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[ CAS No. 779335-05-6 ] {[proInfo.proName]}

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Chemical Structure| 779335-05-6
Chemical Structure| 779335-05-6
Structure of 779335-05-6 * Storage: {[proInfo.prStorage]}
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Product Details of [ 779335-05-6 ]

CAS No. :779335-05-6 MDL No. :MFCD09952060
Formula : C11H15BO4S Boiling Point : -
Linear Structure Formula :- InChI Key :YLZRZHOUXZZBTF-UHFFFAOYSA-N
M.W : 254.11 Pubchem ID :53217118
Synonyms :

Calculated chemistry of [ 779335-05-6 ]

Physicochemical Properties

Num. heavy atoms : 17
Num. arom. heavy atoms : 5
Fraction Csp3 : 0.55
Num. rotatable bonds : 2
Num. H-bond acceptors : 4.0
Num. H-bond donors : 1.0
Molar Refractivity : 67.75
TPSA : 84.0 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.09 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 2.48
Log Po/w (WLOGP) : 1.75
Log Po/w (MLOGP) : 0.77
Log Po/w (SILICOS-IT) : 1.91
Consensus Log Po/w : 1.38

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -3.06
Solubility : 0.22 mg/ml ; 0.000864 mol/l
Class : Soluble
Log S (Ali) : -3.89
Solubility : 0.0328 mg/ml ; 0.000129 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.64
Solubility : 0.577 mg/ml ; 0.00227 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 3.22

Safety of [ 779335-05-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302+H312+H332-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 779335-05-6 ]

* 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 [ 779335-05-6 ]

[ 779335-05-6 ] Synthesis Path-Downstream   1~29

  • 1
  • [ 5071-96-5 ]
  • [ 779335-05-6 ]
  • [ 862698-93-9 ]
YieldReaction ConditionsOperation in experiment
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 20℃; for 20h;Product distribution / selectivity; Preparation of N-(3-methoxybenzyl)-5-(4, 4, 5, 5-tetramethyl-1 ,3, 2-dioxaborolan-2-yl)-2- thiophenecarboxamide; A mixture of 5-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)-2-thiophenecarboxylic acid (10.1 g, 39.7 mmol), HOBt (6.43 g, 47.6 mmol), and EDC (9.13 g, 47.6 mmol), in DMF (100 ml_) was treated with 3-methoxybenzylamine (5.6 ml_, 43.7 mmol) and stirred at room temperature for 20 hours. The reaction mixture was poured onto ice water (300 mL) and extracted with EtOAc (3 x 150 ml_). The combined organic layers were washed with brine, dried (MgSO4), filtered and concentrated to afford the product, N-(3-methoxybenzyl)-5-(4,4,5,5-tetramethyl-1 ,3,2-dioxa-borolan-2-yl)-2- thiophenecarboxamide, (12.9 g) as a yellow solid.1 H NMR (400 MHz, DMSO-d6) delta ppm 1.26 (s, 12H), 3.71 (s, 3 H), 4.39 (d, J=6.0 Hz, 2H), 6.78-6.85 (m, 3H), 7.21 (t, J=8.0 Hz, 1 H), 7.51 (d, J=3.7 Hz, 1 H), 7.80 (d, J=3.7 Hz, 1 H), 9.09 (t, J=6.0 Hz, 1 H).
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; for 14h;Product distribution / selectivity; Synthesis of 2; To a solution of 1 (2.0 g, 12 mmol) in THF (20 mL) and toluene (20 mL) was added pinacol (1.4 g, 12 mmol) and the resulting mixture was concentrated under reduced pressure to dryness. The solids obtained was dissolved in THF (20 mL) and toluene(20 mL) and concentrated under reduced pressure two more times. The intermediate solid was dissolved in DMF (40 mL) followed by the addition of EDC (2.3 g, 12 mmol),HOBt (1.6 g, 12 mmol), DIPEA (4.2 mL, 24 mmol) and amine (1.6 g, 12 mmol). The resulting reaction mixture was stirred for 14 h. The reaction mixture was diluted withH2O (50 mL) and ethyl acetate (100 mL). The layers were separated and the organic layer was dried over Na2SO4, filtered and concentrated. The residue was purified by column chromatography (silica gel, 0-50% ethyl acetate/heptane) to obtain 2 as a pale yellow solid (0.37 g, 8.4% for two steps): 1H NMR (500 MHz, DMSO-c/6) delta 9.10 (t, J = 6.0 Hz, 1 H), 7.84 (d, J = 4.0 Hz, 1 H), 7.54 (d, J = 4.0 Hz, 1 H), 7.24 (t, J = 8.0 Hz,1H), 6.88-6.80 (m, 3H), 4.42 (d, J = 6.0 Hz, 2H)1 3.73 (s, 3H), 1.29 (s, 12H).
  • 2
  • [ 779335-05-6 ]
  • [ 89-99-6 ]
  • C18H21BFNO3S [ No CAS ]
YieldReaction ConditionsOperation in experiment
88% With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 20℃; for 20h; Step 2: synthesis of boronate amide intermediates for examples 44 - 55; 5-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)-2-thiophene-carboxylic acid (4.2 g, 16.8 mmol), EDC (2.73 g, 20.16 mmol), and HOBT (3.86 g, 20.16 mmol) were combined in DMF (70 ml_). Aliquots of this solution (5 ml_) were put into test tubes equipped with stir bars. The appropriate amine (1.32 mmol) was added, and the reactions were stirred for 20 hours at room temperature. Each reaction was diluted with EtOAc (30 mL) and H2O (30 mL). The aqueous organic mixture was stirred vigorously and the layers were allowed to separate. The aqueous layer was removed with a pipette. Another aliquot of H2O (20 mL) was added, and the mixture stirred vigorously again. The aqueous layer was once again removed with a pipette. The organic layer was dried (MgSO4), filtered, and concentrated to give the crude products as oils, and were used directly in the next step. Amines used and crude ields obtained:
  • 3
  • 2-carboxythiophene-5-boronic acid [ No CAS ]
  • [ 76-09-5 ]
  • [ 779335-05-6 ]
YieldReaction ConditionsOperation in experiment
75% In toluene; at 110 - 120℃; for 4h; Step (a) - synthesis of 5-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)-2- thiophene-carboxylic acidpinacoltoluene To a solution of 5-(dihydroxyboryl)-2-thiophenecarboxylic acid (4.0 g) in toluene (50 ml) was added pinacol (2.75 g). The reaction mixture was heated at 110-1200C and the water set free during the reaction was continuously removed by a Dean-Stark apparatus. After 4 hours heating, the reaction mixture was cooled down to room <n="68"/>temperature thus providing 5-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)-2-thiophene- carboxylic acid as a white solid which was filtered off (4.43 g, yield : 75%) and used as such for further reaction. The pure compound was characterized by its 1H NMR spectrum (300MHz, CD3OD) as follows: peaks at 1.42 (12H, s), 7.63 (1 H, d) and 7.89 (1 H, d) ppm.
In tetrahydrofuran; toluene; (a) Preparation of 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-thiophenecarboxylic acid; 2-Carboxy-5-thiopheneboronic acid (1.04 g, 6.05 mmol) and pinacol (0.715 g, 6.05 mmol) were dissolved in a mixture of THF (15 mL) and toluene (15 mL). The volatiles were removed by rotary evaporation under reduced pressure. The solids were again treated three times with THF: toluene (10 mL:10 mL) followed by evaporation after each time to give 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-thiophene-carboxylic acid (1.43 g) as a white solid.1H NMR (400 MHz, DMSO-d6) delta ppm 1.27 (s, 12H), 7.51 (d, J=3.6 Hz, 1H), 7.71 (d, J=3.7 Hz, 1H), 13.26 (brs, 1H).
In tetrahydrofuran; toluene;Product distribution / selectivity; Preparation of 5-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)-2-thiophenecarboxylic acid; 2-Carboxy-5-thiopheneboronic acid (1.04 g, 6.05 mmol) and pinacol (0.715 g, 6.05 mmol) were dissolved in a mixture of THF (15 mL) and toluene (15 mL). The volatiles were removed by rotary evaporation under reduced pressure. The solids were again treated three times with THF : toluene (10 mL:10 mL) followed by evaporation after EPO <DP n="38"/>each time to give 5-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)-2-thiophene- carboxylic acid (1.43 g) as a white solid.1 H NMR (400 MHz, DMSO-d6) delta ppm 1.27 (s, 12H), 7.51 (d, J=3.6 Hz, 1 H), 7.71 (d, J=3.7 Hz, 1 H), 13.26 (br s, 1 H).; Synthesis of 2; To a solution of 1 (2.0 g, 12 mmol) in THF (20 mL) and toluene (20 mL) was added pinacol (1.4 g, 12 mmol) and the resulting mixture was concentrated under reduced pressure to dryness. The solids obtained was dissolved in THF (20 mL) and toluene(20 mL) and concentrated under reduced pressure two more times. The intermediate solid was dissolved in DMF (40 mL) followed by the addition of EDC (2.3 g, 12 mmol),HOBt (1.6 g, 12 mmol), DIPEA (4.2 mL, 24 mmol) and amine (1.6 g, 12 mmol). The resulting reaction mixture was stirred for 14 h. The reaction mixture was diluted withH2O (50 mL) and ethyl acetate (100 mL). The layers were separated and the organic layer was dried over Na2SO4, filtered and concentrated. The residue was purified by column chromatography (silica gel, 0-50% ethyl acetate/heptane) to obtain 2 as a pale yellow solid (0.37 g, 8.4% for two steps): 1H NMR (500 MHz, DMSO-c/6) delta 9.10 (t, J = 6.0 Hz, 1 H), 7.84 (d, J = 4.0 Hz, 1 H), 7.54 (d, J = 4.0 Hz, 1 H), 7.24 (t, J = 8.0 Hz,1H), 6.88-6.80 (m, 3H), 4.42 (d, J = 6.0 Hz, 2H)1 3.73 (s, 3H), 1.29 (s, 12H).
  • 4
  • [ 779335-05-6 ]
  • [ 765-30-0 ]
  • [ 1036386-65-8 ]
YieldReaction ConditionsOperation in experiment
87% Step (b) - synthesis of N-(cyclopropyl)-5-(4,4,5,5-tetramethyl-1 ,3,2-c/ioxaborolan- 2-yl)-2-thiophenecarboxamide; Cyclopropylamine, HOBT, DCCDMF, acetonitrile " To a solution of 5-(4,4,5,5-tetramethyl-1 ,3,2-cfioxaborolan-2-yl)-2-thiophene- carboxylic acid (200 mg) and 1-hydroxybenzotriazole (117 mg, 0.86 mmole) in acetonitrile (5 ml) and N,N-dimethylformamide (0.5 ml) were added dicyclohexyl- carbodiimide (179 mg). The reaction mixture was stirred at room temperature for 2 hours after which cyclopropylamine (0.11 ml, 1.6 mmole) was added at 0cC. The reaction mixture was stirred at room temperature for an additional 20 hours. The solids formed were filtered off and the filtrate was concentrated under reduced pressure yielding crude N-(cyclopropyl)-5-(4,4,5,5-tetramethyl-1 ,3,2-cfioxaborolan-2-yl)-2-thiophenecarboxamide.The crude compound was purified by silica gel flash chromatography, the mobile phase being a 5:95 MeOH/CH2CI2 mixture, resulting in the pure title compound as a white powder (201 mg, yield : 87%) which was characterized by its 1H NMR spectrum(300MHz, CD3OD) as follows: peaks at 0.61 (2H, multiplet), 0.86 (2H, multiplet), 1.34 (12H, s), 2.85 (1 H, multiplet), 6.15 (1 H, s), 7.52 (1 H, d) and 7.55 (1 H, d) ppm.
  • 5
  • [ 527-72-0 ]
  • [ 61676-62-8 ]
  • [ 779335-05-6 ]
  • 6
  • [ 6066-82-6 ]
  • [ 779335-05-6 ]
  • [ 1345692-52-5 ]
  • 7
  • [ 779335-05-6 ]
  • [ 1042131-68-9 ]
  • 8
  • [ 76-09-5 ]
  • C12H20BNO2S [ No CAS ]
  • [ 779335-05-6 ]
  • 9
  • [ 779335-05-6 ]
  • C23H19NO3S [ No CAS ]
  • 10
  • [ 779335-05-6 ]
  • (±)-bethyl 5-[3-(6-amino-5-cyano-4-isopropyl-3-methyl-1,4-dihydropyrano[2,3-c]pyrazol-4-yl)-5-cyanophenyl]thiophene-2-carboxylate [ No CAS ]
  • 11
  • [ 779335-05-6 ]
  • (±)-5-[3-(6-amino-5-cyano-3-methyl-4-isopropyl-2,4-dihydropyrano[2,3-c]pyrazol-4-yl)-5-cyanophenyl]-N-[3-(diethylamino)propyl]thiophene-2-carboxamide [ No CAS ]
  • 12
  • [ 779335-05-6 ]
  • C30H33N7O3S [ No CAS ]
  • 13
  • [ 779335-05-6 ]
  • C26H19N3O2S [ No CAS ]
  • 14
  • [ 779335-05-6 ]
  • (±)-benzyl 5-[3-(6-Amino-5-cyano-3-methyl-4-isopropyl-2,4-dihydropyrano[2,3-c]pyrazol-4-yl)-5-cyanophenyl]thiophene-2-carboxylate [ No CAS ]
  • 15
  • [ 779335-05-6 ]
  • C23H19N5O3S [ No CAS ]
  • 16
  • [ 779335-05-6 ]
  • C25H24N6O2S [ No CAS ]
  • 17
  • [ 779335-05-6 ]
  • (4″RS,2‴RS)-5-[3-(6-Amino-5-cyano-3-methyl-4-isopropyl-2,4-dihydropyrano[2,3-c]pyrazol-4-yl)-5-cyanophenyl]-N-[5-(diethylamino)pent-2-yl]thiophene-2-carboxamide [ No CAS ]
  • 18
  • [ 779335-05-6 ]
  • C30H35N7O2S*2C2HF3O2 [ No CAS ]
  • 19
  • [ 779335-05-6 ]
  • (±)-6-amino-5-cyano-4-[3-cyano-5-(5-[3-(morpholin-4-ium-4-yl)propyl]carbamoyl}thiophen-2-yl)phenyl]-3-methyl-4-isopropyl-2,4-dihydropyrano[2,3-c]pyrazol-1-ium bis-(trifluoroacetate) [ No CAS ]
  • 20
  • [ 779335-05-6 ]
  • (±)-5-[3-(6-amino-5-cyano-3-methyl-4-isopropyl-2,4-dihydropyrano[2,3-c]pyrazol-4-yl)-5-cyanophenyl]-N-[3-(4-methylpiperazin-1-yl)propyl]thiophene-2-carboxamide [ No CAS ]
  • 21
  • [ 779335-05-6 ]
  • (4″RS)-di-tert-butyl N-[(5-[3-(6-amino-5-cyano-3-methyl-4-isopropyl-2,4-dihydropyrano[2,3-c]pyrazol-4-yl)-5-cyanophenyl]thien-2-yl)carbonyl]-L-glutamate [ No CAS ]
  • 22
  • [ 779335-05-6 ]
  • [ 908094-04-2 ]
  • C18H21BO4S [ No CAS ]
  • 23
  • [ 779335-05-6 ]
  • tert-butyl (R)-(4-(aminomethyl)phenethyl)(2-((tert-butyldimethylsilyl)oxy)-2-(8-hydroxy-2-oxo-1,2-dihydroquinolin-5-yl)ethyl)carbamate [ No CAS ]
  • (R)-(5-((4-(2-((tert-butoxycarbonyl)(2-((tert-butyldimethylsilyl)oxy)-2-(8-hydroxy-2-oxo-1,2-dihydroquinolin-5-yl)ethyl)amino)ethyl)benzyl)carbamoyl)thiophen-2-yl)boronic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% Step 5: (R)-(5-((4-(2-((tert-butoxycarbonyl)(2-((tert-butyldimethylsilyl)oxy)-2-(8-hydroxy-2-oxo-1,2-dihydroquinolin-5-yl)ethyl)amino)ethyl)benzyl)carbamoyl)thiophen-2-yl)boronic acid HBTU (100 mg, 0.264 mmol) was dissolved in DMF (0.8 ml) and <strong>[779335-05-6]5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene-2-carboxylic acid</strong> (67.1 mg, 0.264 mmol) was added and the mixture was stirred for ½ h. The reaction was added with (R)-tert-butyl 4-(aminomethyl)phenethyl(2-((tert-butyldimethylsilyl)oxy)-2-(8-hydroxy-2-oxo-1,2-dihydroquinolin-5-yl)ethyl)carbamate (150 mg, 0.264 mmol) and DIPEA (0.138 ml, 0.793 mmol) and the mixture was stirred for 5 hr at rt. After add of water (50 ml) a solid precipitated, the solid was filtered on gooch, then dissolved in ethyl acetate, dried over Na2SO4 and the solvent was evaporated under vacuum to give a white solid of (R)-(5-((4-(2-((tert-butoxycarbonyl)(2-((tert-butyldimethylsilyl)oxy)-2-(8-hydroxy-2-oxo-1,2-dihydroquinolin-5-yl)ethyl)amino)ethyl)benzyl)carbamoyl)thiophen-2-yl)boronic acid (166 mg, 87%). UPLC-MS Method 3; Rt 1.27 min, ES+ 721.68
  • 24
  • [ 779335-05-6 ]
  • C31H31N5O3S [ No CAS ]
  • 25
  • [ 779335-05-6 ]
  • C26H23N5OS*ClH [ No CAS ]
  • 26
  • [ 779335-05-6 ]
  • C29H25N5O2S [ No CAS ]
  • 27
  • [ 779335-05-6 ]
  • [ 3058-39-7 ]
  • 5-(4-cyanophenyl)thiophene-2-carboxylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; palladium diacetate; In 1,4-dioxane; water; at 100℃; To a degassed solution of Intermediate 74-a (500 mg, 1.9 mmol), intermediate 74-b (239 mg, 1.3 mmol) and potassium phosphate (557 mg, 2.6 mmol) in a 5: 1 mixture of 1 ,4- dioxane:water (5.0 ml) was added Pd(OAc)2 (15 mg, 0.06 mmol), S-Phos (54 mg, 0.1 mmol) and the reaction was heated at 100 C overnight and then cooled to room temperature. Water and ethyl acetate were added, the organic layer was separated. The aqueous phase was acidified to PH~1 , extracted twice with ethyl acetate, the combined organic extracts were washed with brine, dried over anhydrous MgSCU, filtered and concentrated under reduced pressure to provide Intermediate 74-c as a beige solid.
  • 28
  • [ 779335-05-6 ]
  • 3-(4-bromophenyl)-1-phenylimidazo[1,5-a]pyridine [ No CAS ]
  • 5-(4-(1-phenylimidazo[1,5-a]pyridin-3-yl)phenyl)thiophene-2-carboxylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
63% With bis-triphenylphosphine-palladium(II) chloride; potassium phosphate; In tetrahydrofuran; at 80℃;Inert atmosphere; A solution of 3-(4-bromophenyl)-1-phenylH-imidazo[1,5-a]pyridine(0.7 mmol), <strong>[779335-05-6]5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene-2-carboxylic acid</strong> (1.7 mmol) and K3PO4 (3.0 mmol) in anhydrous THF(20 mL) was thoroughly degassed by bubbling nitrogen for 15 min.Then, Pd(PPh3)Cl2 (10%) was added under nitrogen and the resultingsolution was degassed for further 5 min. The reaction mixture wasstirred at reflux (80 C) overnight. After cooling down, the reaction wasquenched with HCl 1M (5 mL) and the product was extracted withCH2Cl2 (3×30 mL). The combined organic phases were washed withbrine, dried over anhydrous Na2SO4 and the solvent was removed underreduced pressure. The crude product was purified by column chromatography(CH2Cl2/MeOH 92/8) to give the final product 6 as a darkyellow solid. Yield: 168 mg, 63%, MS (ESI): m/z 397.47 [(M + H)+],395.45 [(M-H)-]. 1H NMR (400 MHz, DMSO): delta=8.55 (d,J=7.2 Hz, 1H), 8.02 (d, J=9.2 Hz, 1H), 7.94 (m, 4H), 7.83 (d,J=8.5 Hz, 2H), 7.47 (m, 3H), 7.29 (m, 2H), 6.99 (dd, 1H), 6.81 (t, J6.5 Hz, 1H) ppm.
  • 29
  • [ 779335-05-6 ]
  • (nosyl)ethyl-4-((3-azidopropyl)carbamoyl)-2-iodobenzoic amide [ No CAS ]
  • C24H23N7O8S2 [ No CAS ]
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