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Chemical Structure| 874219-50-8 Chemical Structure| 874219-50-8

Structure of 874219-50-8

Chemical Structure| 874219-50-8

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Product Details of [ 874219-50-8 ]

CAS No. :874219-50-8
Formula : C10H14BNO3
M.W : 207.03
SMILES Code : C(C(C)C)(=O)NC1=CC=C(C=C1)B(O)O
MDL No. :MFCD08235068
InChI Key :DBWRRIVRDITVFV-UHFFFAOYSA-N
Pubchem ID :44119813

Safety of [ 874219-50-8 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P210-P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P332+P313-P337+P313-P362-P370+P378-P403+P233-P403+P235-P405-P501

Application In Synthesis of [ 874219-50-8 ]

* 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 [ 874219-50-8 ]

[ 874219-50-8 ] Synthesis Path-Downstream   1~5

  • 1
  • [ 874219-50-8 ]
  • [ 917757-98-3 ]
  • [ 1036386-39-6 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; at 100℃; for 0.166667h;Microwave irradiation; Then a mixture of 6-chloro-4-(2-methoxy-ethoxy)-pyrido[3,2-cf]pyrimidin-2-ylamine (15 mg), potassium carbonate (16 mg), tetrakis(triphenylphosphine) palladium (10 mg) and the corresponding boronic acid or pinacol ester (0.08 mmole) in DME (1 ml.) and water (0.5 ml_) was heated at 100C for 10 minutes by microwave. Solvents were concentrated in vacuo and the residue was purified by RP HPLC, using a C18 column with a gradient of H2O, 0.1% TFA-acetonitrile, to provide the desired product. This procedure provided, with yields ranging from 30% to 70% depending upon the aryl group introduced at the 6-position of the pyrido[3,2-c/]pyrimidine ring, the following pure compounds which were characterized by their mass spectrum MS as indicated in the following table 10.Table 10
  • 2
  • [ 874219-50-8 ]
  • [ 1036386-61-4 ]
  • [ 1036385-84-8 ]
YieldReaction ConditionsOperation in experiment
23% With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; at 100℃; for 0.166667h;Microwave irradiation; Then a mixture of 6-chloro-4-(2-fluoro-ethoxy)-pyrido[3,2-cdpyrimidin-2-ylamine (15 mg), potassium carbonate (16 mg), tetrakis(triphenylphosphine) palladium (10 mg) and <strong>[874219-50-8]4-isobutyramidophenylboronic acid</strong> (0.08 mmol) in DME (2 mL) and water (1 mL) was heated to 100C for 10 minutes by microwave. Solvents were concentrated in vacuo and the residue was purified by RP HPLC a C18 column with a gradient of H2O, 0.1% TFA-acetonitrile, to provide the desired product (4.4 mg, yield: 23%) which was characterized by its mass spectrum as follows: MS (m/z) 370 [M+H]+.
  • 3
  • [ 874219-50-8 ]
  • [(2R,3R,4R,5R,6R)-3-acetoxy-5-hydroxy-6-(3-hydroxy-4-methoxyphenyl)-4-[(2R,3S,4S,5R,6R)-3,4,5-triacetoxy-6-(acetoxymethyl)tetrahydropyran-2-yl]oxytetrahydropyran-2-yl]methyl acetate [ No CAS ]
  • [(2R,3R,4R,5R,6R)-3-acetoxy-5-hydroxy-6-[4-methoxy-3-[4-(2-methylpropanoylamino)phenoxy]phenyl]-4-[(2R,3S,4S,5R,6R)-3,4,5-triacetoxy-6-(acetoxymethyl)tetrahydropyran-2-yl]oxytetrahydropyran-2-yl]methyl acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
63.5 mg With 2,6-dimethylpyridine; copper diacetate; In dichloromethane; at 20℃; for 20.0h;Molecular sieve; To a solution of [(2R,3R,4R,5R,6R)-3-acetoxy-5-hydroxy-6-(3-hydroxy-4-methoxy- phenyl)-4-[(2R,3S,4S,5R,6R)-3,4,5-triacetoxy-6-(acetoxymethyl)tetrahydropyran-2-yl]oxy- tetrahydropyran-2-yl]methyl acetate (COMPOUND 289, Step II) (70 mg, 0.10 mmol) and [4-(2-methylpropanoylamino)phenyl]boronic acid (41.37 mg, 0.20 mmol) in DCM (5 mL) are added 4A molecular sieves powder (400 mg) and Cu(OAc)2 (25.41 mg, 0.1399 mmol). After stirring for 10 min, 2,6-lutidine (53.53 mg, 57.9 μ,, 0.50 mmol) is added to the mixture and stirred at rt for 20 h. The reaction mixture is filtered off to remove the molecular sieves, and concentrated to dryness. The residue is purified on Biotage SNAP 10 g silica gel cartridge using MeOH/DCM (0 to 7% in 20 CV) to provide an inseparable mixture containing expected compound (63.5mg).
  • 4
  • [ 874219-50-8 ]
  • [ 1533423-93-6 ]
  • N-[4'-(5-amino-1H-[1,2,4]triazol-3-ylamino)-2',6'-dichlorobiphenyl-4-yl]isobutyramide [ No CAS ]
YieldReaction ConditionsOperation in experiment
28% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate; In water; butan-1-ol; at 135℃; for 0.5h;Inert atmosphere; Microwave irradiation; To a 1 5 ni L microwave vial was added N3-(4-bromo-3,5-dichlorophenyl)-lH-l ,2,4-triazole-3,5- diamine Intermediate 2 (201 mg, 622 μηιο, Eq: 1 .00 ), <strong>[874219-50-8]4-isobutyramidophenylboronic acid</strong> (155 mg, 747 μπιοΙ, Eq: 1.2) and Cs2C03(608 mg, 1.87 mmol, Eq: 3) in n-BiiOH (3.00 ml ) and Water (600 μ). PdCl2(DPPF) (50.8 mg, 62.2 iimol. Eq: 0. 1 ) was added, the mixture was purged with argon, the vial was capped and heated in the microwave at 135C for 30 min. Diluted with dichloromethane, added Na2S04and filtered through cel ite. The filtrate was taken up in MeOH, filtered and concentrated. The crude material was purified by preparative HPLC (0.1%TFA in water/0.1% TFA in AcCN ) 95% to 10% TFA water over 25mins. Dried under vacuum overnight to afford 71 mg (28%) of the desired product as an off white solid.MS +m/z: 405.0/407.0. (M+l)
  • 5
  • [ 874219-50-8 ]
  • [ 1610679-56-5 ]
  • N-(4-(4-((4-methoxybenzyl)((tetrahydro-2H-pyran-4-yl)methyl)amino)-2-(methylthio)pyrazolo[1,5-a][1,3,5]triazin-8-yl)phenyl)isobutyramide [ No CAS ]
YieldReaction ConditionsOperation in experiment
67% With potassium phosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In tetrahydrofuran; water; at 100 - 130℃;Microwave irradiation; Inert atmosphere; General procedure: A mixture of8-bromo-N-(4-methoxybenzyl)-2-(methylthio)pyrazolo[1,5-a][1,3,5]triazin-4-amine (1.0 equiv) in THF (0.1 -0.5 M), aryl boronic acid or aryl boronate ester(1.1 - 1.5 equiv ), aq K3PO4(1 - 2 M, 3 -5 equiv) and PdCl2dppf.DCM (0.05 -0.1 equiv) was heated under Ar in a microwave reactor, an oil bath or a reaction block at temperatures 100-130 C . The product was partitioned between EtOAc and H2O , dried over Na2SO4or MgSO4, filtered, concentrated to dryness, and purified by flash chromatography. Alternatively, a trituration of crude product with MeOH provided the title compound with the required purity.
 

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