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Chemical Structure| 363186-06-5

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Product Details of [ 363186-06-5 ]

CAS No. :363186-06-5
Formula : C20H24BNO4
M.W : 353.22
SMILES Code : O=C(OCC1=CC=CC=C1)NC2=CC=C(B3OC(C)(C)C(C)(C)O3)C=C2
MDL No. :MFCD02179440
InChI Key :INBLGLWXMBCHFV-UHFFFAOYSA-N
Pubchem ID :4600564

Safety of [ 363186-06-5 ]

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

Application In Synthesis of [ 363186-06-5 ]

* 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 [ 363186-06-5 ]

[ 363186-06-5 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 363186-06-5 ]
  • [ 330793-48-1 ]
  • [ 461698-46-4 ]
YieldReaction ConditionsOperation in experiment
With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; diethyl ether; water; A. Tert-butyl 4-[4-amino-3-(4-[(benzyloxy)carbonyl]aminophenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-1-piperidinecarboxylate A mixture of <strong>[363186-06-5]benzyl N-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]carbamate</strong> (9.54 g, 0.027 mol), tert-butyl 4-(4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-1-piperidinecarboxylate (10.0 g, 0.0225 mol), tetrakis(triphenylphosphine)palladium (1.56 g, 0.00135 mol) and sodium carbonate (5.97 g, 0.0563 mol) was heated in a mixture of ethylene glycol dimethyl ether (120 mL) and water (60 mL) at 80 C. for 16 hours under an atmosphere of nitrogen. The mixture was allowed to cool to ambient temperature and solvents were removed under the reduced pressure. The residue was partitioned between water (150 mL) and dichloromethane (150 mL); the organic phase was washed with brine, dried with magnesium sulfate and concentrated under reduced pressure. The residue was triturated in diethyl ether and the precipitate was collected by filtration and dried to yield tert-butyl 4-[4-amino-3-(4-[(benzyloxy)carbonyl]aminophenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-1-piperidinecarboxylate (10.1 g, 0.0186 mol) as a white solid. 1H NMR (DMSO-d6, 400 MHz) δ 10.00 (s, 1H), 8.23 (s, 1H), 7.64 (d, 2H), 7.43 (d, 2H), 7.36 (m, 5H), 5.18 (s, 2H), 4.90 (m, 1H), 4.08 (br, 2H), 3.00 (br, 2H), 2.02 (m, 4H), 1.42 (s, 9H);
With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; diethyl ether; water; A. tert-butyl 4-[4-amino-3-(4-[(benzyloxy)carbonyl]aminophenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-1-piperidinecarboxylate A mixture of <strong>[363186-06-5]benzyl N-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]carbamate</strong> (9.54 g, 0.027 mol), tert-butyl 4-(4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-1-piperidinecarboxylate (10.0 g, 0.0225 mol), tetrakis(triphenylphosphine)palladium (1.56 g, 0.00135 mol) and sodium carbonate (5.97 g, 0.0563 mol) was heated in a mixture of ethylene glycol dimethyl ether (120 mL) and water (60 mL) at 80 C. for 16 hours under an atmosphere of nitrogen. The mixture was allowed to cool to ambient temperature and solvents were removed under the reduced pressure. The residue was partitioned between water (150 mL) and dichloromethane (150 mL); the organic phase was washed with brine, dried with magnesium sulfate and concentrated under reduced pressure. The residue was triturated in diethyl ether and the precipitate was collected by filtration and dried to yield tert-butyl 4-[4-amino-3-(4-[(benzyloxy)carbonyl]aminophenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-1-piperidinecarboxylate (10.1 g, 0.0186 mol) as a white solid. 1H NMR (DMSO-d6, 400 MHz) δ 10.00 (s, 1H), 8.23 (s, 1H), 7.64 (d, 2H), 7.43 (d, 2H), 7.36 (m, 5H), 5.18 (s, 2H), 4.90 (m, 1H), 4.08 (br, 2H), 3.00 (br, 2H), 2.02 (m, 4H), 1.42 (s, 9H);
With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; at 80.0℃; for 16.0h; [0752] A mixture of <strong>[363186-06-5]benzyl N-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]carbamate</strong> (9.54 g, 0.027 mol), tert-butyl 4-(4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-1-piperidinecarboxylate (10.0 g, 0.0225 mol), tetrakis-(triphenylphosphine)palladium (1.56 g, 0.00135 mol) and sodium carbonate (5.97 g, 0.0563 mol) was heated in a mixture of ethylene glycol dimethyl ether (120 mL) and water (60 mL) at 80 C. for 16 hours under an atmosphere of nitrogen. The mixture was allowed to cool to ambient temperature and solvents were removed under the reduced pressure. The residue was partitioned between water (150 mL) and dichloromethane (150 mL); the organic phase was washed with brine, dried with magnesium sulfate and concentrated under reduced pressure. The residue was triturated in diethyl ether and the precipitate was collected by filtration and dried to yield tert-butyl 4-[4-amino-3-(4-[(benzyloxy)carbonyl]aminophenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-1-piperidinecarboxylate (10.1 g, 0.0186 mol) as a white solid. [0753] 1H NMR (DMSO-d6, 400 MHz) δ 10.00 (s, 1H), 8.23 (s, 1H), 7.64 (d, 2H), 7.43 (d, 2H), 7.36 (m, 5H), 5.18 (s, 2H), 4.90 (m, 1H), 4.08 (br, 2H), 3.00 (br, 2H), 2.02 (m, 4H), 1.42 (s, 9H); [0754] RP-HPLC (Delta Pak C18, 5 μm, 300A, 15 cm; 5%-85% acetonitrile-0.1M ammonium acetate over 20 min, 1 mL/min) Rt 18.58 min.
  • 2
  • [ 93298-14-7 ]
  • [ 25015-63-8 ]
  • [ 363186-06-5 ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In 1,4-dioxane; water; ethyl acetate; REFERENCE EXAMPLE 133 [4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]carbamic acid phenylmethyl ester To a solution of (4-iodophenyl)carbamic acid phenylmethyl ester (6.50 g, 18.4 mmol) and triethylamine (7.7 mL, 55 mmol) in 1,4-dioxane (35 mL), [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) dichloromethane complex (150 mg, 0.184 mmol) was added, and 4,4,5,5-tetramethyl-1,3,2-dioxaborolane (5.9 mL, 41 mmol) was added dropwise. The resultant mixture was stirred at 85 C for 2.5 hours under nitrogen atmosphere. The reaction mixture was cooled with ice, combined with water, and extracted twice with ethyl acetate. The combined organic layer was washed with water and brine, dried through sodium sulfate-silica gel (eluding with ethyl acetate), and concentrated under reduced pressure. The residue was subjected to a column chromatography on a silica gel (hexane/ethyl acetate, 10:1 followed by 4:1) to obtain the title compound (5.47 g, yield: 84%). An oil. 1H NMR (CDCl3) δ 1.33 (12H, s), 5.20 (2H, s), 6.76 (1H, br s), 7.25-7.52 (7H, m), 7.75 (2H, d, J = 8.4 Hz).
  • 3
  • [ 363186-06-5 ]
  • [ 362715-87-5 ]
  • [3'-(3,4,8,9-tetrahydro-6-hydroxy-4,4,8,8-tetramethylfuro[2,3-h]isoquinolin-1-yl)[1,1'-biphenyl]-4-yl]carbamic acid phenylmethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium carbonate;tetrakis(triphenylphosphine)palladium (0); In 1,2-dimethoxyethane; ethanol; water; ethyl acetate; [3'-(3,4,8,9-Tetrahydro-6-hydroxy-4,4,8,8-tetramethylfuro[2,3-h]isoquinolin-1-yl)[1,1'-biphenyl]-4-yl]carbamic acid phenylmethyl ester A suspension of 1-(3-bromophenyl)-3,4,8,9-tetrahydro-4,4,8,8-tetramethyl-6-furo[2,3-h]isoquinolinol (2.40 g, 6.00 mmol), <strong>[363186-06-5][4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]carbamic acid phenylmethyl ester</strong> (2.54 g, 7.19 mmol), sodium carbonate (1.59 g, 15.0 mmol) and tetrakis(triphenylphosphine)palladium(0) (139 mg, 0.120 mmol) in 1.2-dimethoxyethane (20 mL), ethanol (10 mL) and water (10 mL) was stirred at 85 C for 16 hours under nitrogen atmosphere. The reaction mixture was combined with ethyl acetate and water, and the organic layer was separated, and the aqueous layer was extracted with ethyl acetate. The combined organic layer was washed with brine, dried through sodium sulfate-silica gel (eluding with ethyl acetate), and concentrated under reduced pressure. The residue was subjected to a column chromatography on a basic silica gel (hexane/ethyl acetate 1:2 followed by ethyl acetate), crystallized from ethyl acetate-chloroform to obtain the title compound (2.63 g, yield: 80%). Melting point: 161-165 C. 1H NMR (DMSO-d6) δ 1.15 (6H, s), 1.19 (6H, s), 2.25 (2H, s), 3.48 (2H, s), 5.17 (2H, s), 6.74 (1H, s), 7.31-7.75 (13H, m), 9.74 (1H, s), 9.91 (1H, s).
 

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