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Chemical Structure| 791852-35-2 Chemical Structure| 791852-35-2

Structure of 791852-35-2

Chemical Structure| 791852-35-2

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Product Details of [ 791852-35-2 ]

CAS No. :791852-35-2
Formula : C15H20ClN5O2
M.W : 337.81
SMILES Code : O=C(N1CCC(N2N=CC3=C(Cl)N=CN=C32)CC1)OC(C)(C)C
MDL No. :MFCD21606330

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Application In Synthesis of [ 791852-35-2 ]

* 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 [ 791852-35-2 ]

[ 791852-35-2 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 791852-35-2 ]
  • [ 13589-72-5 ]
  • [ 1196485-17-2 ]
YieldReaction ConditionsOperation in experiment
24% With potassium carbonate; In N,N-dimethyl-formamide; at 160℃; for 0.166667h;Microwave irradiation; Example 514-[4-(4-Chloro-2-cyano-phenoxy)-pyrazolo[3,4-d]pyrimidin-1-yl]-piperidine-1-carboxylic acid tert-butyl ester; A mixture of 4-(4-chloro-pyrazolo[3,4-d]pyrimidin-1-yl)-piperidine-1-carboxylic acid tert-butyl ester (Intermediate 19; 60 mg, 0.178 mmol), <strong>[13589-72-5]5-chloro-2-hydroxybenzonitrile</strong> (Maybridge, Tintagel, Cornwall, UK; 28 mg, 0.178 mmol), and potassium carbonate (54 mg, 0.392 mmol) in dimethylformamide (1 mL) was heated in the microwave oven at 160 C. for 10 min. Saturated sodium carbonate solution was added to the reaction mixture and the resulting precipitate was filtered through a silica gel plug, eluting with methanol. The solvent was removed and the residue was purified by HPLC to give 4-[4-(4-chloro-2-cyano-phenoxy)-pyrazolo[3,4-d]pyrimidin-1-yl]-piperidine-1-carboxylic acid tert-butyl ester (19 mg, 24%) as a white solid. Mass spectrum MH+=455. 1H NMR (300 MHz, DMSO-d6) delta 1.41 (s, 9H), 1.96-2.04 (m, 4H), 2.96-3.08 (m, 2H), 4.02-4.12 (m, 2H), 4.96-5.06 (m, 1H), 7.69 (d, 1H, J=8.7 Hz), 7.94 (dd, 1H, J=2.6, 8.9 Hz), 8.25 (d, 1H, J=2.4 Hz), 8.50 (s, 1H), 8.57 (s, 1H).
  • 2
  • [ 791852-35-2 ]
  • [ 403-01-0 ]
  • [ 1196485-32-1 ]
YieldReaction ConditionsOperation in experiment
37% With potassium carbonate; In N,N-dimethyl-formamide; at 160℃; for 0.166667h;Microwave irradiation; Example 634-[4-(2-Fluoro-4-methoxycarbonyl-phenoxy)-pyrazolo[3,4-d]pyrimidin-1-yl]-piperidine-1-carboxylic acid tert-butyl ester; A mixture of <strong>[403-01-0]3-fluoro-4-hydroxy-benzoic acid methyl ester</strong> (Combi-Blocks Inc, San Diego, Calif., USA; 31 mg, 0.178 mmol), 4-(4-chloro-pyrazolo[3,4-d]pyrimidin-1-yl)-piperidine-1-carboxylic acid tert-butyl ester (Intermediate 19; 60 mg, 0.178 mmol), and potassium carbonate (54 mg, 0.391 mmol) in dimethylformamide (1 mL) was heated in a microwave oven at 160° C. for 10 min. Saturated sodium carbonate solution was added to the reaction mixture, and the mixture was then filtered through a pad of silica gel to remove the precipitate. The silica gel pad was washed with methanol and the solvents were evaporated from the filtrate. The residue was purified by HPLC to afford 4-[4-(2-fluoro-4-methoxycarbonyl-phenoxy)-pyrazolo[3,4-d]pyrimidin-1-yl]-piperidine-1-carboxylic acid tert-butyl ester (31 mg, 37percent) as a white solid. Mass spectrum MH+=472.
  • 3
  • [ 791852-35-2 ]
  • [ 387350-92-7 ]
  • [ 1196484-67-9 ]
YieldReaction ConditionsOperation in experiment
21% With caesium carbonate; In N,N-dimethyl-formamide; at 70℃; Example 104-[4-(5-Methanesulfonyl-2,3-dihydro-indol-1-yl)-pyrazolo[3,4-d]pyrimidin-1-yl]-piperidine-1-carboxylic acid tert-butyl ester; 5-(Methylsulfonyl)-indoline (Matrix Scientific, Columbia, S.C., USA; 30 mg, 0.15 mmol) and triethylamine (70 μL, 0.5 mmol) were added to a solution of 4-(4-chloro-pyrazolo[3,4-d]pyrimidin-1-yl)-piperidine-1-carboxylic acid tert-butyl ester (Intermediate 19; 45 mg, 0.133 mmol) in tetrahydrofuran (1 mL). The mixture was heated to reflux. No reaction had occurred after 2 h. The volatiles were evaporated. Dimethylformamide (1 mL) and cesium carbonate (250 mg, 0.77 mmol) were added. The mixture was heated at 70 C. overnight, then poured into saturated aqueous sodium bicarbonate, and extracted three times with ethyl acetate. The combined organic extracts were washed twice with water and once with brine, dried (magnesium sulfate), filtered, evaporated, and purified by column chromatography eluting with ethyl acetate to give 4-[4-(5-methanesulfonyl-2,3-dihydro-indol-1-yl)pyrazolo[3,4-d]pyrimidin-1-yl]-piperidine-1-carboxylic acid tert-butyl ester (14 mg, 21%) as an off-white solid.
  • 4
  • [ 791852-35-2 ]
  • [ 897732-75-1 ]
  • [ 1196484-63-5 ]
YieldReaction ConditionsOperation in experiment
46% With sodium t-butanolate;palladium diacetate; 2,8,9-tris(2-methylpropyl)-2,5,8,9-tetraaza-1-phosphabicyclo[3.3.3]undecane; In N,N-dimethyl-formamide; at 160℃; for 0.166667h;Microwave irradiation; Example 84-[4-(6-Methanesulfonyl-2-methyl-pyridin-3-ylamino)-pyrazolo[3,4-d]pyrimidin-1-yl]-piperidine-1-carboxylic acid tert-butyl ester; A mixture of 4-(4-chloro-pyrazolo[3,4-d]pyrimidin-1-yl)-piperidine-1-carboxylic acid tert-butyl ester (Intermediate 19; 50 mg, 0.15 mmol), <strong>[897732-75-1]6-methanesulfonyl-2-methyl-pyridin-3-ylamine</strong> (Intermediate 4; 28 mg, 0.15 mmol), palladium acetate (0.33 mg, 0.01 equivalent), sodium tert-butoxide (34 mg, 0.36 mmol), and 2,8,9-triisobutyl-2,5,8,9-tetraaza-1-phosphabicyclo[3.3.3]undecane (Aldrich, 1 mg, 0.02 equivalents) in dimethylformamide (2 mL) was heated in the microwave oven at 160 C. for 10 min. Ethyl acetate and water were added, and the aqueous layer was extracted three times with ethyl acetate. The ethyl acetate layers were combined, evaporated, and purified by preparative C18 HPLC, eluting with 10-100% acetonitrile/water. Samples containing the product were extracted twice with dichloromethane and the solvent was evaporated under high vacuum to give 4-[4-(6-methanesulfonyl-2-methyl-pyridin-3-ylamino)-pyrazolo[3,4-d]pyrimidin-1-yl]-piperidine-1-carboxylic acid tert-butyl ester (34 mg, 46%) as a white powder. 1H NMR (300 MHz, DMSO-d6) delta 1.41 (s, 9H), 1.92-2.00 (m, 4H), 2.55 (s, 3H), 2.90-3.04 (m, 2H), 3.30 (water peak and SO2CH3 peak), 4.00-4.12 (m, 2H), 4.84-4.96 (m, 1H), 7.92 (d, 1H, J=8.5 Hz), 8.22-8.36 (m, 3H), 10.06 (br s, 1H). HRMS Calcd. for C22H30N7O4S (MH+): 488.2075. Found: 488.2073.
 

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