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[ CAS No. 83922-54-7 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 83922-54-7
Chemical Structure| 83922-54-7
Chemical Structure| 83922-54-7
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Product Details of [ 83922-54-7 ]

CAS No. :83922-54-7 MDL No. :MFCD11052340
Formula : C8H9NO3S Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 199.23 Pubchem ID :-
Synonyms :
Chemical Name :4-(Methylsulfonamido)benzaldehyde

Calculated chemistry of [ 83922-54-7 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.12
Num. rotatable bonds : 3
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 50.1
TPSA : 71.62 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.03 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.63
Log Po/w (XLOGP3) : 0.68
Log Po/w (WLOGP) : 1.76
Log Po/w (MLOGP) : 0.03
Log Po/w (SILICOS-IT) : 0.51
Consensus Log Po/w : 0.72

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.65
Solubility : 4.49 mg/ml ; 0.0225 mol/l
Class : Very soluble
Log S (Ali) : -1.76
Solubility : 3.46 mg/ml ; 0.0173 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.71
Solubility : 0.384 mg/ml ; 0.00193 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.38

Safety of [ 83922-54-7 ]

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 [ 83922-54-7 ]

* 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 [ 83922-54-7 ]

[ 83922-54-7 ] Synthesis Path-Downstream   1~54

  • 2
  • [ 83922-54-7 ]
  • [ 152122-41-3 ]
  • 4-(4-Fluorophenyl)-2-(4-methanesulfonamidophenyl)-5-(pyridin-4-yl)-1H-imidazole [ No CAS ]
  • 3
  • [ 83922-54-7 ]
  • [ 152153-01-0 ]
  • N-[4-((3aS,10R)-1-Oxo-3a,4,9,10-tetrahydro-3H-2-oxa-9,10a-diaza-cyclopenta[b]fluoren-10-yl)-phenyl]-methanesulfonamide [ No CAS ]
  • 4
  • [ 83922-54-7 ]
  • [ 650628-65-2 ]
  • N-[4-((E)-{2-[1-(3-methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-yl]hydrazono}methyl)phenyl]methanesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
92% With pyrrolidine; In ethanol; at 100℃; for 21h; A mixture of 4-hydrazino-1-(3-methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidine (Intermediates Example T) (43 mg, 0.167 [MMOL),] [N- (4-] formylphenyl) methanesulfonamide (40 mg 0.201 [MMOL)] and pyrrolidine (2 drops) in ethanol (10 mL) was heated to [100 C] for 21 h. The reaction was then cooled to RT, the solid collected by filtration, and washed with ethanol and ether to provide product as a white solid (67 mg, 92% yield). ['H] NMR (400 MHz, DMSO) [8] 12.22 (s, [1 H),] 10.08 (s, [1 H),] 8.66 (s, 1H), 8.47 (s, [1 H),] 8.24 (s, 1 H), 7.82 (m, 4H), 7.47 (t, [1] H), 7.31 (d, 2H), 6.94 (d, [1] H), 3.83 (s, [3H),] 3.06 (s, [3H)] ppm; ES-MS m/z 438 (MH+).
  • 5
  • 4-(1,3-dioxolan-2-yl)benzenamine [ No CAS ]
  • [ 83922-54-7 ]
  • 6
  • [ 1826-67-1 ]
  • [ 83922-54-7 ]
  • [ 863029-84-9 ]
YieldReaction ConditionsOperation in experiment
A solution of 4-methanesulfonyl benzaldehyde (834 mg, 4.19 mmol) in 13 mL of THF was added to 8.5 mL of 1.0 M (H2C=CH2) MgBr in THF. The resulting suspension was stirred for 3.5 h and then quenched with 10 mL of saturated NH4Cl solution. The solution was extracted with diethyl ether (2 x 20 mL) and separated. The combined organic extracts were washed with water and saturated NaCI solution. After drying over MgS04, the solution was evaporated to give 4-MeSO2N (H) C6H4 [C (H) (OH) (CH=CH2)] as an orange liquid (1.036 g).
  • 7
  • [ 100-44-7 ]
  • [ 83922-54-7 ]
  • [ 862252-69-5 ]
  • 8
  • [ 3144-09-0 ]
  • [ 1122-91-4 ]
  • [ 83922-54-7 ]
YieldReaction ConditionsOperation in experiment
58% With potassium phosphate; copper(l) iodide; dimethylaminoacetic acid; In N,N-dimethyl-formamide; for 16h;Reflux; A mixture of 4-bromobenzaldehyde (0.250 g, 1.40 mmol), methanesulfonamide (0.154 g, 1.62 mmol), copper iodide (0.0510 g, 0.270 mmol), N,N-dimethylglycine (0.0280 g, 0.270 mmol), and potassium phosphate tribasic (0.716 g, 3.38 mmol) in DMF (5.00 mL) was stirred at reflux for 16 hours. The mixture was diluted with EtOAc (50 mL), washed with water (50 mL), and then saturated aqueous LiCl (5 mL). The combined aqueous layers were then back-extracted with EtOAc (50 mL). The organic layers were combined, washed with brine (50 mL), dried over Na2SO4, filtered, and the solvent was removed under reduced pressure, to provide N-(4-formylphenyl)methanesulfonamide (0.161 g, 58%) as a yellow oil
58% With potassium phosphate; copper(l) iodide; dimethylaminoacetic acid; In N,N-dimethyl-formamide; for 16h;Reflux; Example 60 Preparation of N-(4-(5,7-Dimethoxy-4-oxo-3,4-dihydroquinazolin-2-yl)phenyl)methanesulfonamide A mixture of 4-bromobenzaldehyde (0.250 g, 1.40 mmol), methanesulfonamide (0.154 g, 1.62 mmol), copper iodide (0.0510 g, 0.270 mmol), N,N-dimethylglycine (0.0280 g, 0.270 mmol), and potassium phosphate tribasic (0.716 g, 3.38 mmol) in DMF (5.00 mL) was stirred at reflux for 16 hours. The mixture was diluted with EtOAc (50 mL), washed with water (50 mL), and then saturated aqueous LiCl (5 mL). The combined aqueous layers were then back-extracted with EtOAc (50 mL). The organic layers were combined, washed with brine (50 mL), dried over Na2SO4, filtered, and the solvent was removed under reduced pressure, to provide N-(4-formylphenyl)methanesulfonamide (0.161 g, 58%) as a yellow oil.
  • 9
  • [ 75-52-5 ]
  • [ 83922-54-7 ]
  • <i>N</i>-[4-(1-hydroxy-2-nitro-ethyl)-phenyl]-methanesulfonamide [ No CAS ]
  • 10
  • [ 83922-54-7 ]
  • <i>N</i>-[4-(2-amino-1-triethylsilanyloxy-ethyl)-phenyl]-methanesulfonamide [ No CAS ]
  • 11
  • [ 83922-54-7 ]
  • <i>N</i>-[4-(2-nitro-1-triethylsilanyloxy-ethyl)-phenyl]-methanesulfonamide [ No CAS ]
  • 12
  • [ 83922-54-7 ]
  • (+/-)-N-(4-{1-hydroxy-2-[3-(6-imidazol-1-yl-4-methyl-1H-benzimidazol-2-yl)-2-oxo-1,2-dihydro-pyridin-4-ylamino]-ethyl}-phenyl)-methanesulfonamide [ No CAS ]
  • 13
  • [ 83922-54-7 ]
  • [ 64261-93-4 ]
  • 14
  • [ 19073-14-4 ]
  • [ 83922-54-7 ]
  • 15
  • [ 2403-53-4 ]
  • [ 83922-54-7 ]
  • 16
  • [ 555-16-8 ]
  • [ 83922-54-7 ]
  • 17
  • [ 83922-54-7 ]
  • <i>N</i>-{4-[3-(4-chloro-phenyl)-4-hydroxy-5-oxo-2,5-dihydro-furan-2-yl]-phenyl}-methanesulfonamide [ No CAS ]
  • 18
  • [ 83922-54-7 ]
  • <i>N</i>-{4-[3-(ethyl-heptyl-amino)-1-hydroxy-2-methyl-propyl]-phenyl}-methanesulfonamide [ No CAS ]
  • 19
  • [ 83922-54-7 ]
  • [ 862252-70-8 ]
  • 20
  • [ 83922-54-7 ]
  • [ 100632-81-3 ]
  • 21
  • [ 83922-54-7 ]
  • [ 42747-84-2 ]
  • C14H17N5O4S [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% In ethanol; for 3h;Heating / reflux; A mixture of [INTERMEDIATE] 11 (0.0088 mol) [AND N- (4-FONNYLPHENYL)-] [METHANESULFONAMIDE] (0.012 mol) in [ETOH] (20ml) was stirred and refluxed for 3 hours, then brought to room temperature. The precipitate was filtered off and dried. Yielding: 2.34g of intermediate 30 (75%).
  • 22
  • [ 774238-85-6 ]
  • [ 83922-54-7 ]
YieldReaction ConditionsOperation in experiment
90% With manganese(IV) oxide; In tetrahydrofuran; at 60℃; for 8h;Inert atmosphere; [0264] Step G: To a solution of compound 5-6 (230 mg, 1.1 mmol) and in 10 mL of THF was add slowly Mn02 (200 mg, 2.2 mmol). The mixture was stirred at 60 C under N2 for 8h. The mixture was filtered and the organic solvent was concentrated. Compound 5-7 was obtained after silica gel column chromatography (eluent: PE/EA = 5 : 1) as a brown solid (200 mg, yield: 90%).
65% With manganese(IV) oxide; In tetrahydrofuran; at 50℃; N-[4-(HYDROXYMETHYL) PHENYL] METHANESULFONAMIDE (0. 99 G, 4. 91 MMOL) was dissolved in THF (15 mL) and treated with MNO2 (1. 01 G, 9. 83 MMOL). The reaction was stirred at 50 C overnight. The Manganese oxide was then filtered through celite and the filtrate was purified with 40 S Biotage eluting with 40-50% EtOAc in hexanes to obtain N- (4- formylphenyl) methanesulfonamide as a white solid (0. 64 g, 65 %) :'H NMR (DMSO-d6) 8 10. 47 (s, 1H), 9. 86 (s, 1H), 7. 86 (d, 2H), 7. 33 (d, 2H), 3. 13 (s, 3H).
  • 23
  • (3R)-1-butyl-2,5-dioxo-3-((1R)-1-hydroxy-1-cyclohexylmethyl)-1,4,9-triazaspiro[5.5]undecane hydrochloride [ No CAS ]
  • [ 83922-54-7 ]
  • (3R)-1-butyl-2,5-dioxo-3-((1R)-1-hydroxy-1-cyclohexylmethyl)-9-(4-methylsulfonylaminophenylmethyl)-1,4,9-triazaspiro[5.5]undecane hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
To a solution of the compound prepared in Reference Example 2 (100 mg) in dimethyl formamide (3 mL) was added acetic acid (16 muL) (or triethylamine (40 muL)). To the reaction mixture was added <strong>[83922-54-7]N-(4-formylphenyl)methanesulfonamide</strong> (56 mg) and sodium triacetoxyborohydride (82 mg). The reaction mixture was stirred at room temperature overnight. The reaction mixture was concentrated, the obtained residue was purified by column chromatography on silica gel (ethyl acetate : methanol = 20 : 1-10 : 1) and 4N hydrogen chloride / ethyl acetate solution was added thereto. The reaction mixture was concentrated to give the compound of the present invention (72 mg) having the following physical data. TLC: Rf 0.67 (dichloromethane:methanol=5:1); NMR(CD3OD): delta 7.53, 7.34, 4.32, 4.15, 3.99, 3.74, 3.54-3.42, 3.33-3.16, 3.01, 2.49-2.24, 2.14- 1.91, 1.80-1.60, 1.40-1.15, 1.00-0.87.
  • 24
  • [ 19073-14-4 ]
  • [ 124-63-0 ]
  • [ 83922-54-7 ]
YieldReaction ConditionsOperation in experiment
42% A solution of 4-nitrobenzaldehyde (6.60 g, 43.67 mmol) andp-toluenesulfonic acid monohydrate (153 mg, 0.804 mmol) were dissolved in 150 mL of toluene. Ethylene glycol (5 mL) was added, and the solution was refluxed with a Dean-Stark trap to azeotropically remove water. After 1 hour, the reaction was allowed to cool, whereupon 100 mL of diethyl ether was added. The solution was washed with twice with saturated NaHC03 solution and then with saturated NaCI solution. The solution was dried over MgS04 and evaporated to yield 4-nitrobenzaldehyde ethylene glycol acetal as a yellow solid (8.13 g, 95% yield). Pt02 (502 mg, 2.21 mmol) and MgS04 (7.34 g, 61.0 mmol) were added to a solution of 4-nitrobenzaldehyde ethylene glycol acetal (5.93 g, 30.4 mmol) in 60 mL of THF. The resulting suspension was stirred under 70 psi H2 for 5 h. Solids were removed by filtration, and the filtrate was evaporated to give 4-aminobenzaldehyde ethylene glycol acetal as a golden liquid. 4-Aminobenzaldehyde ethylene glycol acetal (1.793 g, 10.86 mmol) was dissolved in 25 mL CH2Cl2 and cooled to 0 C. Pyridine was added (925 mg, 11.7 mmol), followed by dropwise addition of methanesulfonyl chloride (1.369 g, 11.9 mmol) over 30 min. The solution was allowed to warm to room temperature with stirring. After 16 h, 6 MNaOH (5 mL) was added followed by 150 mL of water. The aqueous layer was separated, washed with 50 mL CH2Cl2 and then acidified to pH 1 with 2 M HCI. The resulting suspension was extracted into ethyl acetate (4 x 50 mL) which was dried over MgS04 and evaporated to give 4-methanesulfonyl benzaldehyde as an orange solid (920 mg, 42% yield.
  • 26
  • [ 75-52-5 ]
  • [ 83922-54-7 ]
  • [ 1233215-20-7 ]
  • 27
  • [ 2033-24-1 ]
  • [ 83922-54-7 ]
  • [ 1370290-36-0 ]
  • 28
  • [ 83922-54-7 ]
  • [ 1370290-54-2 ]
  • 29
  • [ 83922-54-7 ]
  • [ 1391622-94-8 ]
  • 30
  • [ 91918-90-0 ]
  • [ 83922-54-7 ]
  • [ 1392812-68-8 ]
  • 31
  • [ 63920-73-0 ]
  • [ 83922-54-7 ]
  • [ 1246250-24-7 ]
YieldReaction ConditionsOperation in experiment
11% With toluene-4-sulfonic acid; sodium hydrogensulfite; In N,N-dimethyl acetamide; at 155℃; for 16h; A mixture of <strong>[83922-54-7]N-(4-formylphenyl)methanesulfonamide</strong> (0.161 g, 0.0800 mmol), 2-amino-4,6-dimethoxybenzamide (0.159 g, 0.0800 mmol), NaHSO3 (94%, 0.00460 g, 0.0240 mmol), and p-TsOH.H2O (0.0125 g, 0.120 mmol) in DMA (1.00 mL) was heated at 155 C. for 16 hours. The mixture was diluted with EtOAc (50 mL), washed with water (2*50 mL), then brine (50 mL), dried over Na2SO4, filtered, and the solvent was removed under vacuum. The residue was purified over silica gel (12 g, CH2Cl2/MeOH) and the product was freeze-dried from MeCN/H2O to provide the title compound (0.0341 g, 11%) as a pale yellow solid. 1H NMR (300 MHz, DMSO-d6): delta 11.94 (s, 1H), 10.21 (s, 1H), 8.16 (d, J=8.76 Hz, 2H), 7.30 (d, J=8.76 Hz, 2H), 6.72 (d, J=2.25 Hz, 1H), 6.52 (d, J=2.25 Hz, 1H), 3.89 (s, 3H), 3.85 (s, 3H), 3.09 (s, 3H). MS (ESI) m/z 376 [C17H17N3O6S+H]+
11% With toluene-4-sulfonic acid; sodium hydrogensulfite; In N,N-dimethyl acetamide; at 155℃; for 16h; A mixture of <strong>[83922-54-7]N-(4-formylphenyl)methanesulfonamide</strong> (0.161 g, 0.0800 mmol), 2-amino-4,6-dimethoxybenzamide (0.159 g, 0.0800 mmol), NaHSO3 (94%, 0.00460 g, 0.0240 mmol), and p-TsOH.H2O (0.0125 g, 0.120 mmol) in DMA (1.00 mL) was heated at 155 C. for 16 hours. The mixture was diluted with EtOAc (50 mL), washed with water (2*50 mL), then brine (50 mL), dried over Na2SO4, filtered, and the solvent was removed under vacuum. The residue was purified over silica gel (12 g, CH2Cl2/MeOH) and the product was freeze-dried from MeCN/H2O to provide the title compound (0.0341 g, 11%) as a pale yellow solid. 1H NMR (300 MHz, DMSO-d6): delta 11.94 (s, 1H), 10.21 (s, 1H), 8.16 (d, J=8.76 Hz, 2H), 7.30 (d, J=8.76 Hz, 2H), 6.72 (d, J=2.25 Hz, 1H), 6.52 (d, J=2.25 Hz, 1H), 3.89 (s, 3H), 3.85 (s, 3H), 3.09 (s, 3H). MS (ESI) m/z 376 [C17H17N3O5S+H]+.
  • 32
  • [ 171277-86-4 ]
  • [ 83922-54-7 ]
  • N<SUP>1</SUP>-(4-(N-(4-formylphenyl)methanesulfonamide)benzylidene)-N<SUP>4</SUP>-(2,6-dimethylphenyl)semicarbazone [ No CAS ]
  • 33
  • [ 491-37-2 ]
  • [ 105-56-6 ]
  • [ 83922-54-7 ]
  • (N-4-(3-cyano-2-oxo-2,5-dihydro-1H-chromeno[4,3-b]pyridin-4-yl)phenyl)methanesulfonamide [ No CAS ]
  • 34
  • [ 109-83-1 ]
  • [ 83922-54-7 ]
  • C11H18N2O3S [ No CAS ]
  • 35
  • [ 83922-54-7 ]
  • diethyl (fluoro(4-(methylsulfonamido)phenyl)methyl)phosphonate [ No CAS ]
  • 36
  • [ 83922-54-7 ]
  • (Z)-N-(4-(2-(3-(tert-butyl)-5-(2,4-dioxotetrahydropyrimidin-1(2H)-yl)-6-fluoro-2-methoxyphenyl)-1-fluorovinyl)phenyl)methanesulfonamide [ No CAS ]
  • 37
  • [ 598-02-7 ]
  • [ 83922-54-7 ]
  • diethyl (hydroxy(4-(methylsulfonamido)phenyl)methyl)phosphonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% With sodium methylate; In methanol; at 20℃; for 12h; Step 1) diethyl (hydroxy (4- (methylsulfonamido) phenyl) methyl) phosphonate To a mixture of N- (4-formylphenyl) methanesulfonamide (2 g, 10 mmol) and diethyl phosphate (1.4 g, 10 mmol) was added a solution of sodium methoxide in methanol (0.5 mL, 0.25 mmol) . The mixture was stirred at rt for 12 hours. The reaction mixture was diluted with dichloromethane (20 mL) and washed with saturated aqueous NH4Cl (10 mL) , and dried over anhydrous Na2SO4and concentrated in vacuo. The residue was purified by silica gel column chromatography eluted with PE : EtOAc (V : V) 10 : 1 to give diethyl (hydroxy (4- (methylsulfonamido) phenyl) methyl) phosphonate as gray oil (2.9 g, 87) .[1120]MS (ESI, pos. ion) m/z: 338.3 [M+H]+.
  • 38
  • 2,2,2-trifluoro-N-(trans-2-phenylcyclopropyl)-N-(piperidin-4-ylmethyl)acetamide [ No CAS ]
  • [ 83922-54-7 ]
  • 2,2,2-trifluoro-N-((1-(4-(methylsulfonamido)benzyl)piperidin-4-yl)methyl)-N-((trans)-2-phenylcyclopropyl)acetamide, hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
210 mg With sodium tris(acetoxy)borohydride; In 1,2-dichloro-ethane; at 20℃; for 32h; Added sodium triacetoxyborohydride (180 mg, 0.850 mmol) to a solution of 2,2,2-trifluoro-N-((trans)-2-phenylcyclopropyl)-N-(piperidin-4-ylmethyl)acetamide (185 mg, 0.567 mmol), <strong>[83922-54-7]N-(4-formylphenyl)methanesulfonamide</strong> (124 mg, 0.624 mmol) in 1,2-Dichloroethane (DCE) (40 mL). Let stir at RT for 16 hours. Added 100 mg of sodium triacetoxyborohydride and let stir at RT for 16 hours. Concentrated on a rotovap. Added water and extracted with DCM. Combined DCM extracts and washed with brine, dried over MgSO4, filtered and rotovapped off DCM. The residue was purified via Biotage (0% to 100% EtOAc:Hex then 0% to 20% MeOH:DCM 25 g-HP-silica gel column). Obtained 210 mg. 1H NMR (400 MHz, CHLOROFORM-d) delta ppm 1.47 (br. s., H), 1.90 (br. s., 4H), 2.08-2.27 (m, 3H), 2.39 (br. s., 1H), 2.65 (s, 1H), 3.04 (br. s., 4H), 3.23-3.76 (m, 3H), 4.14 (br. s., 2H), 6.99-7.15 (m, 2H), 7.2-7.3 (m 3H), 7.46 (br. s., 23H), 7.63 (br. s., 2H), 9.05 (br. s., 1H), 11.69 (br. s., 1H)
  • 39
  • 2,2,2-trifluoro-N-(trans-2-phenylcyclopropyl)-N-(piperidin-4-ylmethyl)acetamide [ No CAS ]
  • [ 83922-54-7 ]
  • N-(4-((4-((((trans)-2-phenylcyclopropyl)amino)methyl)piperidin-1-yl)methyl)phenyl)methanesulfonamide dihydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
10.1 mg Added 1M sodium hydroxide (1 mL, 1 .000 mmol) to a solution of 2,2,2-tritluoro-N-((1-(4-(methylsulfonamido)benzyl)piperidin-4-yl)methyl)-N-((trans)-2-phenylcyclopropyl)acetamide (170 mg. 0.334 mmol) in methanol (3 ml,) and let stir at RT for 16 hours. Concentrated and HPLC purification (reverse phase) was performed on an open-access Gilson using Trilutionsoftware, with a Gemini NI 5u C18 110A, AXIA. 100x30.00 mm 5 micron. An 7 minute gradient run (0% AcCN/H2O 0.1% Formic Acid to 40% ACNIII,O, 0.1%Fomic Acid) with UVdetection at 214 nm was utilized. Added 1 ml of 1N HCl to fractions containing product and evaporated. Obtained 10,1 mg
  • 40
  • 2,2,2-trifluoro-N-(trans-2-phenylcyclopropyl)-N-(piperidin-4-ylmethyl)acetamide [ No CAS ]
  • [ 83922-54-7 ]
  • 2,2,2-trifluoro-N-((1-(4-(methylsulfonamido)benzyl)piperidin-4-yl)methyl)-N-((trans)-2-phenylcyclopropyl)acetamide hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
210 mg With sodium tris(acetoxy)borohydride; In 1,2-dichloro-ethane; at 20℃; for 32h; Added sodium triacetoxyborohydride (180 mg, 0.850 mmol) to a solution of 2,2,2-trifluoro-N-((trans)-2- phenylcyclopropyl)-N-(piperidin-4-ylmethyl)acetamide(185 mg, 0,567 mmol), <strong>[83922-54-7]N-(4-formylphenyl)methanesulfonamide</strong> (124 mg, 0.624 mmol) in 1,2-Dichloroethane(DCE) (40 mL). Let stir at RT for 16 hours Added 100 mg of sodium triacetoxyborohydride and let stir at RT for 16 hours. Concentrated on a rotovap. Added water and extracted with DCM. Combined DCM extracts and washed with brine, dried over MgSO4. filtered and rotovapped off DCM. The residue was purified via Biotage (0% to 100% EtOAc:Hex then 0%to 20% MeOH:DCM 25 g-HP silica gel column). Obtained 210 mg
  • 41
  • [ 914250-39-8 ]
  • [ 83922-54-7 ]
  • N-(4-((2-([1,3]dioxolo[4,5-g]quinolin-8-yl)hydrazono)methyl)phenyl)methanesulfonamide [ No CAS ]
  • 42
  • [ 65197-42-4 ]
  • [ 83922-54-7 ]
  • N-(4-((2-(1,2,3,4-tetrahydroacridin-9-yl)hydrazono)methyl)phenyl)methanesulfonamide [ No CAS ]
  • 43
  • [ 49612-12-6 ]
  • [ 83922-54-7 ]
  • N-(4-((2-(6-methoxy-2-methylquinolin-4-yl)hydrazono)methyl)phenyl)methanesulfonamide [ No CAS ]
  • 44
  • [ 49612-20-6 ]
  • [ 83922-54-7 ]
  • N-(4-((2-(7-methoxy-2-methylquinolin-4-yl)hydrazono)methyl)phenyl)methanesulfonamide [ No CAS ]
  • 45
  • [ 49612-23-9 ]
  • [ 83922-54-7 ]
  • N-(4-((2-(7-methoxyquinolin-4-yl)hydrazono)methyl)phenyl)methanesulfonamide [ No CAS ]
  • 46
  • [ 15793-93-8 ]
  • [ 83922-54-7 ]
  • N-(4-((2-(quinolin-4-yl)hydrazono)methyl)phenyl)methanesulfonamide [ No CAS ]
  • 47
  • C38H52N7O9Pol [ No CAS ]
  • [ 83922-54-7 ]
  • C46H59N8O11PolS [ No CAS ]
  • 48
  • [ 5192-03-0 ]
  • [ 108-94-1 ]
  • [ 83922-54-7 ]
  • N-(4-(8,9,10,11-tetrahydro-3H-pyrrolo[3,2-a]phenanthridin-7-yl)phenyl)methanesulfonamide [ No CAS ]
  • 49
  • [ 109-97-7 ]
  • [ 83922-54-7 ]
  • 5,10,15,20-mesotetrakis(4-methylsulfonamidophenyl)-21H,23H-porphyrine [ No CAS ]
  • 50
  • [ 619-45-4 ]
  • [ 83922-54-7 ]
  • 51
  • [ 50790-28-8 ]
  • [ 83922-54-7 ]
  • 52
  • C16H20F3N5S [ No CAS ]
  • [ 83922-54-7 ]
  • C24H29F3N6O2S2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
36% [0274] A solution of compound 5-7 (40 mg, 0.2 mmol), compound 6-2 (75 mg, 0.2 mmol) and TEA (120 mg, 1.2 mmol) in 15 mL of DCM was stirred at room temperature for 2 hours before NaBH(OAc)3 (255 mg, 1.2 mmol) was added. The reaction mixture was stirred at room temperature overnight. The reaction mixture was partitioned between DCM and NaHC03 (sat.), and the organic layer was washed by brine and dried over Na2S04. Solvent was removed under vacuum to get a residue, which was purified by Prep-TLC(DCM/MeOH=15: 1) to give 26 as a solid (40 mg, yield: 36%). ESI-MS m/z: 555.18 (M+H). 1HNMR (400MHz, DMSO): 9.72 (br, 1H), 7.16-7.40 (m, 5H), 4.86 (d, J = 4.8 Hz, 1H), 3.86 (q, J= 10.8 Hz, 2H), 3.14-3.72 (m, 8H), 2.98 (s, 3H), 2.78 (d, J= 4.4 Hz, 3H), 2.50-2.70 (m, 2H), 1.68-2.00 (m, 4H).
  • 53
  • 2-methyl-4-(2,7-diazaspiro[4.4]nonan-2-yl)-6-(2,2,2-trifluoroethyl)thieno[2,3-d]pyrimidine [ No CAS ]
  • [ 83922-54-7 ]
  • C24H28F3N5O2S2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
40% [0265] Step H: A solution of compound 5-7 (60 mg, 0.27 mmol), compound 1-6 (90 mg, 0.25 mmol) and TEA (150 mg, 1.5 mmol) in 15 mL of DCM was stirred at room temperature for 2 hours before NaBH(OAc)3 (320 mg, 1.5 mmol) was added. The mixture reaction was stirred at room temperature overnight. The reaction was partitioned between DCM and NaHC03 (sat.), and the organic layer was washed by brine and dried over Na2S04. The solvent was removed under vacuum and the residue was purified by Prep-TLC (DCM/MeOH = 20: 1) to give compound 25 as a solid (60 mg, yield: 40%). ESI-MS m/z: 540 12 (M+H). 1HNMR (400MHz, DMSO): 9.66 (s, 1H), 7.63(s, 1H), 7.19-7.30 (dd, 4H, J= 8.8 Hz), 4.04 (q, J= 10.4 Hz, 2H), 3.50-3.95 (m, 6H), 2.96 (s, 3H), 2.40-2.65 (m, 4H), 2.42 (s, 3H), 1.78-2.05 (m, 4H).
  • 54
  • C26H34N6O3 [ No CAS ]
  • [ 83922-54-7 ]
  • C34H43N7O5S [ No CAS ]
YieldReaction ConditionsOperation in experiment
28.2 mg General procedure: Toa solution of 3-(methylsulfonamido)benzaldehyde (31.9mg, 0.16 mmol) and acetic acid (0.018 mL) in methanol (0.4 mL) was added asolution of compound 11a (38.3 mg,0.08 mmol) in tetrahydrofuran (0.2 mL), followed by stirring at roomtemperature under a nitrogen atmosphere. After 15 min, sodium cyanoborohydride(1.0 M in tetrahydrofuran, 0.16 mL, 0.16 mmol) was added to the reactionmixture and the resulting mixture was stirred at room temperature for 1 hour.The mixture was directly subjected to flash column chromatography on silica gel(50:50 to 33:67 hexane/ethyl acetate) to give 26.2 mg of compound 12a.
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