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[ CAS No. 873663-50-4 ] {[proInfo.proName]}

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Chemical Structure| 873663-50-4
Chemical Structure| 873663-50-4
Structure of 873663-50-4 * Storage: {[proInfo.prStorage]}
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Product Details of [ 873663-50-4 ]

CAS No. :873663-50-4 MDL No. :MFCD22494032
Formula : C12H19BN2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :YIPXXWWEXMOZPZ-UHFFFAOYSA-N
M.W : 234.10 Pubchem ID :66617788
Synonyms :

Calculated chemistry of [ 873663-50-4 ]

Physicochemical Properties

Num. heavy atoms : 17
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.5
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 2.0
Molar Refractivity : 71.73
TPSA : 70.5 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.63 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 1.55
Log Po/w (WLOGP) : 1.17
Log Po/w (MLOGP) : 0.55
Log Po/w (SILICOS-IT) : 0.39
Consensus Log Po/w : 0.73

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.46
Solubility : 0.806 mg/ml ; 0.00344 mol/l
Class : Soluble
Log S (Ali) : -2.64
Solubility : 0.536 mg/ml ; 0.00229 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.29
Solubility : 0.121 mg/ml ; 0.000518 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.96

Safety of [ 873663-50-4 ]

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 [ 873663-50-4 ]

* 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 [ 873663-50-4 ]

[ 873663-50-4 ] Synthesis Path-Downstream   1~36

  • 1
  • [ 1421322-66-8 ]
  • [ 873663-50-4 ]
YieldReaction ConditionsOperation in experiment
With hydrogen; In acetic acid; at 40℃; for 1.0h; A solution of (3-acetamido-2-nitrophenyl)boronic acid (300 mg) in 2M aqueous hydrochloric acid solution (4 mL) was heated at 80 C. for 20 min. After cooling to room temperature, the solvent was reduced in vacuo to give a brown solid which was redissolved in 1,4-dioxane (5 mL). Pinacol (316 mg) was added and the mixture heated at 100 C. for 30 min. After cooling to room temperature the solvent was reduced in vacuo to give a beige solid which was dissolved in acetic acid (5 mL). Palladium on carbon (100 mg) was added and the mixture stirred under an atmosphere of hydrogen at 40 C. for 1 h. The reaction mixture was then filtered through Celite and the filtrate reduced in vacuo. Purification by column chromatography gave 2-amino-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline.
  • 2
  • [ 873566-64-4 ]
  • [ 873663-50-4 ]
  • 2-(2,3-diaminophenyl)-4-{3-[N-(tert-butoxycarbonylpiperidin-3-yl)carbonylamino]phenyl}-6-morpholinopyrimidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water; at 140℃; for 0.166667h;microwave radiation; A mixture 4-{3-[A^-(fer?-butoxycarbonyl)piperidin-3-ylcarbonylamino]phenyl}-2-chloro-6-morpholinopyrimidine (0.15 g), 3-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)benzene-l,2-diamine (0.072 g), tetrakis(triphenylphosphme)palladium(0) (6 mg), asaturated aqueous solution of sodium carbonate (0.127 g) and 1,4-dioxane (18 ml) was placedin a sealed glass tube under an atmosphere of nitrogen and heated to 140C using microwaveradiation for 10 minutes. The reaction mixture was allowed to cool to ambient temperature.The mixture was evaporated and the residue was suspended in a 10:1 mixture of methylenechloride and methanol. The supernatant solution was decanted from inorganic material andevaporated. The resultant residue was purified by column chromatography on silica using anincreasingly polar gradient of 0% to 5% methanol in methylene chloride as eluent. There wasthus obtained 2-(2,3-diaminophenyl)-4-{3-[A^-(te7t-butoxycarbonyl)piperidin-3-ylcarbonylamino]phenyl}-6-morpholinopyrimidine as a gum (0.171 g); Mass Spectrum:M+H^ 574.
  • 3
  • [ 873663-49-1 ]
  • [ 873663-50-4 ]
YieldReaction ConditionsOperation in experiment
With hydrogen; acetic acid;palladium 10% on activated carbon; at 40℃; under 760.051 Torr; for 1.0h; A solution of a portion (1.4 g) of the material so obtained, 10% palladium on charcoalcatalyst (0.5 g) and glacial acetic acid (10 ml) was stirred under an atmosphere pressure ofhydrogen and heated to 40C for 1 hour. The reaction mixture was filtered and the filtrate wasevaporated. The residue was purified by column chromatography on silica using anincreasingly polar gradient of 0% to 10% methanol in methylene chloride as eluent. There wasthus obtained 3-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)benzene-l,2-diamine as a solid(0.42 g); NMR Spectrum: 1.31 (s, 12H), 6.37 (t, 1H), 6.63 (d, 1H), 6.79 (d, 1H).
With palladium on activated charcoal; hydrogen; In methanol; dichloromethane; at 20℃; under 1140.08 Torr; for 16.0h; Step B: 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene-1,2-diamine (1212) Into a 250-mL round-bottom flask, was placed a solution of 2-nitro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (5.00 g, 18.93 mmol) in DCM (20 mL) and MeOH (20 mL). This was followed by the additional of Pd/C (20.15 g, 18.93 mmol) at ambient temperature. The resulting mixture was degassed with nitrogen for 3 times, and then bubbled with hydrogen for 3 times. After the resulting mixture was stirred under hydrogen for 16 hr at ambient temperature at 1.5 atm, it was filtered and the filter cake was washed with DCM (3×10 mL). The combined organic layers were concentrated in vacuo and purified by silica gel column chromatography, eluted with EtOAc/PE (2/3) to afford the title compound: LCMS (ESI) calc'd for C12H19BN2O2 [M+H]+: 235. found 235.
With palladium on activated charcoal; hydrogen; In methanol; dichloromethane; at 20℃; under 1140.08 Torr; for 16.0h; Into a 250-mL round-bottom flask, was placed a solution of 2-nitro-3-(4,4,5,5- tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (5.00 g, 18.93 mmol) in DCM (20 mL) and MeOH (20 mL). This was followed by the addition of Pd/C (20.15 g, 18.93 mmol) at ambient temperature. The reaction mixture was degassed with nitrogen for 3 times, and then with hydrogen for 3 times. The mixture was stirred under hydrogen for 16 hrat ambient temperatureat1.5 atm. The mixture was filtered and the filter cake was washed with DCM (3 x 10 mL). The combined organic layers were concentrated under reduced pressure and purified by silica gel column chromatography, eluting with EA/PE (2/3) to affordthe title compound as a solid:LCMS (ESI) calc?d for C,2H,9BN202[M + H]: 235, found 235; ?H NMR (400 MHz, CDC13): oe 7.21 (d, J= 7.6 Hz, 1H), 6.79 (d, J= 7.6 Hz, 1H) , 6.65 (t, J= 7.6 Hz, 1H), 3.60 (br, 4H), 1.34 (s, 12H).
  • 4
  • [ 873663-50-4 ]
  • [ 1198436-89-3 ]
  • [ 1198803-97-2 ]
YieldReaction ConditionsOperation in experiment
With sodium carbonate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,4-dioxane; water; at 150℃; for 0.25h;Microwave irradiation; Example 82lambda/-[6-(1 H-Benzimidazol-4-yl)-1 H-indazol-4-yl]-2-methyl-1 ,3-thiazole-4-carboxamide lambda/-(6-Bromo-1 H-indazol-4-yl)-2-methyl-1 ,3-thiazole-4-carboxamide (200mg), 3-(4,4,5,5- tetramethyl-1 ,3,2-dioxaborolan-2-yl)-1 ,2-benzenediamine (167mg) (WO2006/005915, page 90-91 ), Pd(dppf)CI2 (43mg) and 2M sodium carbonate (0.890ml) were charged in 1 ,4-dioxane (2ml) and water (2ml). The reaction vial was sealed and heated under microwave irradiation at 1500C for 15min. The reaction was extracted with DCM (3x30ml). The combined organic layers were evaporated. To a solution of the residue in DMF (3ml) was added triethylorthoformate (10ml) and the mixture heated at reflux for 2h. The solvent was evaporated and the residue dissolved in methanokDMSO (3ml, 1 :1 ) and purified by mass directed preparative HPLC (Method A) to give title compound (26mg). LC/MS R1 0.78min m/z 375 [MH+]. Method B
With sodium carbonate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,4-dioxane; water; at 150℃; for 0.25h;Microwave irradiation; Example 114 lambda/-[6-(2,3-Diaminophenyl)-1H-indazol-4-yl]-2-methyl-1 ,3-thiazole-4-carboxamide <n="188"/>N-(6-Bromo-1 H-indazol-4-yl)-2-methyl-1 ,3-thiazole-4-carboxamide (200 mg,), 3-(4,4,5,5- tetramethyl-1 ,3,2-dioxaborolan-2-yl)-1 ,2-benzenediamine (167 mg) (which may be prepared as described in WO2006005915), Pd(dppf)CI2 (43 mg) and sodium carbonate (890 mul) were added to a microwave vial followed by 1 ,4-dioxane (2 ml) and water (2 ml). The mixture was heated under microwave irradiation at 1500C for 15 min. The reaction was diluted with DCM (30 ml) and the layers separated. The aqueous layer was extracted further with DCM (2 x 30 ml) and the combined organic extracts were evaporated to dryness to give the title compound (250 mg). LCMS (Method B) Rt = 0.81 min, MH+ = 365.
  • 5
  • [ 73183-34-3 ]
  • [ 873663-50-4 ]
  • 6
  • [ 873663-50-4 ]
  • 6-bromo-3-iodo-N,N-bis[(4-methoxyphenyl)methyl]-2-[2-[(4-methoxyphenyl)methyl]-2H-1,2,3,4-tetrazol-5-yl]benzene-1-sulfonamide [ No CAS ]
  • 2’,3‘-diamino-4-bromo-N,N-bis(4-methoxybenzyl)-2-(2-(4-methoxybenzyl)-2H-tetrazol-5-yl)-[1,1‘-biphenyl]-3-sulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,4-dioxane; water; at 80℃; for 18.0h;Inert atmosphere; Step C: 5?,6?-diamino-4-bromo-N,N-bis(4-methoxybenzyl)-2-(2-(4-methoxybenzyl)-2H-tetrazol-5-yl)biphenyl-3-sulfonamide (1213) Into a 50-mL round-bottom flask purged and maintained with an inert atmosphere of argon, was placed a solution of 6-bromo-3-iodo-N,N-bis(4-methoxybenzyl)-2-(2-(4-methoxybenzyl)-2H-tetrazol-5-yl)benzenesulfonamide (0.77 g, 0.97 mmol), <strong>[873663-50-4]3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene-1,2-diamine</strong> (0.50 g, 2.13 mmol) and Pd(Ph3P)4 (0.11 g, 0.10 mmol) in dioxane (10 mL). This was followed by the addition of Na2CO3 (0.31 g, 2.90 mmol) in water (1 mL) at ambient temperature. The resulting mixture was stirred at 80 C. for 18 hr under argon and then was cooled down to 20 C., quenched with water (50 mL) and extracted with EtOAc (3×50 mL). The combined organic phase was washed with brine (3×50 mL), dried over anhydrous Na2SO4 and concentrated under reduced pressure. The residue was purified by silica gel column chromatography, eluted with EA/PE (3/2) to afford the title compound, which was used in the next step directly. LCMS (ESI) calc'd for C37H36BrN7O5S [M+H]+: 770, 772 (1:1). found 770, 772 (1:1).
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,4-dioxane; water; at 20 - 80℃; for 18.0h;Inert atmosphere; Into a 50-mL round-bottom flask purged and maintained with an inert atmosphere of argon, was placed a solution of 6-bromo-3-iodo-N,N-bis(4-methoxybenzyl)-2-(2-(4- methoxybenzyl)-2H-tetrazol-5 -yl)benzenesulfonamide (0.77 g, 0.97 mmol), 3 -(4,4,5,5 - tetramethyl- 1,3 ,2-dioxaborolan-2-yl)benzene- 1 ,2-diamine (0.50 g, 2.13 mmol) and Pd(Ph3P)4 (0.11 g, 0.10 mmol) in dioxane (10 mL). This was followed by the addition ofsodium carbonate (0.31 g, 2.90 mmol) in water (1 mL) at ambient temperature. The resulting mixture was stirred at 80C for 18 hrunder argon. The mixture was allowed to cool to 20C, quenched with water (50 mL) and extracted with EA (3x50 mL). The combined organic phase was washed with brine(3x50 mL),dried over anhydrous sodium sulfate and filtered. The filtrate was evaporated under reduced pressure and the residue was purified by silica gel column chromatography,eluted with EA/PE (3/2) to affordthe title compound as a solid:LCMS (ESI) calc?d for C37H36BrN7O5S [M + H]: 770, 772 (1: 1), found 770, 772 (1: 1).
  • 7
  • [ 7138-15-0 ]
  • [ 873663-50-4 ]
  • 8
  • [ 873663-50-4 ]
  • 3-(2-amino-3H-benzo[d]imidazol-4-yl)-6-bromo-N,N-bis(4-methoxybenzyl)-2-(2-(4-methoxybenzyl)-2H-tetrazol-5-yl)benzenesulfonamide [ No CAS ]
  • 9
  • [ 873663-50-4 ]
  • tert-butyl 4-(4-(2-amino-3H-benzo[d]imidazol-4-yl)-2-(N,N-bis(4-methoxybenzyl)sulfamoyl)-3-(2-(4-methoxybenzyl)-2H-tetrazol-5-yl)benzyl)piperidine-1-carboxylate [ No CAS ]
  • 10
  • [ 873663-50-4 ]
  • 3-(2-amino-3H-benzo[d]imidazol-4-yl)-N,N-bis(4-methoxybenzyl)-2-(2-(4-methoxybenzyl)-2H-tetrazol-5-yl)-6-(piperidin-4-ylmethyl)benzenesulfonamide [ No CAS ]
  • 11
  • [ 873663-50-4 ]
  • 3-(2-amino-3H-benzo[d]imidazol-4-yl)-6-(piperidin-4-ylmethyl)-2-(2H-tetrazol-5-yl)benzenesulfonamide [ No CAS ]
  • 12
  • [ 873663-50-4 ]
  • 4-(4-((S)-2-aminopropylsulfonyl)-3-sulfamoyl-2-(2H-tetrazol-5-yl)phenyl)-1H-benzo[d]imidazole-2-carboxylic acid [ No CAS ]
  • 13
  • [ 873663-50-4 ]
  • (S)-ethyl 4-(3-(N,N-bis(4-methoxybenzyl)sulfamoyl)-4-((2-((tert-butoxycarbonyl)amino)propyl)sulfonyl)-2-(2-(4-methoxybenzyl)-2H-tetrazol-5-yl)phenyl)-1H-benzo[d]imidazole-2-carboxylate [ No CAS ]
  • 14
  • [ 873663-50-4 ]
  • ethyl 4-(4-((S)-2-aminopropylsulfonyl)-2-(2-(4-methoxybenzyl)-2H-tetrazol-5-yl)-3-(N-(4-methoxybenzyl)sulfamoyl)phenyl)-1H-benzo[d]imidazole-2-carboxylate [ No CAS ]
  • 15
  • [ 873663-50-4 ]
  • ethyl 4-(4-((S)-2-aminopropylsulfonyl)-3-sulfamoyl-2-(2H-tetrazol-5-yl)phenyl)-1H-benzo[d]imidazole-2-carboxylate [ No CAS ]
  • 16
  • [ 873663-50-4 ]
  • tert-butyl (2-((2’-amino-3‘-(2-(((benzyloxy)carbonyl)amino)acetamido)-3-(N,N-bis(4-methoxybenzyl)sulfamoyl)-2-(2-(4-methoxybenzyl)-2H-tetrazol-5-yl)-[1,1’-biphenyl]-4-yl)sulfonyl)ethyl)carbamate [ No CAS ]
  • 17
  • [ 873663-50-4 ]
  • tert-butyl (2-((4-(2-((((benzyloxy)carbonyl)amino)methyl)-1Hbenzo[d]imidazol-4-yl)-2-(N,N-bis(4-methoxybenzyl)sulfamoyl)-3-(2-(4-methoxybenzyl)-2H-tetrazol-5-yl)phenyl)sulfonyl)ethyl)carbamate [ No CAS ]
  • 18
  • [ 873663-50-4 ]
  • 3-(2-amino-1H-benzo[d]imidazol-4-yl)-6-(azetidin-3-ylthio)-2-(2H-tetrazol-5-yl)benzenesulfonamide [ No CAS ]
  • 19
  • [ 873663-50-4 ]
  • tert-butyl 3-(4-(2-amino-1H-benzo[d]imidazol-4-yl)-2-(N,N-bis(4-methoxybenzyl)sulfamoyl)-3-(2-(4-methoxybenzyl)-2H-tetrazol-5-yl)phenylthio)azetidine-1-carboxylate [ No CAS ]
  • 20
  • [ 873663-50-4 ]
  • 3-(2-amino-1H-benzo[d]imidazol-4-yl)-6-(azetidin-3-ylthio)-N-(4-methoxybenzyl)-2-(2-(4-methoxybenzyl)-2H-tetrazol-5-yl)benzenesulfonamide [ No CAS ]
  • 21
  • [ 873663-50-4 ]
  • tert-butyl 4-((4-(2-amino-1H-benzo[d]imidazol-7-yl)-2-(N,N-bis(4-methoxybenzyl)sulfamoyl)-3-(2-(4-methoxybenzyl)-2H-tetrazol-5-yl)phenyl)thio)piperidine-1-carboxylate [ No CAS ]
  • 22
  • [ 873663-50-4 ]
  • 3-(2-amino-3H-benzo[d]imidazol-4-yl)-N,N-bis(4-methoxybenzyl)-2-(2-(4-methoxybenzyl)-2H-tetrazol-5-yl)-6-(piperidin-4-ylthio)benzenesulfonamide [ No CAS ]
  • 23
  • [ 873663-50-4 ]
  • 4-(4-((2-aminoethyl)sulfonyl)-3-sulfamoyl-2-(2H-tetrazol-5-yl)phenyl)-1H-benzo[d]imidazole-2-carboxylic acid [ No CAS ]
  • 24
  • [ 873663-50-4 ]
  • tert-butyl (2-((2-(N,N-bis(4-methoxybenzyl)sulfamoyl)-3-(2-(4-methoxybenzyl)-2H-tetrazol-5-yl)-4-(2-(trichloromethyl)-1H-benzo[d]imidazol-4-yl)phenyl)sulfonyl)ethyl)carbamate [ No CAS ]
  • 25
  • [ 873663-50-4 ]
  • methyl 4-(3-(N,N-bis(4-methoxybenzyl)sulfamoyl)-4-((2-((tert-butoxycarbonyl)amino)ethyl)sulfonyl)-2-(2-(4-methoxybenzyl)-2H-tetrazol-5-yl)phenyl)-1Hbenzo[d]imidazole-2-carboxylate [ No CAS ]
  • 26
  • [ 873663-50-4 ]
  • methyl 4-(4-((2-aminoethyl)sulfonyl)-2-(2-(4-methoxybenzyl)-2H-tetrazol-5-yl)-3-(N-(4-methoxybenzyl)sulfamoyl)phenyl)-1H-benzo[d]imidazole-2-carboxylate [ No CAS ]
  • 27
  • [ 873663-50-4 ]
  • methyl 4-(4-((2-aminoethyl)sulfonyl)-3-sulfamoyl-2-(2H-tetrazol-5-yl)phenyl)-1H-benzo[d]imidazole-2-carboxylate [ No CAS ]
  • 28
  • [ 873663-50-4 ]
  • 4-(3,4-disulfamoyl-2-(2H-tetrazol-5-yl)phenyl)-1H-benzo[d]imidazole-2-carboxylic acid [ No CAS ]
  • 29
  • [ 873663-50-4 ]
  • N,N-bis(4-methoxybenzyl)-2-(2-(4-methoxybenzyl)-2H-tetrazol-5-yl)-3-(2-(trichloromethyl)-1H-benzo[d]imidazol-4-yl)-6-((2-(trimethylsilyl)ethyl)sulfonyl)benzenesulfonamide [ No CAS ]
  • 30
  • [ 873663-50-4 ]
  • methyl 4-(3-(N,N-bis(4-methoxybenzyl)sulfamoyl)-2-(2-(4-methoxybenzyl)-2H-tetrazol-5-yl)-4-((2-(trimethylsilyl)ethyl)sulfonyl)phenyl)-1Hbenzo[d]imidazole-2-carboxylate [ No CAS ]
  • 31
  • [ 873663-50-4 ]
  • 2-(N,N-bis(4-methoxybenzyl)sulfamoyl)-3-(2-(4-methoxybenzyl)-2H-tetrazol-5-yl)-4-(2-(methoxycarbonyl)-1H-benzo[d]imidazol-4-yl)benzenesulfinic acid [ No CAS ]
  • 32
  • [ 873663-50-4 ]
  • methyl 4-(3-(N,N-bis(4-methoxybenzyl)sulfamoyl)-2-(2-(4-methoxybenzyl)-2H-tetrazol-5-yl)-4-sulfamoylphenyl)-1H-benzo[d]imidazole-2-carboxylate [ No CAS ]
  • 33
  • [ 873663-50-4 ]
  • methyl 4-(3,4-disulfamoyl-2-(2H-tetrazol-5-yl)phenyl)-1H-benzo[d]imidazole-2-carboxylate [ No CAS ]
  • 34
  • [ 873663-50-4 ]
  • tert-butyl (2-((2-(N,N-bis(4-methoxybenzyl)sulfamoyl)-4-iodo-3-(2-(4-methoxybenzyl)-2H-tetrazol-5-yl)phenyl)sulfonyl)ethyl)carbamate [ No CAS ]
  • tert-butyl (2-((2‘,3‘-diamino-3-(N,N-bis(4-methoxybenzyl)sulfamoyl)-2-(2-(4-methoxybenzyl)-2H-tetrazol-5-yl)-[1,1‘-biphenyl]-4-yl)sulfonyl)ethyl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,4-dioxane; water; at 80℃; for 6.0h;Inert atmosphere; Into a 50 mL round bottom flask was placed 3-(4,4,5,5-tetramethyl-1,3,2- dioxaborolan-2-yl)benzene- 1 ,2-diamine (153 mg, 0.653 mmol),tert-butyl (2-((2-(N,N-bis(4- methoxybenzyl)sulfamoyl)-4-iodo-3 -(2 -(4-methoxybenzyl)-2H-tetrazol-5 - yl)phenyl)sulfonyl)ethyl)carbamate (300 mg, 0.327 mmol),Pd(PPh3)4 (75 mg, 0.065 mmol) and sodium carbonate (104 mg, 0.980 mmol) in 1,4-dioxane (1.5 ml) and water (0.375 ml). The reaction mixture was degassed with nitrogen for 3 times and stirred at 80C for 6 hr. Then the mixture was extracted with ethyl acetate(20 mL) and washed with water(20 mL). Then theorganic layer was concentrated under vacuum. The residue was applied on a silica gel column with ethyl acetate/petrol ether(1/1) to givethe title compound: LCMS (ESI) calc?d for C44H50N80952 [M + H]: 899, found 899; ?H NMR (300 MHz, d-DMSO): oe 8.65-8.63 (d, J 8.1 Hz, 1H), 8.13-8.10 (d, J= 8.4 Hz, 1H), 7.23-7.06 (m, 1H), 7.06-6.89 (m, 6H), 6.89-6.71 (m, 6H), 6.55-6.39 (d, J= 7.2 Hz, 1H), 6.3 1-6.12 (t, J= 7.5 Hz, 1H), 5.96-5.80 (d, J= 7.5 Hz, 1H), 5.02 (s, 2H), 4.80-4.39 (m, 4H),4.10-3.92 (m, 2H), 3.71 (s, 9H), 3.53-3.38 (m, 2H), 1.35(s, 9H).
  • 35
  • [ 873663-50-4 ]
  • (S)-tert-butyl (1-((2-(N,N-bis(4-methoxybenzyl)sulfamoyl)-4-iodo-3-(2-(4-methoxybenzyl)-2H-tetrazol-5-yl)phenyl)sulfonyl)propan-2-yl)carbamate [ No CAS ]
  • (S)-tert-butyl (1-((2’,3‘-diamino-3-(N,N-bis(4-methoxybenzyl)sulfamoyl)-2-(2-(4-methoxybenzyl)-2H-tetrazol-5-yl)-[1,1‘-biphenyl]-4-yl)sulfonyl)propan-2-yl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,4-dioxane; water; at 80℃; for 16.0h;Inert atmosphere; Into a 25 mL round bottom flask was placed (5)-tert-butyl (1-((2-(N,N-bis(4- methoxybenzyl)sulfamoyl)-4-iodo-3 -(2 -(4-methoxybenzyl)-2H-tetrazol-5 - yl)phenyl)sulfonyl)propan-2-yl)carbamate (400 mg, 0.429 mmol), 3 -(4,4,5,5 -tetramethyl- 1,3,2- dioxaborolan-2-yl)benzene-1,2-diamine (201 mg, 0.858 mmol), Pd(PPh3)4 (99 mg, 0.086 mmol) and Na2CO3 (136 mg, 1.286 mmol) in 1,4-dioxane (1.2 ml) and water (0.40 ml). Theresulting mixture was evacuated and backfilled with nitrogen 3 timesand stirred at 80C for l6hr. Thenthe mixture was diluted with EA(200 mL) and washed with water(3 x 50 mL). The organic layer was collected and washed with sat. NaC1(3 x 50 mL) and dried over anhydrous Na2SO4. Then the mixture was filtrated with the filtrate collected and concentrated under vacuum. The residue was applied on a silica gel column with EA/PE(1/1) to give the title compound as a solid: LCMS (ESI) calc?d for C45H52N809S2 [M + H]: 913, found 913;
  • 36
  • [ 873663-50-4 ]
  • 3-iodo-N,N-bis(4-methoxybenzyl)-2-(2-(4-methoxybenzyl)-2H-tetrazol-5-yl)-6-(2-(trimethylsilyl)ethylsulfonyl)benzenesulfonamide [ No CAS ]
  • 2’,3‘-diamino-N,N-bis(4-methoxybenzyl)-2-(2-(4-methoxybenzyl)-2H-tetrazol-5-yl)-4-((2-(trimethylsilyl)ethyl)sulfonyl)-[1,1‘-biphenyl]-3-sulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,4-dioxane; water; at 80℃; for 16.0h;Inert atmosphere; Into a 50 mL round bottom flask was placed 3-(4,4,5,5-tetramethyl-1,3,2- dioxaborolan-2-yl)benzene- 1 ,2-diamine (0.802 g, 3.43 mmol), 3 -iodo-N,N-bis(4- methoxybenzyl)-2-(2-(4-methoxybenzyl)-2H-tetrazol-5 -yl)-6-((2-(trimethylsilyl)ethyl)sulfonyl)benzenesulfonamide (Synthesis described above, 2.0 g, 2.3 mmol), Pd(PPh3)4 (0.528 g, 0.457 mmol) and sodium carbonate (0.726 g, 6.85 mmol) in 1,4-dioxane (6 ml) and water (1.500 ml). The reaction mixture was degassed with nitrogen for 3 times and stirred at 80C for l6hr. The resulting mixture was extracted with ethyl acetate(300 mL) and washed with water(250 mL). Then the organic layer was concentrated under vacuum. The residue was applied on a silica gel column with ethyl acetate/petrol ether (1/1) to give the title compound: LCMS (ESI) calc?d for C42H49N7O7S2Si [M + H]: 856, found 856; ?H NMR (300 MHz, d-DMSO): oe 8.57-8.54(d, J= 8.4 Hz, 1H), 7.92-7.89(d, J= 8.4 Hz, 1H), 7.06-6.73(m, 13H), 6.52-6.39(m, 1H), 6.23-6. 10(m, 1H),4.79-4.45(m, 2H), 4.30-4.1 1(m, 2H),4.08-3.88(m, 4H), 3.724(s, 12H), 1.09-0.80(m, 2H), 0.029(s, 9H).
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