after 10 minutes the suspension was cooled in ice and the solid collected by filtration to yield the title compound as a white solid. (232 mg, 99%)LCMS Method 2 - Tr = 0.73 mm (ESj (M+Hj 215

References: [1]Patent: WO2018/89433,2018,A1 .Location in patent: Paragraph 00369.
[2]Journal of Medicinal Chemistry,1997,vol. 40,p. 2017 - 2034.

2
[ 611-01-8 ]
[ 313346-23-5 ]

Yield	Reaction Conditions	Operation in experiment
90%	With chlorosulfonic acid; at 20 - 75℃;	2,4-Dimethylbenzoic acid (1.50 g 1 mmol) was added in portions with stirring to chlorosulfonic acid (5 ml) at 20 C. The reaction was stirred at 70-75 C overnight. The reaction was added dropwise with stirring to 2OOg ice / water. The beige precipitate was collected and washed well with water with filtration. The solid was taken up in ethyl acetate, dried over Na2SO4, filtered and concentrated in vacuo to yield the title compound as a pale grey solid (2.36g, 90%).1H NIVIR (500 MHz, Chloroform-d) 8.76 (s, 1H), 7.38 (s, 1H), 2.83 (s, 3H), 2.76 (s, 3H).

References: [1]Patent: WO2018/89433,2018,A1 .Location in patent: Paragraph 00368; 00623.
[2]Journal of Medicinal Chemistry,1997,vol. 40,p. 2017 - 2034.
[3]Angewandte Chemie - International Edition,2017,vol. 56,p. 248 - 253.
Angew. Chem.,2017,vol. 129,p. 254 - 259.

3
[ 313346-23-5 ]
[ 176641-71-7 ]

References: [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 2017 - 2034.

4
[ 313346-23-5 ]
N-diaminomethylene-2,4-dimethyl-5-methylsulfonylbenzamide [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 2017 - 2034.

5
C₂₉H₃₇N₃O [ No CAS ]
[ 313346-23-5 ]
C₃₈H₄₅N₃O₅S [ No CAS ]

References: [1]Angewandte Chemie - International Edition,2017,vol. 56,p. 248 - 253.
Angew. Chem.,2017,vol. 129,p. 254 - 259.

6
[ 313346-23-5 ]
C₂₉H₃₉N₅O₈S [ No CAS ]

References: [1]Angewandte Chemie - International Edition,2017,vol. 56,p. 248 - 253.
Angew. Chem.,2017,vol. 129,p. 254 - 259.

7
[ 313346-23-5 ]
C₁₈H₂₉N₃O₅S [ No CAS ]

References: [1]Angewandte Chemie - International Edition,2017,vol. 56,p. 248 - 253.
Angew. Chem.,2017,vol. 129,p. 254 - 259.

8
[ 313346-23-5 ]
5-[1-(2-cyanophenyl)piperidin-4-yl]sulfonyl}-2,4-dimethylbenzoic acid [ No CAS ]

References: [1]Patent: WO2018/89433,2018,A1 .

9
[ 313346-23-5 ]
2-[(3S)-4-(5-[(2S)-4-(2-cyanophenyl)-2-methylpiperazin-1-yl]methyl}-2,4-dimethylbenzenesulfonyl)-3-methylpiperazin-1-yl]pyridine-3-carbonitrile [ No CAS ]

References: [1]Patent: WO2018/89433,2018,A1 .

10
[ 313346-23-5 ]
(S)-2-(4-(5-(hydroxymethyl)-2,4-dimethylphenylsulfonyl)-3-methylpiperazin-1-yl)nicotinonitrile [ No CAS ]

References: [1]Patent: WO2018/89433,2018,A1 .

11
[ 313346-23-5 ]
(S)-2-(4-(5-formyl-2,4-dimethylphenylsulfonyl)-3-methylpiperazin-1-yl)nicotinonitrile [ No CAS ]

References: [1]Patent: WO2018/89433,2018,A1 .

12
[ 313346-23-5 ]
2-(4-(5-(4-(5-fluoropyridin-2-yl)piperazine-1-carbonyl)-2,4-dimethylphenylsulfonyl)piperazin-1-yl)benzonitrile [ No CAS ]

References: [1]Patent: WO2018/89433,2018,A1 .

13
[ 313346-23-5 ]
2-(4-(5-(4-(2-cyanophenyl)piperazin-1-ylsulfonyl)-2,4-dimethylbenzoyl)piperazin-1-yl)benzenesulfonamide [ No CAS ]

References: [1]Patent: WO2018/89433,2018,A1 .

14
[ 313346-23-5 ]
2-(4-(5-((4-(2-cyanophenyl)piperazin-1-yl)methyl)-2,4-dimethylphenylsulfonyl)piperazin-1-yl)benzonitrile [ No CAS ]

References: [1]Patent: WO2018/89433,2018,A1 .

15
[ 313346-23-5 ]
2-(4-(5-(hydroxymethyl)-2,4-dimethylphenylsulfonyl)piperazin-1-yl)benzonitrile [ No CAS ]

References: [1]Patent: WO2018/89433,2018,A1 .

16
[ 313346-23-5 ]
2-(4-(5-formyl-2,4-dimethylphenylsulfonyl)piperazin-1-yl)benzonitrile [ No CAS ]

References: [1]Patent: WO2018/89433,2018,A1 .

17
[ 313346-23-5 ]
C₂₉H₃₃FN₆O₂S [ No CAS ]

References: [1]Patent: WO2018/89433,2018,A1 .

18
[ 313346-23-5 ]
(5-(4-(5-fluoropyridin-2-yl)piperazin-1-ylsulfonyl)-2,4-dimethylphenyl)methanol [ No CAS ]

References: [1]Patent: WO2018/89433,2018,A1 .

19
[ 313346-23-5 ]
5-(4-(5-fluoropyridin-2-yl)piperazin-1-ylsulfonyl)-2,4-dimethylbenzaldehyde [ No CAS ]

References: [1]Patent: WO2018/89433,2018,A1 .

20
[ 313346-23-5 ]
2-(4-{5-[4-(2-cyanophenyl)piperazine-1-carbonyl]-2,4-dimethylbenzenesulfonyl}piperidin-1-yl)benzonitrile [ No CAS ]

References: [1]Patent: WO2018/89433,2018,A1 .

21
[ 863713-31-9 ]
[ 313346-23-5 ]
(S)-5-(4-(3-cyanopyridin-2-yl)-2-methylpiperazin-1-ylsulfonyl)-2,4-dimethylbenzoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In tetrahydrofuran; dichloromethane; for 3.0h;	To a solution of <strong>[313346-23-5]5-(chlorosulfonyl)-2,4-dimethylbenzoic acid</strong> (1.82 g, 7.4 mmol) in DCM (100 mL) was added Et3N (0.7 g, 7.4 mmol) and a solution of (S)-2-(3-methylpiperazin-1- yl)nicotinonitrile (3.0 g, 14.8 mmol) in THF (100 mL) dropwise at -78 C. The mixture was stirred at -78 C for 3 h. The solution was diluted with water (100 mL) and extracted with DCM (50 mL x 3). The organic phase was dried (Na2504), filtered, and concentrated in vacuo to give the crude product which was further purified by chromatography (silica, EtOAc/PE = 1/1) to afford (S)-5- (4-(3 -cyanopyridin-2-yl)-2-methylpiperazin- 1-yl sulfonyl)-2,4-dimethylb enzoic acid (0.92 g, 80%) as yellow oil (purity about 70%). ESI-MS (EI+, m/z: 415 [M+H].

References: [1]Patent: WO2018/89433,2018,A1 .Location in patent: Paragraph 00531.

22
[ 863713-31-9 ]
[ 313346-23-5 ]
2-[(3S)-4-{5-[(2S)-4-(3-cyanopyridin-2-yl)-2-methylpiperazine-1-carbonyl]-2,4-dimethylbenzenesulfonyl}-3-methylpiperazin-1-yl]pyridine-3-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
17%	With triethylamine; In tetrahydrofuran; dichloromethane; at -78℃; for 3.0h;	To a solution of (S)-2-(3-methylpiperazin-1-yl)nicotinonitrile (1.82 g, 7.4 mmol) in DCM (100 mL) was added TEA (704 mg, 7.4 mmol), and a solution of 5-(chlorosulfonyl)-2,4- dimethylbenzoic acid (3.0 g, 14.8 mmol) in THF dropwise at -78 C. The mixture was stirred at-78 C for 3 h, then diluted with water (100 mL) and extracted with DCM (100 mL x 3). Theorganic phases were washed with brine (50 mL x 3), dried (Na2SO4), filtered, and concentrated in vacuo. The crude product was purified by chromatography (silica, EtOAc/PE = 1/1) to afford 2-((S)-4-(5-((S)-4-(3-cyanopyridin-2-yl)-2-methylpiperazin- 1 -ylsulfonyl)-2,4-dimethylbenzoyl)-3-methylpiperazin-1-yl)nicotinonitrile 1-85 (760 mg, 1.27 mmol, 17%) as a white solid. ESI-MS (EI, m/z): 599 [M+H]t ‘HNMR(SOO IVIFIz, DMSO) 8.41-8.42 (m, 2H), 8.09-8.11 (m, 2H), 7.60-7.74 (m, 1H), 7.38-7.40 (m, 1H), 6.95-6.99 (m, 2H), 4.85 (s, 0.5H), 4.47 (s, 0.5H), 3.91-4.23 (m, 7H), 3.18-3.45 (m, 5H), 2.90-2.92 (m, 1H), 2.55 (s, 3H), 2.28 (s, 3H), 1.31-1.32 (m, 6H).

References: [1]Patent: WO2018/89433,2018,A1 .Location in patent: Paragraph 00543.

23
[ 907208-90-6 ]
[ 313346-23-5 ]
5-(4-(5-fluoropyridin-2-yl)piperazin-1-ylsulfonyl)-2,4-dimethylbenzoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With triethylamine; In dichloromethane; for 2.0h;	Et3N (513 mg, 5.08 mmol) was added to a mixture of 5-(chlorosulfonyl)-2,4- dimethylbenzoic acid (630 mg, 2.54 mmol) and 1-(5-fluoropyridin-2-yl)piperazine (475 mg, 2.54 mmol) in DCM (50 ml). The mixture was stirred at 25 C for 2 h, then the mixture was washed with brine, dried, and concentrated to afford 5-(4-(5-fluoropyridin-2-yl)piperazin-1-ylsulfonyl)- 2,4-dimethylbenzoic acid (900 mg, 2.29 mmol, 90%) as a yellow solid. ESI-MS (EI+, m/z):394.O[M+H]t

References: [1]Patent: WO2018/89433,2018,A1 .Location in patent: Paragraph 00645.

24
2-[(3S)-3-methylpiperazin-1-yl]benzonitrile [ No CAS ]
[ 313346-23-5 ]
2-((S)-4-(5-((S)-4-(2-cyanophenyl)-2-methylpiperazin-1-ylsulfonyl)-2,4-dimethylbenzoyl)-3-methylpiperazin-1-yl)benzonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
12%	With triethylamine; In tetrahydrofuran; dichloromethane; at -10℃; for 2.0h;	To a solution of (S)-2-(3-methylpiperazin-1-yl)benzonitrile (3.02 g, 15 mmol), TEA (1.52 g, 15 mmol) in DCM (50 mL) was added dropwise a solution of 5-(chlorosulfonyl)-2,4- dimethylbenzoic acid (1.86 g, 7.5 mmol) in THF (50 mL) at -10 C with stirring. The mixture was stirred at -10 C for 2 h, then concentrated and purified by prep-HPLC to afford 2-((5)-4-(5-((5)- 4-(2-cyanophenyl)-2-methyl-piperazin- 1 -yl sulfonyl)-2,4-dimethylb enzoyl)-3 -methylpiperazin- 1- yl)benzonitrile 1-90 (550 mg,0.92 mmol, 12%) as a white solid.j00478J ESI-MS (EI, m/z): 597.3 [M+H]t ‘H NMR (500 MHz, CDC13) 7.94-7.75 (m, 1H), 7.60 (t, J 7.5 Hz, 2H), 7.56-7.46 (m, 2H), 7.21 (s, 1H), 7.13-6.94 (m, 4H), 5.18-4.60 (m, 1H),4.15 (s, 1H), 3.93-3.23 (m, 8H), 3.19-2.68 (m, 4H), 2.60 (s, 3H), 2.39 (d, 3H), 1.60-1.42 (m, 6H).

References: [1]Patent: WO2018/89433,2018,A1 .Location in patent: Paragraph 00477.

25
2-[(3S)-3-methylpiperazin-1-yl]benzonitrile [ No CAS ]
[ 313346-23-5 ]
2-((S)-4-(5-(((S)-4-(2-cyanophenyl)-2-methylpiperazin-1-yl)methyl)-2,4-dimethylphenylsulfonyl)-3-methylpiperazin-1-yl)benzonitrile [ No CAS ]

References: [1]Patent: WO2018/89433,2018,A1 .

26
[ 313346-23-5 ]
[ 111373-03-6 ]
5-(4-(2-cyanophenyl)piperazin-1-ylsulfonyl)-2,4-dimethylbenzoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	With triethylamine; In dichloromethane; at 25℃; for 2.0h;	Et3N (202 mg, 2.0 mmol) was added to a solution of 5-(chlorosulfonyl)-2,4- dimethylbenzoic acid (250 mg, 1.0 mmol) and 2-(piperazin-1-yl)benzonitrile (187 mg, 1.0 mmol) in DCM (15 ml). The mixture was stirred at 25 C for 2 h, then the mixture was washed with water (15 mL) and concentrated to obtain the crude product. The crude product was purified by chromatography (silica, DCMIMeOH = 15/1) to afford 5 -(4-(2-cyanophenyl)piperazin- 1- ylsulfonyl)-2,4-dimethylbenzoic acid (220 mg, 0.55 mmol, 88%) as a yellow solid. ESI-MS (EI+, m/z): 400.2[M+H]t

References: [1]Patent: WO2018/89433,2018,A1 .Location in patent: Paragraph 00624.

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Technical Information

• Alkyl Halide Occurrence • Arndt-Eistert Homologation • Hunsdiecker-Borodin Reaction • Passerini Reaction • Preparation of Amines • Preparation of Carboxylic Acids • Reactions of Amines • Reactions of Benzene and Substituted Benzenes • Reactions of Carboxylic Acids • Schmidt Reaction • Specialized Acylation Reagents-Ketenes • Ugi Reaction

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H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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CAS No.: 313346-23-5

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CAS No.: 313346-23-5

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[ 313346-23-5 ] Synthesis Path-Downstream 1~26

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