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Chemical Structure| 380430-57-9 Chemical Structure| 380430-57-9

Structure of 380430-57-9

Chemical Structure| 380430-57-9

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Product Details of [ 380430-57-9 ]

CAS No. :380430-57-9
Formula : C7H10BNO4S
M.W : 215.04
SMILES Code : OB(C1=CC=C(NS(=O)(C)=O)C=C1)O
MDL No. :MFCD02179473
InChI Key :NDVJJEADFLTFCD-UHFFFAOYSA-N
Pubchem ID :2773537

Safety of [ 380430-57-9 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of [ 380430-57-9 ]

* 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 [ 380430-57-9 ]

[ 380430-57-9 ] Synthesis Path-Downstream   1~35

  • 1
  • [ 380430-57-9 ]
  • [ 374927-11-4 ]
  • <i>N</i>-{4-[5-(3-benzo[1,3]dioxol-5-yl-9-oxo-1,3,4,9-tetrahydro-pyrrolo[3,4-<i>b</i>]quinoline-2-carbonyl)-furan-2-yl]-phenyl}-methanesulfonamide [ No CAS ]
  • 2
  • C19H26BrFN2O3 [ No CAS ]
  • [ 380430-57-9 ]
  • C26H34FN3O5S [ No CAS ]
  • 3
  • [ 897040-21-0 ]
  • [ 380430-57-9 ]
  • <i>N</i>-{4-[9-isopropyl-6-(2-methoxy-ethylamino)-9<i>H</i>-purin-2-yl]-phenyl}-methanesulfonamide [ No CAS ]
  • 4
  • [ 910221-33-9 ]
  • [ 380430-57-9 ]
  • 4'-Methanesulfonylamino-biphenyl-4-carboxylic acid methyl-{(S)-1-[(S)-3-(3-phenyl-propylamino)-pyrrolidine-1-carbonyl]-pyrrolidin-3-yl}-amide [ No CAS ]
  • 5
  • [ 890315-72-7 ]
  • [ 380430-57-9 ]
  • [ 910240-97-0 ]
YieldReaction ConditionsOperation in experiment
With sodium hydrogencarbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; water; toluene; for 4.5h;Heating / reflux; To toluene 24mL solution of tert-butyl 4-bromo-2-nitrobenzoate 3.0g were added ethanol 9.0mL, water 4.5mL, 4-N-(methanesulfonamide)phenylboronic acid 2.6g, sodium hydrogen carbonate 2.1g and tetrakis(triphenylphosphine)palladium(0) 0.57g, and it was heated and refluxed under nitrogen atmosphere for 4 hours and 30 minutes. After the reaction mixture was cooled to room temperature, ethyl acetate and water were added to it. After insoluble matter was filtrated, the organic layer was separated and collected, dried over anhydrous magnesium sulfate after washing with saturated sodium chloride aqueous solution, and the solvent was removed under reduced pressure. Hexane and diisopropyl ether were added to the obtained residue, solid matter was filtrated to give tert-butyl 4-(4-N-(methanesulfonamido)phenyl)-2-nitrobenzoate 3.9g of white solid. 1H-NMR(DMSO-d6) delta value: 1.51(9H,s),3.06(3H,s),7.32-7.37(2H,m),7.79-7.84(2H,m),7.89(1H,d,J=8.2Hz),8.07(1H,dd,J=8.2,1.8Hz),8 .23(1H,d,J=1.8Hz),10.02-10.08(1H,broad).
  • 6
  • [ 862730-04-9 ]
  • [ 380430-57-9 ]
  • N-[4-(4-Amino-1-isopropyl-1H-pyrazolo[3,4-d]pyrimidin-3-yl)-phenyl]-methanesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
3% With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; ethanol; water; at 80℃; Synthesis of N-[4-(4-Amino-1-isopropyl-1H-pyrazolo[3,4-d]pyrimidin-3-yl)-phenyl]-methanesulfonamide (BA40); A solution of 4-Methanesulfonylaminophenylboronic acid (24 mg, 0.11 mmol) in EtOH (3.3 ml) was added to a solution of 3-iodo-1-isopropyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine (30 mg, 0.10 mmol) in DME (12 ml). Pd(PPh3)4 (30 mg, 0.03 mmol) and saturated Na2CO3 (1.9 ml) were added and the reaction was heated to 80 C. under an argon atmosphere overnight. After cooling, the reaction was extracted with saturated NaCl and CH2Cl2. Organic phases were combined, concentrated in vacuo and purified by RP-HPLC (MeCN:H2O:0.1% TFA) to yield BA40 (0.9 mg, 3% yield). ESI-MS (M+H)+ m/z calcd 347.1, found 347.0.
  • 7
  • [ 1013635-00-1 ]
  • [ 380430-57-9 ]
  • 3-{4-[(methylsulfonyl)amino]phenyl}-7-({2-[4-(trifluoromethyl)phenyl](1,3-thiazol-5-yl)}methoxy)chromen-4-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium carbonate;bis-triphenylphosphine-palladium(II) chloride; In 1,2-dimethoxyethane; water; for 1h;Heating / reflux; To a mixture of 3-iodo-7-({4-methyl-2-[4-(trifluoromethyl)phenyl](1,3-thiazol-5-yl)}methoxy)chromen-4-one (55.0 mg, 0.10 mmol), 4-(dihydroxyboron)-(methylsulfonyl)phenylamine (22.5 mg, 0. 15 mmol), bis-(triphenylphosphine) palladium (II) dichloride(3.5 mg, 0.005 mmol) was added dimethoxyethane (2 ml) and aqueous sodium carbonate solution (2M, 0.1 ml, 2 equivs). The mixture was refluxed for 1 hour, cooled to ambient temperature, filtered through celite (3 g), and the celite washed with ethyl acetate (50 ml). The filtrate was washed with brine (30 ml), and dried over sodium sulfate. The solvent was removed under reduced pressure, and the residue chromatographed on silica gel, eluting with ethyl acetate/hexanes 50/1, after which the product was crystallized from ethyl acetate (3 ml), to provide 3-{4-[(methylsulfonyl)amino]phenyl}-7-({2-[4-(trifluoromethyl)phenyl](1,3-thiazol-5-yl)}methoxy)chromen-4-one.
  • 8
  • [ 1014612-91-9 ]
  • [ 380430-57-9 ]
  • 1,1-dimethylethyl (4-{4-[(methylsulfonyl)amino]phenyl}-1H-pyrrolo[2,3-b]pyridin-2-yl)acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium carbonate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,4-dioxane; water; at 180℃; for 0.05h;Microwave irradiation; 1,1 -Dimethylethyl (4-bromo-1/-/-pyrrolo[2,3-o]pyridin-2-yl)acetate (0.311g, 1mmol), {4- [(methylsulfonyl)amino]phenyl}boronic acid (0.32Og, 1.5mmol), sodium carbonate (0.09Og) and bis(diphenylphosphino)ferrocene palladium (II) chloride (0.026g) were mixed in dioxan/water (5:1, 3ml). The mixture was heated in the Biotage Initiator mw at 18O0C for 3 mins. The mixture was separated between DCM (50ml) and water (10ml). The organic phase was evaporated and purified by silica SPE cartridge eluting with EtOAc/DCM (0- 50%) over an hour. The main fraction was evaporated to give the title compound as a mustard coloured crystalline solid (0.301 g). MH+402, rt= 3.0 mins
  • 9
  • [ 1014613-12-7 ]
  • [ 380430-57-9 ]
  • N-methyl-2-(4-{4-[(methylsulfonyl)amino]phenyl}-1H-pyrrolo[2,3-b]pyridin-2-yl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium carbonate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,4-dioxane; water; at 180℃; for 0.05h;Microwave irradiation; 2-(4-Bromo-1 H-pyrrolo[2,3-b]pyridin-2-yl)-lambda/-methylacetamide (0.14mmol), {4-[(methylsulfonyl)amino]phenyl}boronic add (0.045g, 0.21 mmol), sodium carbonate (0.014g) and bis(diphenylphosphino)ferr?cene palladium (II) chloride (0.004g) were treated with dioxan/water (5:1 , 1ml). The mixture was heated in the Biotage Initiator mw at 180 0C for 3 mins. The reaction was diluted with DCM (15ml) and washed with water (5ml). The organic phase was evaporated and purified by MDAP. The main peak was evaporated to give the title compound as a cream solid (0.005g). MH+359, rt= 2.26 mins
  • 10
  • [ 1014613-11-6 ]
  • [ 380430-57-9 ]
  • N,N-dimethyl-2-(4-{4-[(methylsulfonyl)amino]phenyl}-1H-pyrrolo[2,3-b]pyridin-2-yl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium carbonate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,4-dioxane; water; at 180℃; for 0.05h;Microwave irradiation; 2-(4-Bromo-1/-/-pyrrolo[2,3-/3]pyridin-2-yl)-lambda/,lambda/-dimethylacetamide (0.14mmol), {4- [(methylsulfonyl)amino]phenyl}boronic acid (0.045g, 0.21 mmol), sodium carbonate (0.014g) and bis(diphenylphosphino)ferrocene palladium (II) chloride (0.004g) were treated with dioxan/water (5:1 , 1ml). The mixture was heated in the Biotage Initiator mw at 180 0C for 3 mins. The reaction was diluted with DCM (15ml) and washed with water <n="178"/>(5ml). The organic phase was evaporated and purified by MDAP. The main peak was evaporated to give the title compound as a brown gum (0.014g). MH+373, rt= 2.33 mins
  • 11
  • [ 928656-45-5 ]
  • [ 380430-57-9 ]
  • 6'-amino-4-[(methylsulfonyl)amino]-1,1':3',1"-terphenyl-5'-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium carbonate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In 1,4-dioxane; water; at 150℃; for 0.333333h;Microwave irradiation; Example 31 6'-Amino-4-[(methylsulfonyl)amino]-1 ,1 ':3',1 "-terphenyl-51- carboxamide; 4-Amino-5-bromo-3-biphenyl-carboxamide (Intermediate 7, 48 mg, 0.17 mmol), {4- [(methylsulfonyl)amino]phenyl}boronic acid (53 mg, 0.25 mmol), sodium carbonate (105 mg, 0.99 mmol) and dichloro(1 ,1 l-bis-(diphenylphosphino)-ferrocene)palladium(ll)- dichloromethane adduct (12 mg, 0.016 mmol) were slurried with 1 ,4-dioxane (1 mL) and water (1 mL). The mixture was heated with stirring in a microwave reactor at 150 0C for 20 EPO <DP n="79"/>mins. The cooled mixture was filtered through a 5g silica cartridge, eluting with methanol (10 ml_). After concentration in-vacuo, purification by mass-directed HPLC yielded the title compound (43 mg) as an off-white solid.MS [M+1]+ 382.13; 1H NMR delta» (400.13 MHz, Cf6-DMSO, TMS): 9.84 (br s, 1H), 8.08 (br s, 1 H), 7.88 (d, J = 1.8 Hz, 1 H), 7.68 (d, J = 7.3Hz, 2H), 7.45-7.38 (m, 5H), 7.32-7.24 (m, 4H), 6.33 (br s, 2H), 3.05 (s, 3H).
  • 12
  • [ 928656-38-6 ]
  • [ 380430-57-9 ]
  • 4'-amino-4-chloro-4"-[(methylsulfonyl)amino]-1,1':3',1"-terphenyl-5'-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium carbonate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In 1,4-dioxane; water; at 150℃; for 0.333333h;Microwave irradiation; Example 40 : 4l-Amino-4-chloro-4"-[(methylsulfonyl)amino]-1,1i:3',1"-terphenyl-5I- carboxamide; 4-amino-5-bromo-4'-chloro-3-biphenyl-carboxamide (Intermediate 4, 31 mg, 0.1 mmol), <strong>[380430-57-9]{4-[(methylsulfonyl)amino]phenyl}boronic acid</strong> (22 mg, 0.1 mmol), sodium carbonate (61 mg, 0.58 mmol) and dichloro(1 ,1'-bis-(diphenylphosphino)ferrocene)palladium(ll)- dichloromethane adduct (7 mg, 0.01 mmol) were slurried with 1 ,4-dioxane (1 mL) and water (1 mL). The mixture was heated with stirring in a microwave reactor at 150 0C for 20 mins. The cooled mixture was filtered through a silica cartridge (500 mg silica), rinsing with MeOH, and the eluent concentrated in vacuo. The resulting crude solid was dissolved in 1 :1 DMSO / MeOH, and purified by preparative HPLC using a 30-80% MeCN (aq) gradient. Fractions corresponding to the desired product were identified by LCMS, and passed through an aminopropyl functionalised silica cartridge (1 g sorbent, pre- equilibrated with methanol, 2 column volumes), eluting with methanol. Concentration in vacuo yielded the title compound (14.6 mg) as a white solid.MS [M+1]+416.11 / 418.10 (approximately 3:1 ratio); 1H NMR delta* (400.13 MHz, cfe-DMSO, TMS): 8.09 (br s, 1 H), 7.89 (d, J = 2.0 Hz, 1 H), 7.73 (d, J = 8.5 Hz, 2H), 7.44 (d, J = 6.8 Hz, 2H), 7.42 (d, J = 6.5 Hz, 2H), 7.38 (d, J = 2.0 Hz, 1 H), 7.31 (s, 2H), 7.29 (s, 1 H), 6.39 (br s, 2H), 3.03 (s, 3H).
  • 13
  • [ 928657-11-8 ]
  • [ 380430-57-9 ]
  • C21H20N2O4S [ No CAS ]
  • 14
  • C16H12IN3O [ No CAS ]
  • [ 380430-57-9 ]
  • C23H20N4O3S [ No CAS ]
  • 15
  • [ 867256-58-4 ]
  • [ 380430-57-9 ]
  • N-[4'-(2-(S)-pyrrolidin-1-ylmethyl-pyrrolidine-1-carbonyl)-biphenyl-4-yl]-methanesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water; at 90℃; for 0.5h;CEM microwave reactor; In a microwave reactor vessel, place (4-bromo-phenyl)-(2-(S)-pyrrolidin- l-ylmethyl-pyrrolidin-yl)methanone (l.Ommol), 4-methylsulfonamidephenyl boronic acid (1.5mmol), tetrakis- (triphenylphosphine) palladium (0.044mmol), dioxane (0.10M) and 2M aqueous sodium carbonate (5.0mmol) and run in a CEM microwave reactor for 30 minutes at 90C with 20W power and cooling on. After this time, concentrate the reaction in vacuo. Purify the title compound via radial chromatography eluting with 2M ammonia in methanol and dichloromethane. MS (m/e): 428.2 (M+l)
With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water; at 90℃; for 0.5h;Microwave irradiation (20 W); Example 32N-[4'-(2-(S)-Pyrrolidin-1-ylmethyl-pyrrolidine-1-carbonyl)-biphenyl-4-yl]-methanesulfonamide Procedure FF: In a microwave reactor vessel, place (4-bromo-phenyl)-(2-(S)-pyrrolidin-1-ylmethyl-pyrrolidin-yl)methanone (1.0 mmol), 4-methylsulfonamidephenyl boronic acid (1.5 mmol), tetrakis-(triphenylphosphine) palladium (0.044 mmol), dioxane (0.10M) and 2M aqueous sodium carbonate (5.0 mmol) and run in a CEM microwave reactor for 30 minutes at 90 C. with 20 W power and cooling on. After this time, concentrate the reaction in vacuo. Purify the title compound via radial chromatography eluting with 2M ammonia in methanol and dichloromethane. MS (m/e): 428.2 (M+1)
  • 16
  • [ 124-63-0 ]
  • [ 214360-73-3 ]
  • [ 380430-57-9 ]
  • 17
  • [ 928657-11-8 ]
  • [ 380430-57-9 ]
  • 6'-hydroxy-4-[(methylsulfonyl)amino]-1,1':3',1"-terphenyl-5'-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Example 2 : e'-Hydroxy^-'mefnyisuifonyOaminoj-i.i'iS'.r'-terphenyi-S'- carboxamide; A mixture of 5-bromo-4-(methyloxy)-3-biphenylcarboxamide (Intermediate 4, 25 mg, 0.08 mmol), <strong>[380430-57-9]{4-[(methylsulfonyl)amino]phenyl}boronic acid</strong> (26 mg, 0.12 mmol), sodium carbonate (52 mg, 0.49 mmol) and dichloro(1 ,1'- bis(diphenylphosphino)ferrocene)palladium(ll)-dichloromethane adduct (6 mg, 0.003 mmol) in 1 ,4-dioxane (1 mL) and water (1 mL) was heated with stirring in a microwave reactor at 150 0C for 20 mins. MeOH (5 mL) was added and the mixture was filtered through a silica cartridge (500 mg silica), eluting with MeOH (10 mL), and the eluent concentrated in vacuo. Pyridine (2 mL) and lithium iodide (55 mg) were added to the EPO <DP n="121"/>resulting solid, and the mixture was heated with stirring in a microwave reactor at 175 0C for 2 h. After concentration in vacuo, water (5 mL) was added to the resulting crude solid, and the mixture sonicated. Concentrated hydrochloric acid (37%, 0.5 mL) was added, and the crude solid was isolated by filtration. After dissolution in 1 :1 DMSO / methanol solution (1 mL), purification by preparative HPLC using a 30-80 % MeCN (aq) gradient yielded the title compound (15.6 mg, 0.04 mmol) as a brown solid.MS [M+1]+ 383.30; 1H NMR ^ (400.13 MHz, cfe-DMSO, TMS): 13.97 (s, 1H), 9.83 (s, 1H), 8.76 (br s, 1 H), 8.20 (d, J = 2.0 Hz, 1 H), 8.09 (br s, 1 H), 7.77 (s, 1 H), 7.75 (d, J = 1.3 Hz1 2H), 7.64 (d, J = 8.5 Hz, 2H), 7.46 (t, J = 7.7 Hz, 2H), 7.34 (t, J = 7.3 Hz, 1 H), 7.28 (d, J = 8.8 Hz, 2H), 3.03 (s, 3H).
  • 18
  • [ 1025959-29-8 ]
  • [ 380430-57-9 ]
  • 4'-amino-4-fluoro-4"-[(methylsulfonyl)amino]-1,1':3',1"-terphenyl-5'-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium carbonate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In 1,4-dioxane; water; at 150℃; for 0.333333h;Microwave irradiation; Example 37 : 4l-Amino-4-fluoro-4"-[(methylsulfonyl)amino]-1,1':3l,1"-terphenyl-5>- carboxamide; 4-Amino-5-bromo-4'-fluoro-3-biphenylcarboxamide (Intermediate 13, 53 mg, 0.17 mmol), <strong>[380430-57-9]{4-[(methylsulfonyl)amino]phenyl}boronic acid</strong> (55 mg, 0.26 mmol), sodium carbonate (109 mg, 1.03 mmol) and dichloro(1 ,1'-bis-(diphenylphosphino)-ferrocene)palladium(ll)- dichloromethane adduct (13 mg, 0.017 mmol) were slurried with 1 ,4-dioxane (1 mL) and water (1 mL). The mixture was heated with stirring in a microwave reactor at 150 C for 20 mins. The cooled mixture was diluted with methanol (10 mL), filtered through a silica cartridge (500 mg silica) and the eluent concentrated in vacuo. The crude solid was dissolved in 1:1 DMSO / methanol solution (1 mL), filtered, and purified by preparative HPLC using a 20-60% MeCN (aq) gradient. Fractions corresponding to the desired product were identified by LCMS, and passed through an aminopropyl functionalised silica cartridge (1 g sorbent, pre-equilibrated with methanol, 2 column volumes), eluting with methanol. Concentration in vacuo yielded the title compound (33.4 mg) as a white solid.MS [M+1]+ 400.14; 1H NMR delta» (400.13 MHz, CZ6-DMSO, TMS): 9.86 (br s, approximately 1 H), 8.07 (br s, 1 H), 7.84 (s, 1 H), 7.72 (dd, J = 8.5, 5.5 Hz, 2H), 7.43 (d, J = 8.5 Hz, 2H),] EPO <DP n="83"/>7.35 (d, J = 1.8 Hz, 1 H), 7.33-7.24 (m, 3H), 7.22 (t, J = 8.9 Hz, 2H), 6.33 (br s, 2H), 3.04 (br s, 3H).
  • 19
  • [ 928656-36-4 ]
  • [ 380430-57-9 ]
  • 2-amino-4'-[(methylsulfonyl)amino]-5-(4-pyridinyl)-3-biphenylcarboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
55% With sodium carbonate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In 1,4-dioxane; water; at 150℃; for 0.333333h;Microwave irradiation; Example 34 2-Amino-4'-[(methylsulfonyl)amino]-5-(4-pyridinyl)-3- biphenylcarboxamide; 2-Amino-3-bromo-5-(4-pyridinyl)benzamide (Intermediate 16, 50 mg, 0.17 mmol), {4- [(methylsulfonyl)amino]phenyl}boronic acid (56 mg, 0.26 mmol), sodium carbonate (109 mg, 1.03 mmol) and dichloro(1 ,1'-bis-(diphenylphosphino)-ferrocene)palladium(ll)- dichloromethane adduct (12 mg, 0.017 mmol) were slurried with 1 ,4-dioxane (1 ml.) and water (1 ml_). The mixture was heated with stirring in a microwave reactor at 150 0C for 20 mins. The cooled mixture was diluted with methanol (10 ml_), filtered through a silica cartridge (500 mg silica) and the eluent concentrated in vacuo. The crude solid was dissolved in 1 :1 DMSO / methanol solution (1 ml_), filtered, and purified by preparative HPLC using a 0-35 % MeCN (aq) gradient. Fractions corresponding to the desired product were identified by LCMS, combined, passed through an aminopropyl functionalised silica cartridge (pre-equilibrated with methanol, 500 mg sorbent) and concentrated to afford the title compound as a white solid (34.6 mg, 55 %).MS [M+1]+ 383.12; 1H NMR Sn (400.13 MHz, cfe-DMSO, TMS): 9.88 (br s, 1 H), 8.53 (d, J = 6.0 Hz1 2H), 8.14 (br s, 1 H), 8.05 (d, J = 2.0 Hz, 1 H)1 7.74 (d, J = 6.0 Hz, 2H), 7.54 (d, J = 2.0 Hz1 1 H), 7.43 (d, 2H, J = 8.5 Hz), 7.36 (b. s, 1 H)1 7.32 (d, J = 8.5 Hz, 2H), 6.59 (b. s, 2H)1 3.04 (S1 3H).
  • 20
  • [ 928775-00-2 ]
  • [ 380430-57-9 ]
  • 1,1-dimethylethyl 2-{4-[(methylsulfonyl)amino]phenyl}-4,5,7,8-tetrahydropyrazolo[3,4-d]azepine-6(2H)-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With pyridine; oxygen; copper diacetate; In dichloromethane; at 20℃;Molecular sieve; Description 39; 1,1-Dimethylethyl 2-{4-[(methylsulfonyl)amino]phenyl}-4,5,7,8- tetrahydropyrazolo[3,4-d]azepine-6(2H)-carboxylate (D39); To <strong>[380430-57-9]{4-[(methylsulfonyl)amino]phenyl}boronic acid</strong> (commercially available from e.g. Combi-Blocks) (127mg, 0.29mmol) in dichloromethane (3ml) was added copper(ll) acetate (107mg, 0.59mmol) and 4A molecular sieves (190mg), and the reaction stirred at room temperature, open to air, for 10 minutes. 1 ,1-Dimethylethyl 4,5,7,8- tetrahydropyrazolo[3,4-c/]azepine-6(2/-/)-carboxylate (may be prepared as described in Description 9) (70mg, 0.29mmol) was added and the reaction stirred at room temperature, open to air, overnight. The reaction mixture was diluted with methanol and filtered through a celite pad, washing with methanol. Solvent was evaporated in vacuo. Ethyl acetate and water were added, and the product was extracted into ethyl acetate (x3), washed with water (x1 ), then saturated sodium bicarbonate solution (x1 ), and then dried over magnesium sulfate. Solvent was evaporated in vacuo. The resulting crude product was purified by column chromatography on silica gel, eluting with a mixture of ethyl acetate in hexane (0-50%). Relevant fractions were combined and solvent evaporated in vacuo. The resulting crude product was purified further by Mass Directed Autopreparation to afford the title compound (D39). MS (ES+) m/e 407 [M+H]+.
  • 21
  • [ 116632-33-8 ]
  • [ 380430-57-9 ]
  • [ 959932-00-4 ]
  • 22
  • [ 3934-20-1 ]
  • [ 380430-57-9 ]
  • [ 1056636-13-5 ]
YieldReaction ConditionsOperation in experiment
61% With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In propan-1-ol; water; toluene; at 100℃; for 66h; A round bottomed flask was charged with 4-methanesulfonylaminophenylboronic acid (4.3Og, 20 mmol) and 2,4-dichloropyrimidine (5.97 g, 40 mmol, 2 eq), toluene (75 mL), n- propanol (25 mL) and 2 M sodium carbonate solution (18 mL, 1.8 eq). The reaction vessel was then evacuated and backfilled with nitrogen three times before adding tetrakis(triphenylphosphine) palladium (0) catalyst (1.02 g, 4.4 mol%). The reaction vessel was again evacuated and backfilled with nitrogen three times before being heated at 100C under a nitrogen atmosphere for 66 hours. The reaction mixture was then cooled and stirred at room temperature for several hours during which time the product precipitated from the reaction mixture. The fine yellow solid (3.45 g, 61% yield) was collected by vacuum filtration washed with methanol and dried under high vacuum. 1H NMR and LC MS data confirmed this to be the desired iV-(4-(2-chloropyrimidin-4- yl)phenyl)methanesulfonamide. 1H NMR t°-DMSO, 300 MHz) delta 10.26 (IH, brs), 8.75 (IH, d, J= 5.5 Hz)5 8.17 (2H, d, J= 9.1 Hz), 8.05 (IH, d, J= 5.5 Hz), 7.35 (2H, d, J= 8.7 Hz), 3.10 (3H5 s). LC-MS: rt 5.54 min (br) m/z 284.2/286.1 [M+H]+.
61% With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In propan-1-ol; water; toluene; at 100℃; for 66h; Example 4 - Synthesis of Compound 73A; round bottomed flask was charged with 4-methanesulfonylaminophenylboronic acid (4.30 g, 20 mmol) and 2,4-dichloropyrimidine (5.97 g, 40 mmol, 2 eq.), toluene (75 mL), n-propanol (25 mL) and aqueous sodium carbonate solution (2M, 18 mL, 1.8 eq.). The reaction mixture was evacuated and backfilled with nitrogen three times before adding tetrakis(triphenylphosphine) palladium (0) catalyst (1.02 g, 4.4 mol%). The reaction mixture was again evacuated and backfilled with nitrogen three times before being heated at 100C under a nitrogen atmosphere for 66 hours. The reaction mixture was cooled and stirred at room temperature for several hours during which time the product precipitated from the reaction mixture. The fine yellow solid (3.45 g, 61% yield) was collected by vacuum filtration, washed with methanol and dried under high vacuum. 1H NMR and LC MS data confirmed this to be the desired N-(4-(2-chloropyrimidin-4- yl)phenyl)methanesulfonamide. 1H NMR (300 MHz,
  • 23
  • [ 845889-22-7 ]
  • [ 380430-57-9 ]
  • C23H31N5O6S2 [ No CAS ]
  • 24
  • [ 74877-08-0 ]
  • [ 380430-57-9 ]
  • [ 1100768-30-6 ]
YieldReaction ConditionsOperation in experiment
54% With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In acetonitrile; at 100℃; for 0.5h;microwave; To a solution of (S)- 1-(3-bromo-phenyl)-ethylamine (100 mg, 0.50 mmol) in ACN (1.6 ml) were added [(4-methylsulfonyl)aminophenyl]boronic acid (108 mg, 0.50 mmol), sodium carbonate (53 mg, 0.50 mmol), water (0.5 ml) and tetrakis(triphenyl- 5 phosphine)palladium(O). The reaction mixture was heated 30 min at 1000C using microwaves. The mixture was filtered and purified by preparative HPLC. The relevant fractions were lyophilized to give 110 mg (yield: 54%) of the desired product.
  • 25
  • [ 1155287-65-2 ]
  • [ 380430-57-9 ]
  • [ 1155286-36-4 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate;bis(eta3-allyl-mu-chloropalladium(II)); 1,5-bis-(diphenylphosphino)pentane; In N,N-dimethyl-formamide; at 80℃; for 24h; To a solution of (62) (190 mg, 0.48 mmole), 3-chlorophenyl boronic acid (157 mg, 0.73 mmole), K2CO3 (153 mg, 1.1 mmole), [Pd(n3-C3H5)Cl]2 (9 mg, 0.024 mmole), 1,5-bis(diphenylphosphino)pentane (22 mg, 0.048 mmole) in 1.5 mL anhydrous DMF was heated at 80 C. for 24 hrs. The reaction was diluted with 5 mL water and extracted 3× with ethyl acetate. Combined organic layers were washed with water, brine, dried over Na2SO4, filtered and concentrated to give 200 mg crude. Purification by silica gel prep plate gave 10 mg white solid BA-20. 1H-NMR (400 MHz, DMSO)
  • 26
  • [ 824-94-2 ]
  • [ 380430-57-9 ]
  • [ 1154417-76-1 ]
YieldReaction ConditionsOperation in experiment
96% With potassium carbonate;palladium diacetate; triphenylphosphine; In 1,2-dimethoxyethane; ethanol; water; at 90℃; for 48h; A round bottom was charged with 4-methanesulfonamide phenyl boronic acid (6.5 mmol), Pd(OAc)2 (0.5 mmol, 112 mg), PPh3 (mumol, 262 mg), K2CO3 (7.5 mmo, 1.03 g), DME (50 mL), water (5 mL), ethanol (5 mL) and 4-methoxy benzyl chloride (7). The reaction mixture was immersed in a 90 C. bath and was stirred under N2 for 48 h. Then the reaction was cooled to rt and poured into a beaker with water (100 mL). A cream solid precipitated out. The solid was collected and purified by flash silica gel column chromatography. The column was eluted with hexane/EtOAc (2:1) to give compound (8) 1.4 g (96% yield) as a white solid.
  • 27
  • [ 1152473-40-9 ]
  • [ 380430-57-9 ]
  • [ 1152473-64-7 ]
YieldReaction ConditionsOperation in experiment
60% With water; sodium hydrogencarbonate;tetrakis(triphenylphosphine) palladium(0); In N,N-dimethyl-formamide; at 100℃; for 15h; To a solution of Compound 1 (lOOmg, 0.228mmol) and N-4- methanesulfonamide phenylboronic acid (74mg, 0.34mmol) in DMF (3mL) were added 2M aq. NaHCO3 (350muL) and Pd[PPh3]4 (26mg, 0.02mmol). The reaction was heated at 1000C for 15 h, allowed to cool, and then diluted with water (2OmL). The resultant precipitate was collected by filtration and air-dried. The crude product was re-dissolved in hot methanol/DMF, filtered hot, and then sufficient water was added to cause the solution to become cloudy. After cooling to room temperature and then further in an ice-bath, the solid was collected by filtration, washed with water and air-dried, followed by further drying under reduced pressure. This provided Compound 14 as a yellow/green solid (66mg, 60%).
  • 28
  • [ 1013635-00-1 ]
  • [ 380430-57-9 ]
  • 3-{4-[(methylsulfonyl)amino]phenyl}-7-({4-methyl-2-[4-(trifluoromethyl)phenyl](1,3-thiazol-5-yl)}methoxy)chromen-4-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium carbonate;bis-triphenylphosphine-palladium(II) chloride; In 1,2-dimethoxyethane; water; for 1h;Reflux; Step 2 - Preparation of a Compound of Formula I in which R1 is Phenyl1(l,3-thiazol-5- yl), R is 4-Methylsulfonamide, R is Hydrogen, V is Oxygen, X, Y, and Z are -CH-, and W is Methylene <n="60"/>[0171] To a mixture of 3-iodo-7-({4-methyl-2-[4-(trifluoromethyl)phenyl](l,3-thiazol- 5-yl)}methoxy)chromen-4-one (55.0 mg, 0.10 mmol), 4-(dihydroxyboron)- (methylsulfonyl)phenylamine (22.5 mg, 0.15 mmol), bis-(triphenylphosphine) palladium (II) dichloride(3.5 mg, 0.005 mmol) was added dimethoxyethane (2 ml) and aqueous sodium carbonate solution (2M, 0.1 ml, 2 equivs). The mixture was refluxed for 1 hour, cooled to ambient temperature, filtered through celite (3 g), and the celite washed with ethyl acetate (50 ml). The filtrate was washed with brine (30 ml), and dried over sodium sulfate. The solvent was removed under reduced pressure, and the residue chromatographed on silica gel, eluting with ethyl acetate/hexanes 50/1, after which the product was crystallized from ethyl acetate (3 ml), to provide 3-{4- [(methylsulfonyl)amino]phenyl}-7-({2-[4-(trifluoromethyl)phenyl](l,3-thiazol-5- yl)} methoxy)chromen-4-one.
  • 29
  • [ 1149733-95-8 ]
  • [ 380430-57-9 ]
  • C25H20FN5O4S [ No CAS ]
  • 30
  • 3-[4-bromo-5-(3-methoxyprop-1-ynyl)thiophen-2-yl]-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile [ No CAS ]
  • [ 380430-57-9 ]
  • [ 98-80-6 ]
  • N-{4-[5-(5-cyano-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridin-3-yl)-2-phenylthien-3-yl]phenyl}methanesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
To 3-[4-Bromo-5-(3-methoxy-prop-1-ynyl)-thiophen-2-yl]-4-hydroxy-6-oxo-6,7-dihydro-thieno[2,3-b]pyridine-5-carbonitrile (150 mg, 0.31 mmol, Example 183a) and MgO (43.0 mg, 1.07 mmol) in dioxane (1.25 ml) in DMF (1.25 ml) was added H2O (0.351 ml) and the mixture was stirred for 10 min and then degassed with N2 for 2 min. Phenylboronic acid (42.0 mg, 0.31 mmol), Cs2CO3 (226 mg, 0.70 mmol) and Pd(PPh3)4 (20.0 mg, 0.017 mmol) were added, the vessel flushed with N2, and then stirred at 70 C. for 2 h. Then p-methanesulfonylamide boronic acid (135 mg, 0.62 mmol) was added and the temperature was adjusted to 95 C. and the reaction was stirred for an additional 5 h. The reaction was cooled to rt and overwhelmed with MeOH, filtered and the filtrate was concentrated to give a brown oil. The residue was taken up in DMSO:MeOH (1:1) and purified by RP-HPLC to give the title compound. MS (ESI) m/z 520.0 (M+H+); 1H NMR (300 MHz, DMSO-d6) delta ppm 9.82 (s, 1H), 7.45-7.10 (m, 11H), 3.02 (s, 3H).
  • 31
  • [ 844500-43-2 ]
  • [ 380430-57-9 ]
  • N-{4-[5-(5-cyano-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridin-3-yl)thien-2-yl]phenyl}methanesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
20% A mixture of Example 91c (100 mg, 0.28 mmol), MgO (34 mg, 0.84 mmol) and Cs2CO3 (277 mg, 0.84 mmol) in dioxane (1.2 mL), DMF (1.2 mL) and H2O (0.6 mL) was degassed and stirred at 25 C. for 10 minutes. 4-(Methylsulfonylamino)phenyl boronic acid (80 mg, 0.37 mmol) and Pd(PPh3)4 (13 mg, 0.011 mmol) were added and the reaction mixture was heated at 130 C. for 10 minutes in a microwave reactor. The reaction was cooled to 25 C., diluted with MeOH (10 mL) and filtered. The filtrate was concentrated and purified by RPHPLC on a Waters Symmetry C8 column (25 mm*100 mm, 7 mum particle size) using a gradient of 10% to 100% acetonitrile:0.1% aqueous TFA to provide Example 91D (25 mg, 20%). 1H NMR (300 MHz, DMSO-D6) delta ppm 3.04 (m, 3H) 7.17 (s, 1H) 7.25 (d, J=8.82 Hz, 2H) 7.34 (d, J=4.04 Hz, 1H) 7.38 (d, J=4.04 Hz, 1H) 7.63 (d, J=8.46 Hz, 2H) 9.88 (s, 1H). MS (ESI) m/z 444.0 (M+H)+, 461 (M+NH4)+
  • 32
  • [ 1101173-94-7 ]
  • [ 380430-57-9 ]
  • [ 1198321-17-3 ]
  • 33
  • [ 1200575-51-4 ]
  • [ 380430-57-9 ]
  • [ 1200572-64-0 ]
YieldReaction ConditionsOperation in experiment
25% With potassium carbonate;palladium diacetate; In water; acetonitrile; at 90℃; for 1.5h; EXAMPLE A53Benzyl 4-(6-{4-[(methylsulfonyl)amino]phenyl}-4H-l,3-benzodioxin-2-yl)piperidine-l- carboxylate A suspension of benzyl 4-(6-bromo-4H-l,3-benzodioxin-2-yl)piperidine-l-carboxylate (Intermediate Al; 10 mg, 0.023 mmol), 4-(methanesulfonylamino)phenylboronic acid (5.4 mg, 0.025 mmol), Pd(OAc)2 (2 mg, 0.009 mmol), K2CO3 (8.0 mg, 0.058 mmol) in MeCN (2 mL) and water (0.5 mL) was heated at 90 0C for 1.5 h. The mixture was filtered and then purified by preparative etaPLC (System D). Yield 3.0 mg (25%). Analytical GC: purity 99%; etaRESIMS (ESI+) calcd for C28H30N2O6S 522.1825, found 522.1824.
  • 34
  • [ 1185741-04-1 ]
  • [ 380430-57-9 ]
  • [ 1185741-16-5 ]
  • 35
  • [ 1185741-05-2 ]
  • [ 380430-57-9 ]
  • [ 1185741-17-6 ]
 

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