Alternatived Products of [ 577752-97-7 ]
Product Details of [ 577752-97-7 ]
CAS No. : | 577752-97-7 |
MDL No. : | MFCD01107475 |
Formula : |
C13H17NO4S
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Boiling Point : |
- |
Linear Structure Formula : | - |
InChI Key : | - |
M.W : |
283.34
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Pubchem ID : | - |
Synonyms : |
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Safety of [ 577752-97-7 ]
Signal Word: | |
Class: | |
Precautionary Statements: | |
UN#: | |
Hazard Statements: | |
Packing Group: | |
Application In Synthesis of [ 577752-97-7 ]
* 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 [ 577752-97-7 ]
- 1
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[ 577752-97-7 ]
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[ 113-00-8 ]
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4-(1-Piperidylsulfonyl)benzoylguanidine hydrochloride
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
In methanol |
13 4-(1-Piperidylsulfonyl)benzoylguanidine hydrochloride
EXAMPLE 13 4-(1-Piperidylsulfonyl)benzoylguanidine hydrochloride is obtained analogously to the procedure given in Example 1 from methyl 4-(1-piperidylsulfonyl)benzoate and guanidine in methanol as reaction medium. White crystals, m.p. 281° C. |
- 2
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[ 1426243-57-3 ]
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[ 577752-97-7 ]
Yield | Reaction Conditions | Operation in experiment |
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Multi-step reaction with 2 steps
1: iron(III) chloride; sodium hydroxymethanesulfinate dihydrate / N,N-dimethyl-formamide; acetonitrile / 0.33 h / 20 °C
2: N-chloro-succinimide; triethylamine / 2.5 h / 0 - 23 °C |
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- 3
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[ 99768-12-4 ]
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[ 577752-97-7 ]
Yield | Reaction Conditions | Operation in experiment |
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Multi-step reaction with 3 steps
1.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 20 °C
1.2: 20 °C
2.1: iron(III) chloride; sodium hydroxymethanesulfinate dihydrate / N,N-dimethyl-formamide; acetonitrile / 0.33 h / 20 °C
3.1: N-chloro-succinimide; triethylamine / 2.5 h / 0 - 23 °C |
|
- 4
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[ 110-89-4 ]
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[ 69812-51-7 ]
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[ 577752-97-7 ]
Yield | Reaction Conditions | Operation in experiment |
95% |
With triethylamine In dichloromethane at 20℃; for 5h; Inert atmosphere; Cooling with ice; |
5.2.1. General procedure for the synthesis of intermediates 3a-nand 3p-y
General procedure: To a solution of sulphonyl chloride intermediate 1 (16.08 mmol)in anhydrousCH2Cl2(300 mL) was added the correspondingamines 2a-n, 3p-y (24.58 mmol) andEt3N(6.4 mL, 48.2 mmol)cooled with an ice bath. The reaction mixture was stirred at roomtemperature for 5 h under argon, then quenched with water(200 mL) and extracted withCH2Cl2(150 mL2). The combinedorganic phase was washed with 1 mol/L HCl (200 mL) and brine(200 mL) in turn. The obtained organic phase was dried overanhydrousNa2SO4,filtered and evaporated in vacuum to givecompounds 3a-n and 3p-y. |
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With triethylamine In dichloromethane for 1h; |
3.1.3.2 Synthesis of compound 4: 4-(piperidin-1-ylsulfonyl)benzoic acid
To a solution of 4-(chlorosulfonyl)phenyl acetate (2, 500mg, 2.14mmol) in anhydrous dichloromethane were added triethylamine (432mg, 4.28mmol) and piperidine (3, 200mg, 2.35mmol). The reaction mixture was stirred for an hour followed by removal of the solvent to obtain the crude sulfonamide intermediate methyl 4-(piperidin-1-ylsulfonyl)benzoate, which was suspended in water and filtered to remove the water soluble impurities, followed by dissolving the residue in 3:1 mixture of MeOH/THF. Lithium hydroxide (LiOH, 268mg, 6.4mmol) dissolved in 0.5mL of water was added to this solution and stirred for another 2h followed by removal of the solvent under vacuum. The residue was then dissolved in water and the solution was acidified using 3M HCl to precipitate the product which was purified by filtration to obtain compound 4 as white solid (511mg, yield=84%). |
Reference:
[1]Batt, Sarah M.; Besra, Gurdyal S.; Fu, Lei; Huang, Haihong; Li, Gang; Lu, Yu; Qin, Rongfei; Wang, Bin; Wang, Pengxu; Wang, Yanan; Wu, Chengwei
[European Journal of Medicinal Chemistry, 2022, vol. 231]
[2]Shukla, Nikunj M.; Chan, Michael; Lao, Fitzgerald S.; Chu, Paul J.; Belsuzarri, Masiel; Yao, Shiyin; Nan, Jason; Sato-Kaneko, Fumi; Saito, Tetsuya; Hayashi, Tomoko; Corr, Maripat; Carson, Dennis A.; Cottam, Howard B.
[Bioorganic and Medicinal Chemistry, 2021, vol. 43]
- 5
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[ 577752-97-7 ]
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4-(piperidin-1-ylsulfonyl)-N-(4-(o-tolyl)thiazol-2-yl)benzamide
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 2 steps
1: lithium hydroxide / methanol; tetrahydrofuran; water / 2 h
2: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; triethylamine / N,N-dimethyl-formamide / 16 h / 45 °C |
|
Reference:
[1]Shukla, Nikunj M.; Chan, Michael; Lao, Fitzgerald S.; Chu, Paul J.; Belsuzarri, Masiel; Yao, Shiyin; Nan, Jason; Sato-Kaneko, Fumi; Saito, Tetsuya; Hayashi, Tomoko; Corr, Maripat; Carson, Dennis A.; Cottam, Howard B.
[Bioorganic and Medicinal Chemistry, 2021, vol. 43]
- 6
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[ 577752-97-7 ]
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N-(4-(tert-butyl)thiazol-2-yl)-4-(piperidin-1-ylsulfonyl)benzamide
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 2 steps
1: lithium hydroxide / methanol; tetrahydrofuran; water / 2 h
2: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; triethylamine / N,N-dimethyl-formamide / 16 h / 45 °C |
|
Reference:
[1]Shukla, Nikunj M.; Chan, Michael; Lao, Fitzgerald S.; Chu, Paul J.; Belsuzarri, Masiel; Yao, Shiyin; Nan, Jason; Sato-Kaneko, Fumi; Saito, Tetsuya; Hayashi, Tomoko; Corr, Maripat; Carson, Dennis A.; Cottam, Howard B.
[Bioorganic and Medicinal Chemistry, 2021, vol. 43]
- 7
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[ 577752-97-7 ]
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N-(4-(2,3-dimethylphenyl)thiazol-2-yl)-4-(piperidin-1-ylsulfonyl)benzamide
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 2 steps
1: lithium hydroxide / methanol; tetrahydrofuran; water / 2 h
2: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 16 h / 45 °C |
|
Reference:
[1]Shukla, Nikunj M.; Chan, Michael; Lao, Fitzgerald S.; Chu, Paul J.; Belsuzarri, Masiel; Yao, Shiyin; Nan, Jason; Sato-Kaneko, Fumi; Saito, Tetsuya; Hayashi, Tomoko; Corr, Maripat; Carson, Dennis A.; Cottam, Howard B.
[Bioorganic and Medicinal Chemistry, 2021, vol. 43]
- 8
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[ 577752-97-7 ]
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N-(4-(2,4-dimethylphenyl)thiazol-2-yl)-4-(piperidin-1-ylsulfonyl)benzamide
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 2 steps
1: lithium hydroxide / methanol; tetrahydrofuran; water / 2 h
2: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 16 h / 45 °C |
|
Reference:
[1]Shukla, Nikunj M.; Chan, Michael; Lao, Fitzgerald S.; Chu, Paul J.; Belsuzarri, Masiel; Yao, Shiyin; Nan, Jason; Sato-Kaneko, Fumi; Saito, Tetsuya; Hayashi, Tomoko; Corr, Maripat; Carson, Dennis A.; Cottam, Howard B.
[Bioorganic and Medicinal Chemistry, 2021, vol. 43]
- 9
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[ 577752-97-7 ]
-
N-(4-(3,4-dimethylphenyl)thiazol-2-yl)-4-(piperidin-1-ylsulfonyl)benzamide
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 2 steps
1: lithium hydroxide / methanol; tetrahydrofuran; water / 2 h
2: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 16 h / 45 °C |
|
Reference:
[1]Shukla, Nikunj M.; Chan, Michael; Lao, Fitzgerald S.; Chu, Paul J.; Belsuzarri, Masiel; Yao, Shiyin; Nan, Jason; Sato-Kaneko, Fumi; Saito, Tetsuya; Hayashi, Tomoko; Corr, Maripat; Carson, Dennis A.; Cottam, Howard B.
[Bioorganic and Medicinal Chemistry, 2021, vol. 43]
- 10
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[ 577752-97-7 ]
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N-(4-(3,5-dimethylphenyl)thiazol-2-yl)-4-(piperidin-1-ylsulfonyl)benzamide
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 2 steps
1: lithium hydroxide / methanol; tetrahydrofuran; water / 2 h
2: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 16 h / 45 °C |
|
Reference:
[1]Shukla, Nikunj M.; Chan, Michael; Lao, Fitzgerald S.; Chu, Paul J.; Belsuzarri, Masiel; Yao, Shiyin; Nan, Jason; Sato-Kaneko, Fumi; Saito, Tetsuya; Hayashi, Tomoko; Corr, Maripat; Carson, Dennis A.; Cottam, Howard B.
[Bioorganic and Medicinal Chemistry, 2021, vol. 43]
- 11
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[ 577752-97-7 ]
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N-(4-(2,6-dimethylphenyl)thiazol-2-yl)-4-(piperidin-1-ylsulfonyl)benzamide
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 2 steps
1: lithium hydroxide / methanol; tetrahydrofuran; water / 2 h
2: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; triethylamine / N,N-dimethyl-formamide / 16 h / 45 °C |
|
Reference:
[1]Shukla, Nikunj M.; Chan, Michael; Lao, Fitzgerald S.; Chu, Paul J.; Belsuzarri, Masiel; Yao, Shiyin; Nan, Jason; Sato-Kaneko, Fumi; Saito, Tetsuya; Hayashi, Tomoko; Corr, Maripat; Carson, Dennis A.; Cottam, Howard B.
[Bioorganic and Medicinal Chemistry, 2021, vol. 43]
- 12
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[ 577752-97-7 ]
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N-(5-methyl-8H-indeno[1,2-d]thiazol-2-yl)-4-(piperidin-1-ylsulfonyl)benzamide
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 2 steps
1: lithium hydroxide / methanol; tetrahydrofuran; water / 2 h
2: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; triethylamine / N,N-dimethyl-formamide / 16 h / 45 °C |
|
Reference:
[1]Shukla, Nikunj M.; Chan, Michael; Lao, Fitzgerald S.; Chu, Paul J.; Belsuzarri, Masiel; Yao, Shiyin; Nan, Jason; Sato-Kaneko, Fumi; Saito, Tetsuya; Hayashi, Tomoko; Corr, Maripat; Carson, Dennis A.; Cottam, Howard B.
[Bioorganic and Medicinal Chemistry, 2021, vol. 43]
- 13
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[ 577752-97-7 ]
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N-(8-methyl-4,5-dihydronaphtho[1,2-d]thiazol-2-yl)-4-(piperidin-1-ylsulfonyl)benzamide
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 2 steps
1: lithium hydroxide / methanol; tetrahydrofuran; water / 2 h
2: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; triethylamine / N,N-dimethyl-formamide / 16 h / 45 °C |
|
Reference:
[1]Shukla, Nikunj M.; Chan, Michael; Lao, Fitzgerald S.; Chu, Paul J.; Belsuzarri, Masiel; Yao, Shiyin; Nan, Jason; Sato-Kaneko, Fumi; Saito, Tetsuya; Hayashi, Tomoko; Corr, Maripat; Carson, Dennis A.; Cottam, Howard B.
[Bioorganic and Medicinal Chemistry, 2021, vol. 43]
- 14
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[ 577752-97-7 ]
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4-(piperidin-1-ylsulfonyl)-N-(4-(m-tolyl)thiazol-2-yl)benzamide
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 2 steps
1: lithium hydroxide / methanol; tetrahydrofuran; water / 2 h
2: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; triethylamine / N,N-dimethyl-formamide / 16 h / 45 °C |
|
Reference:
[1]Shukla, Nikunj M.; Chan, Michael; Lao, Fitzgerald S.; Chu, Paul J.; Belsuzarri, Masiel; Yao, Shiyin; Nan, Jason; Sato-Kaneko, Fumi; Saito, Tetsuya; Hayashi, Tomoko; Corr, Maripat; Carson, Dennis A.; Cottam, Howard B.
[Bioorganic and Medicinal Chemistry, 2021, vol. 43]
- 15
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[ 577752-97-7 ]
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N-(4-(5-ethynyl-2-methylphenyl)thiazol-2-yl)-4-(piperidin-1-ylsulfonyl)benzamide
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 2 steps
1: lithium hydroxide / methanol; tetrahydrofuran; water / 2 h
2: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; triethylamine / N,N-dimethyl-formamide / 12 h / 45 °C |
|
Reference:
[1]Shukla, Nikunj M.; Chan, Michael; Lao, Fitzgerald S.; Chu, Paul J.; Belsuzarri, Masiel; Yao, Shiyin; Nan, Jason; Sato-Kaneko, Fumi; Saito, Tetsuya; Hayashi, Tomoko; Corr, Maripat; Carson, Dennis A.; Cottam, Howard B.
[Bioorganic and Medicinal Chemistry, 2021, vol. 43]
- 16
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[ 577752-97-7 ]
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N-(4-(5-ethyl-2-methylphenyl)thiazol-2-yl)-4-(piperidin-1-ylsulfonyl)benzamide
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 3 steps
1: lithium hydroxide / methanol; tetrahydrofuran; water / 2 h
2: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; triethylamine / N,N-dimethyl-formamide / 12 h / 45 °C
3: palladium on activated charcoal; hydrogen / methanol / 4 h / 2585.81 Torr |
|
Reference:
[1]Shukla, Nikunj M.; Chan, Michael; Lao, Fitzgerald S.; Chu, Paul J.; Belsuzarri, Masiel; Yao, Shiyin; Nan, Jason; Sato-Kaneko, Fumi; Saito, Tetsuya; Hayashi, Tomoko; Corr, Maripat; Carson, Dennis A.; Cottam, Howard B.
[Bioorganic and Medicinal Chemistry, 2021, vol. 43]
- 17
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[ 577752-97-7 ]
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N-(4-(2,5-dimethylphenyl)-1H-imidazol-2-yl)-4-(piperidin-1-ylsulfonyl)benzamide
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 2 steps
1: lithium hydroxide / methanol; tetrahydrofuran; water / 2 h
2: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; triethylamine / N,N-dimethyl-formamide / 12 h / 45 °C |
|
Reference:
[1]Shukla, Nikunj M.; Chan, Michael; Lao, Fitzgerald S.; Chu, Paul J.; Belsuzarri, Masiel; Yao, Shiyin; Nan, Jason; Sato-Kaneko, Fumi; Saito, Tetsuya; Hayashi, Tomoko; Corr, Maripat; Carson, Dennis A.; Cottam, Howard B.
[Bioorganic and Medicinal Chemistry, 2021, vol. 43]
- 18
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[ 577752-97-7 ]
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N-(6-(2,5-dimethylphenyl)pyridin-2-yl)-4-(piperidin-1-ylsulfonyl)benzamide
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 2 steps
1: lithium hydroxide / methanol; tetrahydrofuran; water / 2 h
2: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; triethylamine / N,N-dimethyl-formamide / 12 h / 45 °C |
|
Reference:
[1]Shukla, Nikunj M.; Chan, Michael; Lao, Fitzgerald S.; Chu, Paul J.; Belsuzarri, Masiel; Yao, Shiyin; Nan, Jason; Sato-Kaneko, Fumi; Saito, Tetsuya; Hayashi, Tomoko; Corr, Maripat; Carson, Dennis A.; Cottam, Howard B.
[Bioorganic and Medicinal Chemistry, 2021, vol. 43]
- 19
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[ 577752-97-7 ]
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N-(5-(2,5-dimethylphenyl)pyridin-2-yl)-4-(piperidin-1-ylsulfonyl)benzamide
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 2 steps
1: lithium hydroxide / methanol; tetrahydrofuran; water / 2 h
2: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; triethylamine / N,N-dimethyl-formamide / 12 h / 45 °C |
|
Reference:
[1]Shukla, Nikunj M.; Chan, Michael; Lao, Fitzgerald S.; Chu, Paul J.; Belsuzarri, Masiel; Yao, Shiyin; Nan, Jason; Sato-Kaneko, Fumi; Saito, Tetsuya; Hayashi, Tomoko; Corr, Maripat; Carson, Dennis A.; Cottam, Howard B.
[Bioorganic and Medicinal Chemistry, 2021, vol. 43]
- 20
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[ 577752-97-7 ]
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N-(6-(2,5-dimethylphenyl)pyridin-3-yl)-4-(piperidin-1-ylsulfonyl)benzamide
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 2 steps
1: lithium hydroxide / methanol; tetrahydrofuran; water / 2 h
2: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; triethylamine / N,N-dimethyl-formamide / 12 h / 45 °C |
|
|
Multi-step reaction with 2 steps
1: lithium hydroxide / methanol; tetrahydrofuran; water / 2 h
2: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 12 h / 45 °C |
|
Reference:
[1]Shukla, Nikunj M.; Chan, Michael; Lao, Fitzgerald S.; Chu, Paul J.; Belsuzarri, Masiel; Yao, Shiyin; Nan, Jason; Sato-Kaneko, Fumi; Saito, Tetsuya; Hayashi, Tomoko; Corr, Maripat; Carson, Dennis A.; Cottam, Howard B.
[Bioorganic and Medicinal Chemistry, 2021, vol. 43]
[2]Shukla, Nikunj M.; Chan, Michael; Lao, Fitzgerald S.; Chu, Paul J.; Belsuzarri, Masiel; Yao, Shiyin; Nan, Jason; Sato-Kaneko, Fumi; Saito, Tetsuya; Hayashi, Tomoko; Corr, Maripat; Carson, Dennis A.; Cottam, Howard B.
[Bioorganic and Medicinal Chemistry, 2021, vol. 43]
- 21
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[ 577752-97-7 ]
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N-(5-(2,5-dimethylphenyl)-1,3,4-thiadiazol-2-yl)-4-(piperidin-1-ylsulfonyl)benzamide
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 2 steps
1: lithium hydroxide / methanol; tetrahydrofuran; water / 2 h
2: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; triethylamine / N,N-dimethyl-formamide / 12 h / 45 °C |
|
Reference:
[1]Shukla, Nikunj M.; Chan, Michael; Lao, Fitzgerald S.; Chu, Paul J.; Belsuzarri, Masiel; Yao, Shiyin; Nan, Jason; Sato-Kaneko, Fumi; Saito, Tetsuya; Hayashi, Tomoko; Corr, Maripat; Carson, Dennis A.; Cottam, Howard B.
[Bioorganic and Medicinal Chemistry, 2021, vol. 43]
- 22
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[ 577752-97-7 ]
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N-(5-(diethylamino)-4-(2,5-dimethylphenyl)thiazol-2-yl)-4-(piperidin-1-ylsulfonyl)benzamide
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 2 steps
1: lithium hydroxide / methanol; tetrahydrofuran; water / 2 h
2: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 16 h / 45 °C |
|
Reference:
[1]Shukla, Nikunj M.; Chan, Michael; Lao, Fitzgerald S.; Chu, Paul J.; Belsuzarri, Masiel; Yao, Shiyin; Nan, Jason; Sato-Kaneko, Fumi; Saito, Tetsuya; Hayashi, Tomoko; Corr, Maripat; Carson, Dennis A.; Cottam, Howard B.
[Bioorganic and Medicinal Chemistry, 2021, vol. 43]
- 23
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[ 577752-97-7 ]
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N-(4-(2-bromo-5-methylphenyl)thiazol-2-yl)-4-(piperidin-1-ylsulfonyl)benzamide
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 2 steps
1: lithium hydroxide / methanol; tetrahydrofuran; water / 2 h
2: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; triethylamine / N,N-dimethyl-formamide / 16 h / 45 °C |
|
Reference:
[1]Shukla, Nikunj M.; Chan, Michael; Lao, Fitzgerald S.; Chu, Paul J.; Belsuzarri, Masiel; Yao, Shiyin; Nan, Jason; Sato-Kaneko, Fumi; Saito, Tetsuya; Hayashi, Tomoko; Corr, Maripat; Carson, Dennis A.; Cottam, Howard B.
[Bioorganic and Medicinal Chemistry, 2021, vol. 43]
- 24
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[ 577752-97-7 ]
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N-(4-(2,5-dimethylphenyl)-5-(piperidin-1-yl)thiazol-2-yl)-4-(piperidin-1-ylsulfonyl)benzamide
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 2 steps
1: lithium hydroxide / methanol; tetrahydrofuran; water / 2 h
2: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; triethylamine / N,N-dimethyl-formamide / 16 h / 45 °C |
|
Reference:
[1]Shukla, Nikunj M.; Chan, Michael; Lao, Fitzgerald S.; Chu, Paul J.; Belsuzarri, Masiel; Yao, Shiyin; Nan, Jason; Sato-Kaneko, Fumi; Saito, Tetsuya; Hayashi, Tomoko; Corr, Maripat; Carson, Dennis A.; Cottam, Howard B.
[Bioorganic and Medicinal Chemistry, 2021, vol. 43]
- 25
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[ 577752-97-7 ]
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N-(4-(2,5-dimethylphenyl)-5-phenylthiazol-2-yl)-4-(piperidin-1-ylsulfonyl)benzamide
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 2 steps
1: lithium hydroxide / methanol; tetrahydrofuran; water / 2 h
2: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 16 h / 45 °C |
|
Reference:
[1]Shukla, Nikunj M.; Chan, Michael; Lao, Fitzgerald S.; Chu, Paul J.; Belsuzarri, Masiel; Yao, Shiyin; Nan, Jason; Sato-Kaneko, Fumi; Saito, Tetsuya; Hayashi, Tomoko; Corr, Maripat; Carson, Dennis A.; Cottam, Howard B.
[Bioorganic and Medicinal Chemistry, 2021, vol. 43]
- 26
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[ 577752-97-7 ]
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N-(4-(2,5-dimethylphenyl)-5-(furan-2-yl)thiazol-2-yl)-4-(piperidin-1-ylsulfonyl)benzamide
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 2 steps
1: lithium hydroxide / methanol; tetrahydrofuran; water / 2 h
2: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 16 h / 45 °C |
|
Reference:
[1]Shukla, Nikunj M.; Chan, Michael; Lao, Fitzgerald S.; Chu, Paul J.; Belsuzarri, Masiel; Yao, Shiyin; Nan, Jason; Sato-Kaneko, Fumi; Saito, Tetsuya; Hayashi, Tomoko; Corr, Maripat; Carson, Dennis A.; Cottam, Howard B.
[Bioorganic and Medicinal Chemistry, 2021, vol. 43]
- 27
-
[ 577752-97-7 ]
-
N-(4-(2,5-dimethylphenyl)-5-(ethylthio)thiazol-2-yl)-4-(piperidin-1-ylsulfonyl)benzamide
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 2 steps
1: lithium hydroxide / methanol; tetrahydrofuran; water / 2 h
2: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 16 h / 45 °C |
|
Reference:
[1]Shukla, Nikunj M.; Chan, Michael; Lao, Fitzgerald S.; Chu, Paul J.; Belsuzarri, Masiel; Yao, Shiyin; Nan, Jason; Sato-Kaneko, Fumi; Saito, Tetsuya; Hayashi, Tomoko; Corr, Maripat; Carson, Dennis A.; Cottam, Howard B.
[Bioorganic and Medicinal Chemistry, 2021, vol. 43]
- 28
-
[ 577752-97-7 ]
-
N-(4-(2,5-dimethylphenyl)-5-ethoxythiazol-2-yl)-4-(piperidin-1-ylsulfonyl)benzamide
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 2 steps
1: lithium hydroxide / methanol; tetrahydrofuran; water / 2 h
2: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 16 h / 45 °C |
|
Reference:
[1]Shukla, Nikunj M.; Chan, Michael; Lao, Fitzgerald S.; Chu, Paul J.; Belsuzarri, Masiel; Yao, Shiyin; Nan, Jason; Sato-Kaneko, Fumi; Saito, Tetsuya; Hayashi, Tomoko; Corr, Maripat; Carson, Dennis A.; Cottam, Howard B.
[Bioorganic and Medicinal Chemistry, 2021, vol. 43]
- 29
-
[ 577752-97-7 ]
-
N-(4-(2,5-dimethylphenyl)-5-methylthiazol-2-yl)-4-(piperidin-1-ylsulfonyl)benzamide
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 2 steps
1: lithium hydroxide / methanol; tetrahydrofuran; water / 2 h
2: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; triethylamine / N,N-dimethyl-formamide / 16 h / 45 °C |
|
Reference:
[1]Shukla, Nikunj M.; Chan, Michael; Lao, Fitzgerald S.; Chu, Paul J.; Belsuzarri, Masiel; Yao, Shiyin; Nan, Jason; Sato-Kaneko, Fumi; Saito, Tetsuya; Hayashi, Tomoko; Corr, Maripat; Carson, Dennis A.; Cottam, Howard B.
[Bioorganic and Medicinal Chemistry, 2021, vol. 43]
- 30
-
[ 577752-97-7 ]
-
N-(5-bromo-4-(2,5-dimethylphenyl)thiazol-2-yl)-4-(piperidin-1-ylsulfonyl)benzamide
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 2 steps
1: lithium hydroxide / methanol; tetrahydrofuran; water / 2 h
2: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; triethylamine / N,N-dimethyl-formamide / 16 h / 45 °C |
|
Reference:
[1]Shukla, Nikunj M.; Chan, Michael; Lao, Fitzgerald S.; Chu, Paul J.; Belsuzarri, Masiel; Yao, Shiyin; Nan, Jason; Sato-Kaneko, Fumi; Saito, Tetsuya; Hayashi, Tomoko; Corr, Maripat; Carson, Dennis A.; Cottam, Howard B.
[Bioorganic and Medicinal Chemistry, 2021, vol. 43]
- 31
-
[ 577752-97-7 ]
-
N-(4-(2,5-dimethylphenyl)-5-ethynylthiazol-2-yl)-4-(piperidin-1-ylsulfonyl)benzamide
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 3 steps
1: lithium hydroxide / methanol; tetrahydrofuran; water / 2 h
2: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; triethylamine / N,N-dimethyl-formamide / 16 h / 45 °C
3: tetrakis(triphenylphosphine) palladium(0); copper(l) iodide; diethylamine / N,N-dimethyl-formamide / 2 h / 100 °C / Inert atmosphere; Microwave irradiation |
|
Reference:
[1]Shukla, Nikunj M.; Chan, Michael; Lao, Fitzgerald S.; Chu, Paul J.; Belsuzarri, Masiel; Yao, Shiyin; Nan, Jason; Sato-Kaneko, Fumi; Saito, Tetsuya; Hayashi, Tomoko; Corr, Maripat; Carson, Dennis A.; Cottam, Howard B.
[Bioorganic and Medicinal Chemistry, 2021, vol. 43]
- 32
-
[ 577752-97-7 ]
-
N-(5-(but-1-yn-1-yl)-4-(2,5-dimethylphenyl)thiazol-2-yl)-4-(piperidin-1-ylsulfonyl)benzamide
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 3 steps
1: lithium hydroxide / methanol; tetrahydrofuran; water / 2 h
2: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; triethylamine / N,N-dimethyl-formamide / 16 h / 45 °C
3: diisopropylamine; tetrakis(triphenylphosphine) palladium(0); copper(l) iodide / N,N-dimethyl-formamide / 2 h / 100 °C / Inert atmosphere; Microwave irradiation |
|
Reference:
[1]Shukla, Nikunj M.; Chan, Michael; Lao, Fitzgerald S.; Chu, Paul J.; Belsuzarri, Masiel; Yao, Shiyin; Nan, Jason; Sato-Kaneko, Fumi; Saito, Tetsuya; Hayashi, Tomoko; Corr, Maripat; Carson, Dennis A.; Cottam, Howard B.
[Bioorganic and Medicinal Chemistry, 2021, vol. 43]
- 33
-
[ 577752-97-7 ]
-
N-(4-(2,5-dimethylphenyl)-5-(pent-1-yn-1-yl)thiazol-2-yl)-4-(piperidin-1-ylsulfonyl)benzamide
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 3 steps
1: lithium hydroxide / methanol; tetrahydrofuran; water / 2 h
2: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; triethylamine / N,N-dimethyl-formamide / 16 h / 45 °C
3: diisopropylamine; tetrakis(triphenylphosphine) palladium(0); copper(l) iodide / N,N-dimethyl-formamide / 2 h / 100 °C / Inert atmosphere; Microwave irradiation |
|
Reference:
[1]Shukla, Nikunj M.; Chan, Michael; Lao, Fitzgerald S.; Chu, Paul J.; Belsuzarri, Masiel; Yao, Shiyin; Nan, Jason; Sato-Kaneko, Fumi; Saito, Tetsuya; Hayashi, Tomoko; Corr, Maripat; Carson, Dennis A.; Cottam, Howard B.
[Bioorganic and Medicinal Chemistry, 2021, vol. 43]
- 34
-
[ 577752-97-7 ]
-
N-(4-(5-bromo-2-methylphenyl)thiazol-2-yl)-4-(piperidin-1-ylsulfonyl)benzamide
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 2 steps
1: lithium hydroxide / methanol; tetrahydrofuran; water / 2 h
2: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; triethylamine / N,N-dimethyl-formamide / 16 h / 45 °C |
|
Reference:
[1]Shukla, Nikunj M.; Chan, Michael; Lao, Fitzgerald S.; Chu, Paul J.; Belsuzarri, Masiel; Yao, Shiyin; Nan, Jason; Sato-Kaneko, Fumi; Saito, Tetsuya; Hayashi, Tomoko; Corr, Maripat; Carson, Dennis A.; Cottam, Howard B.
[Bioorganic and Medicinal Chemistry, 2021, vol. 43]
- 35
-
[ 577752-97-7 ]
-
N-(4-(2,5-dimethylphenyl)-5-ethylthiazol-2-yl)-4-(piperidin-1-ylsulfonyl)benzamide
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 4 steps
1: lithium hydroxide / methanol; tetrahydrofuran; water / 2 h
2: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; triethylamine / N,N-dimethyl-formamide / 16 h / 45 °C
3: tetrakis(triphenylphosphine) palladium(0); copper(l) iodide; diethylamine / N,N-dimethyl-formamide / 2 h / 100 °C / Inert atmosphere; Microwave irradiation
4: palladium on activated charcoal; hydrogen / methanol / 6 h / 2585.81 Torr |
|
Reference:
[1]Shukla, Nikunj M.; Chan, Michael; Lao, Fitzgerald S.; Chu, Paul J.; Belsuzarri, Masiel; Yao, Shiyin; Nan, Jason; Sato-Kaneko, Fumi; Saito, Tetsuya; Hayashi, Tomoko; Corr, Maripat; Carson, Dennis A.; Cottam, Howard B.
[Bioorganic and Medicinal Chemistry, 2021, vol. 43]
- 36
-
[ 577752-97-7 ]
-
N-(5-butyl-4-(2,5-dimethylphenyl)thiazol-2-yl)-4-(piperidin-1-ylsulfonyl)benzamide
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 4 steps
1: lithium hydroxide / methanol; tetrahydrofuran; water / 2 h
2: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; triethylamine / N,N-dimethyl-formamide / 16 h / 45 °C
3: diisopropylamine; tetrakis(triphenylphosphine) palladium(0); copper(l) iodide / N,N-dimethyl-formamide / 2 h / 100 °C / Inert atmosphere; Microwave irradiation
4: palladium on activated charcoal; hydrogen / methanol / 6 h / 2585.81 Torr |
|
Reference:
[1]Shukla, Nikunj M.; Chan, Michael; Lao, Fitzgerald S.; Chu, Paul J.; Belsuzarri, Masiel; Yao, Shiyin; Nan, Jason; Sato-Kaneko, Fumi; Saito, Tetsuya; Hayashi, Tomoko; Corr, Maripat; Carson, Dennis A.; Cottam, Howard B.
[Bioorganic and Medicinal Chemistry, 2021, vol. 43]
- 37
-
[ 577752-97-7 ]
-
N-(4-(2,5-dimethylphenyl)-5-pentylthiazol-2-yl)-4-(piperidin-1-ylsulfonyl)benzamide
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 4 steps
1: lithium hydroxide / methanol; tetrahydrofuran; water / 2 h
2: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; triethylamine / N,N-dimethyl-formamide / 16 h / 45 °C
3: diisopropylamine; tetrakis(triphenylphosphine) palladium(0); copper(l) iodide / N,N-dimethyl-formamide / 2 h / 100 °C / Inert atmosphere; Microwave irradiation
4: palladium on activated charcoal; hydrogen / methanol / 6 h / 2585.81 Torr |
|
Reference:
[1]Shukla, Nikunj M.; Chan, Michael; Lao, Fitzgerald S.; Chu, Paul J.; Belsuzarri, Masiel; Yao, Shiyin; Nan, Jason; Sato-Kaneko, Fumi; Saito, Tetsuya; Hayashi, Tomoko; Corr, Maripat; Carson, Dennis A.; Cottam, Howard B.
[Bioorganic and Medicinal Chemistry, 2021, vol. 43]
- 38
-
[ 577752-97-7 ]
-
N-(4-(2,5-dimethylphenyl)thiazol-2-yl)-N-methyl-4-(piperidin-1-ylsulfonyl)benzamide
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 3 steps
1: lithium hydroxide / methanol; tetrahydrofuran; water / 2 h
2: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; triethylamine / N,N-dimethyl-formamide / 16 h / 45 °C
3: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1 h |
|
Reference:
[1]Shukla, Nikunj M.; Chan, Michael; Lao, Fitzgerald S.; Chu, Paul J.; Belsuzarri, Masiel; Yao, Shiyin; Nan, Jason; Sato-Kaneko, Fumi; Saito, Tetsuya; Hayashi, Tomoko; Corr, Maripat; Carson, Dennis A.; Cottam, Howard B.
[Bioorganic and Medicinal Chemistry, 2021, vol. 43]
- 39
-
[ 577752-97-7 ]
-
N-(4-(2,5-dimethylbenzyl)thiazol-2-yl)-4-(piperidin-1-ylsulfonyl)benzamide
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 2 steps
1: lithium hydroxide / methanol; tetrahydrofuran; water / 2 h
2: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; triethylamine / N,N-dimethyl-formamide / 16 h / 45 °C |
|
Reference:
[1]Shukla, Nikunj M.; Chan, Michael; Lao, Fitzgerald S.; Chu, Paul J.; Belsuzarri, Masiel; Yao, Shiyin; Nan, Jason; Sato-Kaneko, Fumi; Saito, Tetsuya; Hayashi, Tomoko; Corr, Maripat; Carson, Dennis A.; Cottam, Howard B.
[Bioorganic and Medicinal Chemistry, 2021, vol. 43]
- 40
-
[ 577752-97-7 ]
-
N-(4-(2,5-dimethylphenyl)thiazol-2-yl)-4-(piperidin-1-ylsulfonyl)-N-(prop-2-yn-1-yl)benzamide
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 3 steps
1: lithium hydroxide / methanol; tetrahydrofuran; water / 2 h
2: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; triethylamine / N,N-dimethyl-formamide / 16 h / 45 °C
3: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1 h |
|
Reference:
[1]Shukla, Nikunj M.; Chan, Michael; Lao, Fitzgerald S.; Chu, Paul J.; Belsuzarri, Masiel; Yao, Shiyin; Nan, Jason; Sato-Kaneko, Fumi; Saito, Tetsuya; Hayashi, Tomoko; Corr, Maripat; Carson, Dennis A.; Cottam, Howard B.
[Bioorganic and Medicinal Chemistry, 2021, vol. 43]
- 41
-
[ 577752-97-7 ]
-
N-(4-methylthiazol-2-yl)-4-(piperidin-1-ylsulfonyl)benzamide
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 2 steps
1: lithium hydroxide / methanol; tetrahydrofuran; water / 2 h
2: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; triethylamine / N,N-dimethyl-formamide / 16 h / 45 °C |
|
Reference:
[1]Shukla, Nikunj M.; Chan, Michael; Lao, Fitzgerald S.; Chu, Paul J.; Belsuzarri, Masiel; Yao, Shiyin; Nan, Jason; Sato-Kaneko, Fumi; Saito, Tetsuya; Hayashi, Tomoko; Corr, Maripat; Carson, Dennis A.; Cottam, Howard B.
[Bioorganic and Medicinal Chemistry, 2021, vol. 43]
- 42
-
[ 577752-97-7 ]
-
N-(4-ethylthiazol-2-yl)-4-(piperidin-1-ylsulfonyl)benzamide
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 2 steps
1: lithium hydroxide / methanol; tetrahydrofuran; water / 2 h
2: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; triethylamine / N,N-dimethyl-formamide / 16 h / 45 °C |
|
Reference:
[1]Shukla, Nikunj M.; Chan, Michael; Lao, Fitzgerald S.; Chu, Paul J.; Belsuzarri, Masiel; Yao, Shiyin; Nan, Jason; Sato-Kaneko, Fumi; Saito, Tetsuya; Hayashi, Tomoko; Corr, Maripat; Carson, Dennis A.; Cottam, Howard B.
[Bioorganic and Medicinal Chemistry, 2021, vol. 43]
- 43
-
[ 577752-97-7 ]
-
4-(piperidin-1-ylsulfonyl)-N-(4-propylthiazol-2-yl)benzamide
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 2 steps
1: lithium hydroxide / methanol; tetrahydrofuran; water / 2 h
2: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; triethylamine / N,N-dimethyl-formamide / 16 h / 45 °C |
|
Reference:
[1]Shukla, Nikunj M.; Chan, Michael; Lao, Fitzgerald S.; Chu, Paul J.; Belsuzarri, Masiel; Yao, Shiyin; Nan, Jason; Sato-Kaneko, Fumi; Saito, Tetsuya; Hayashi, Tomoko; Corr, Maripat; Carson, Dennis A.; Cottam, Howard B.
[Bioorganic and Medicinal Chemistry, 2021, vol. 43]
- 44
-
[ 577752-97-7 ]
-
[ 10252-83-2 ]
Yield | Reaction Conditions | Operation in experiment |
95% |
With lithium hydroxide monohydrate In methanol; water at 20℃; for 2h; |
5.2.2. General procedure for the synthesis of intermediates 4a-y
General procedure: To a solution of 3a-n, p-y or 5 (14.12 mmol) inCH3OH(100 mL)was added 1 mol/L LiOH aqueous solution (42.4 mL). The reactionmixture was stirred at room temperature for 2 h, then evaporatedin vacuo. The residue was diluted withH2Oand the aqueous solutionwas acidified with 6 mol/L HCl to pH6e7. The precipitatedsolid was filtered to afford compounds 4a-y. |
511 mg |
With lithium hydroxide In tetrahydrofuran; methanol; water for 2h; |
3.1.3.2 Synthesis of compound 4: 4-(piperidin-1-ylsulfonyl)benzoic acid
To a solution of 4-(chlorosulfonyl)phenyl acetate (2, 500mg, 2.14mmol) in anhydrous dichloromethane were added triethylamine (432mg, 4.28mmol) and piperidine (3, 200mg, 2.35mmol). The reaction mixture was stirred for an hour followed by removal of the solvent to obtain the crude sulfonamide intermediate methyl 4-(piperidin-1-ylsulfonyl)benzoate, which was suspended in water and filtered to remove the water soluble impurities, followed by dissolving the residue in 3:1 mixture of MeOH/THF. Lithium hydroxide (LiOH, 268mg, 6.4mmol) dissolved in 0.5mL of water was added to this solution and stirred for another 2h followed by removal of the solvent under vacuum. The residue was then dissolved in water and the solution was acidified using 3M HCl to precipitate the product which was purified by filtration to obtain compound 4 as white solid (511mg, yield=84%). |
Reference:
[1]Batt, Sarah M.; Besra, Gurdyal S.; Fu, Lei; Huang, Haihong; Li, Gang; Lu, Yu; Qin, Rongfei; Wang, Bin; Wang, Pengxu; Wang, Yanan; Wu, Chengwei
[European Journal of Medicinal Chemistry, 2022, vol. 231]
[2]Shukla, Nikunj M.; Chan, Michael; Lao, Fitzgerald S.; Chu, Paul J.; Belsuzarri, Masiel; Yao, Shiyin; Nan, Jason; Sato-Kaneko, Fumi; Saito, Tetsuya; Hayashi, Tomoko; Corr, Maripat; Carson, Dennis A.; Cottam, Howard B.
[Bioorganic and Medicinal Chemistry, 2021, vol. 43]
- 45
-
[ 577752-97-7 ]
-
methyl {2-[4-(piperidin-1-yl-sulfonyl)benzamide]thiophene-3-carbonyl}carbamate
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 2 steps
1: lithium hydroxide monohydrate / methanol; water / 2 h / 20 °C
2: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 12 h / 20 °C |
|
Reference:
[1]Batt, Sarah M.; Besra, Gurdyal S.; Fu, Lei; Huang, Haihong; Li, Gang; Lu, Yu; Qin, Rongfei; Wang, Bin; Wang, Pengxu; Wang, Yanan; Wu, Chengwei
[European Journal of Medicinal Chemistry, 2022, vol. 231]
- 46
-
[ 577752-97-7 ]
-
2-(4-(piperidine-1-sulfonyl)benzamido)thiophene-3-carbonylcarbamic acid propyl ester
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 2 steps
1: lithium hydroxide monohydrate / methanol; water / 2 h / 20 °C
2: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 12 h / 20 °C |
|
Reference:
[1]Batt, Sarah M.; Besra, Gurdyal S.; Fu, Lei; Huang, Haihong; Li, Gang; Lu, Yu; Qin, Rongfei; Wang, Bin; Wang, Pengxu; Wang, Yanan; Wu, Chengwei
[European Journal of Medicinal Chemistry, 2022, vol. 231]
- 47
-
[ 577752-97-7 ]
-
2,2,2-trifluoroethyl (2-(4-(piperidin-1-ylsulfonyl)benzamido)thiophene-3-carbonyl)carbamate
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 2 steps
1: lithium hydroxide monohydrate / methanol; water / 2 h / 20 °C
2: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 12 h / 20 °C |
|
Reference:
[1]Batt, Sarah M.; Besra, Gurdyal S.; Fu, Lei; Huang, Haihong; Li, Gang; Lu, Yu; Qin, Rongfei; Wang, Bin; Wang, Pengxu; Wang, Yanan; Wu, Chengwei
[European Journal of Medicinal Chemistry, 2022, vol. 231]
- 48
-
[ 577752-97-7 ]
-
2-(4-(piperidin-1-ylsulfonyl)benzamido)-N-(pyridin-2-yl)thiophene-3-carboxamide
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 2 steps
1: lithium hydroxide monohydrate / methanol; water / 2 h / 20 °C
2: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 12 h / 20 °C |
|
Reference:
[1]Batt, Sarah M.; Besra, Gurdyal S.; Fu, Lei; Huang, Haihong; Li, Gang; Lu, Yu; Qin, Rongfei; Wang, Bin; Wang, Pengxu; Wang, Yanan; Wu, Chengwei
[European Journal of Medicinal Chemistry, 2022, vol. 231]
- 49
-
[ 577752-97-7 ]
-
N-(4-methylpyrimidin-2-yl)-2-(4-(piperidin-1-ylsulfonyl)benzamido)thiophene-3-carboxamide
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 2 steps
1: lithium hydroxide monohydrate / methanol; water / 2 h / 20 °C
2: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 12 h / 20 °C |
|
Reference:
[1]Batt, Sarah M.; Besra, Gurdyal S.; Fu, Lei; Huang, Haihong; Li, Gang; Lu, Yu; Qin, Rongfei; Wang, Bin; Wang, Pengxu; Wang, Yanan; Wu, Chengwei
[European Journal of Medicinal Chemistry, 2022, vol. 231]
- 50
-
[ 577752-97-7 ]
-
2-(4-(piperidine-1-sulfonyl)benzamido)thiophene-3-carbonylcarbamic acid ethyl ester
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 2 steps
1: lithium hydroxide monohydrate / methanol; water / 2 h / 20 °C
2: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 12 h / 20 °C |
|
Reference:
[1]Batt, Sarah M.; Besra, Gurdyal S.; Fu, Lei; Huang, Haihong; Li, Gang; Lu, Yu; Qin, Rongfei; Wang, Bin; Wang, Pengxu; Wang, Yanan; Wu, Chengwei
[European Journal of Medicinal Chemistry, 2022, vol. 231]