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[ CAS No. 63353-34-4 ] {[proInfo.proName]}

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Chemical Structure| 63353-34-4
Chemical Structure| 63353-34-4
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Product Details of [ 63353-34-4 ]

CAS No. :63353-34-4 MDL No. :MFCD12783397
Formula : C9H19ClO2S Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 226.76 Pubchem ID :-
Synonyms :

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Application In Synthesis of [ 63353-34-4 ]

* 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 [ 63353-34-4 ]

[ 63353-34-4 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 35192-74-6 ]
  • [ 63353-34-4 ]
Reference： [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 5145 - 5149
  • 2
  • [ 480-91-1 ]
  • [ 63353-34-4 ]
  • [ 1204347-73-8 ]
YieldReaction ConditionsOperation in experiment
With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃;
Stage #1: oxisoindole With sodium hydride In N,N-dimethyl-formamide at 0℃; Stage #2: n-nonylsulfonyl chloride In N,N-dimethyl-formamide at 20℃; 2 1.5 mmol 6 was added to DMF (8 mL), and the solution was cooled to 0 0C. NaH (1.65 mmol) was added, followed by the sulfonyl chloride (1.8 mmol), and the mixture was stirred and allowed to warm to room temperature. Reaction progress was monitored by TLC (25% MeOH in CHCl3). When complete, saturated ammonium chloride solution was added (80 mL), the product was extracted with EtOAc (3 x 20 mL), dried over MgSO4, and evaporated in vacuo. The product was purified by flash chromatography (2% MeOH in CHCl3).
Reference： [1]Location in patent: experimental part Wydysh, Edward A.; Medghalchi, Susan M.; Vadlamudi, Aravinda; Townsendd, Craig A. [Journal of Medicinal Chemistry, 2009, vol. 52, # 10, p. 3317 - 3327]
[2]Current Patent Assignee: FAS SECURED CREDITORS HOLDCO - WO2010/5922, 2010, A1 Location in patent: Page/Page column 28, Fig 2
  • 3
  • [ 63353-34-4 ]
  • [ 55279-30-6 ]
  • methyl 3-(nonylsulfonamido)isonicotinate [ No CAS ]
YieldReaction ConditionsOperation in experiment
21% Stage #1: n-nonylsulfonyl chloride; methyl 3-aminoisonicotinate With triethylamine In dichloromethane at 20℃; Stage #2: With potassium carbonate In methanol 1.7.1 [00256] Step-1: methyl 3-(nonylsulfonamido)isonicotinate To a solution of methyl 3-aminopicolinate (100 mg, 0.65 mmol) and nonylsulfonyl chloride (146 mg, 0.65 mmol) in DCM (2 ml), TEA (0.46 ml, 3.2 mmol) was added drop-wise and stirred at room temperature. After completion of reaction as indicated by TLC, reaction mixture was quenched with 1N HCl and extracted with DCM (3x10 ml). The combined organic layer was dried over anhydrous sodium sulphate and evaporated under vacuum. The mixture of the product was dissolved in MeOH (3 ml) and treated with K2CO3 (150 mg). The conversion of bis-sulfonamide to monosulfonamide was monitored by TLC. The solvent was removed under vacuum and quenched with water. The product was extracted with ethyl acetate (3x 10 ml). The combined organic layer was evaporated and the crude was purified by silica gel column chromatography (20 % Ethyl acetate/Hexane) to obtain methyl 3-(nonylsulfonamido)isonicotinate (47 mg, 21 %). 1H NMR (400 MHz, DMSO-d6) d 9.75 (s, 1H), 8.79 (s, 1H), 8.50 (d, J = 5.0 Hz, 1H), 7.72 (d, J = 5.0 Hz, 1H), 3.89 (s, 3H), 3.31 - 3.26 (m, 2H), 1.74 - 1.57 (m, 2H), 1.40 - 1.10 (m, 12H), 0.84 (t, J = 6.8 Hz, 3H). MS observed: 342.30(M+H).
Reference： [1]Current Patent Assignee: STANFORD UNIVERSITY - WO2021/35031, 2021, A1 Location in patent: Paragraph 00256
  • 4
  • [ 63353-34-4 ]
  • [ 55279-30-6 ]
  • 3-(nonylsulfonamido)isonicotinic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
13% Stage #1: n-nonylsulfonyl chloride; methyl 3-aminoisonicotinate With triethylamine In dichloromethane at 20℃; Stage #2: With sodium hydroxide In methanol at 20℃; 1.7.2 [00257] Step-2: 3-(nonylsulfonamido)isonicotinic acid: To a solution of methyl 3- aminopicolinate (200 mg, 1.3 mmol) and nonylsulfonyl chloride (296 mg, 1.3 mmol) in DCM (4 ml), TEA (0.85 ml, 6.3 mmol) was added drop-wise and stirred at room temperature. After completion of reaction as indicated by TLC, reaction mixture was quenched with 1N HCl and extracted with DCM (3x10 ml). The combined organic layer was dried over anhydrous sodium sulphate and evaporated under vacuum. The mixture of R5-0022 and R5-0022-A was dissolved in MeOH (3 ml) and added into 1N NaOH (1 ml). The resulting mixture was stirred at room temperature. After completion of reaction as indicated by TLC, The solvent was removed and quenched with 1N HCl. The solid was filtered and washed with water. The crude was triturated with diethyl ether to obtain title compound as brown solid (56 mg, 13 %). 1H NMR (400 MHz, DMSO-d6) d 8.81 (s, 1H), 8.41 (d, J = 5.0 Hz, 1H), 7.79 (d, J = 4.9 Hz, 1H), 3.30-3.35(m, 2H), 1.74 - 1.44 (m, 2H), 1.38 - 1.10 (m, 12H), 0.84 (t, J = 6.5 Hz, 3H). MS observed: 329.2(M+H).
Reference： [1]Current Patent Assignee: STANFORD UNIVERSITY - WO2021/35031, 2021, A1 Location in patent: Paragraph 00257

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