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[ CAS No. 885325-91-7 ]

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2D
Chemical Structure| 885325-91-7
Chemical Structure| 885325-91-7
Structure of 885325-91-7 *Storage: {[proInfo.prStorage]}

Quality Control of [ 885325-91-7 ]

Purity: {[proInfo.showProBatch.pb_purity]}

Related Doc. of [ 885325-91-7 ]

SDS

Product Details of [ 885325-91-7 ]

CAS No. :885325-91-7MDL No. :MFCD24623294
Formula :C9H19N3OSiBoiling Point :-
Linear Structure Formula :-InChI Key :N/A
M.W :213.35Pubchem ID :57562604
Synonyms :

Computed Properties of [ 885325-91-7 ]

TPSA : - H-Bond Acceptor Count : -
XLogP3 : - H-Bond Donor Count : -
SP3 : - Rotatable Bond Count : -

Safety of [ 885325-91-7 ]

Signal Word:WarningClassN/A
Precautionary Statements:P261-P305 P351 P338UN#:N/A
Hazard Statements:H302-H315-H319-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 885325-91-7 ]

  • Downstream synthetic route of [ 885325-91-7 ]

[ 885325-91-7 ] Synthesis Path-Downstream   1~10

  • 1
  • [ 885325-91-7 ]
  • N-(tert-butyl)-2-(3-(5-(2,2-difluoroethoxy)-6-methyl-4-oxo-3,4-dihydroquinazolin-2-yl)phenoxy)acetamide [ No CAS ]
  • [ 76-05-1 ]
  • 2-(3-(4-((1H-pyrazol-3-yl)amino)-5-(2,2-difluoroethoxy)-6-methylquinazolin-2-yl)phenoxy)-N-(tert-butyl)acetamide bis trifluoroacetic acid salt [ No CAS ]
YieldReaction ConditionsOperation in experiment
5% An 8 mL vial equipped with a Teflon septum and magnetic stir bar was charged with N-(tert-butyl)-2-(3-(5-(2,2-difluoroethoxy)-6-methyl-4-oxo-3,4-dihydroquinazolin-2-yl)- phenoxy)acetamide (59 mg, 132 mmol) and BOP (88 mg, 199 mmol) followed by dry NMP (0.66 mL) and DBU (50 mL, 331 mmol). The reaction mixture was stirred at room temperature for 60 minutes after which, LC-MS showed complete conversion to Bt-activated substrate ([M+H]+ = 563). The reaction mixture was diluted with 10 mL of 1:1 hexane/EtOAc and passed through a 12 g silica-cartridge using the same eluent. The collected solution was evaporated under reduced pressure and the purified Bt-activated substrate was dissolved in dry DMA (331 mL) before [885325-91-7]1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-3-amine (57 mg, 265 mmol) and DIPEA (58 mL, 331 mmol) were added. Stirring was continued for 12 h at 90 C, after which LC-MS showed no Bt activated substrate left and a large UV peak with the desired m/z. The reaction mixture was cooled down to room temperature, evaporated to dryness under reduced pressure and subjected to flash column chromatography (0% to 90% EtOAc in hexane). The desired fractions were collected and the residue from evaporation was dissolved in 6 mL of DCE followed by 4 mL of TFA. After 12 h, LCMS indicated that complete SEM deprotection had occurred. Volatiles were removed under reduced pressure and the crude residue was purified by HPLC to afford 2-(3-(4-((1H-pyrazol-3-yl)amino)-5- (2,2-difluoroethoxy)-6-methylquinazolin-2-yl)phenoxy)-N-(tert-butyl)acetamide bis trifluoroacetic acid salt (4 mg, 5%) as a bright yellow powder. MS (ES+) m/e 511 (M+H)+.
  • 2
  • [ 885325-91-7 ]
  • N-(tert-butyl)-2-(3-(5-ethoxy-4-hydroxyquinazolin-2-yl)phenoxy)acetamide [ No CAS ]
  • N-(tert-butyl)-2-(3-(5-ethoxy-4-((1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-3-yl)amino)quinazolin-2-yl)phenoxy)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
To a mixture of N-(tert-butyl)-2-(3-(5-ethoxy-4-hydroxyquinazolin-2-yl)- phenoxy)acetamide (200 mg, 505.75 mumol), BOP (335.53 mg, 758.63 mumol) in MeCN (4 mL) was added DIPEA (130.73 mg, 1.01 mmol, 176.19 muL). The mixture was stirred at 20 C for 16 h. The mixture was concentrated under reduced pressure to give a residue. The residue was dissolved into NMP (4 mL), [885325-91-7]1-(2-trimethylsilylethoxymethyl)pyrazol-3-amine (215.81 mg, crude) was added. The mixture was stirred at 80 C for 16 h. The reaction mixture was cooled to room temperature, quenched by H2O (100 mL) and extracted with EtOAc (100 mL×3). The combined organic layers were washed by brine (100 mL), dried over Na2SO4, concentrated under reduced pressure to give a residue. The residue was purified by prep-TLC (SiO2, Petroleum ether/Ethyl acetate=0/1) to provide the title compound (300 mg, 56%, 56% purity) as a yellow oil.
  • 3
  • [ 885325-91-7 ]
  • 2,4-dichloro-6-propoxyquinazoline [ No CAS ]
  • 2-chloro-6-propoxy-N-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-3-yl)quinazolin-4-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
330 mg With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 25 - 60℃; for 15h; To a solution of 2,4-dichloro-6-propoxyquinazoline (500 mg, 1.94 mmol) and [885325-91-7]1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-3-amine (414.89 mg, crude) in DMF (7 mL) was added DIEA (502.67 mg, 3.89 mmol, 677.45 muL) at 25C, and then the reaction mixture was heated to 60C and stirred for 15 hours. The reaction mixture was cooled to room temperature and poured into H2O (60 mL) and the aqueous layer was extracted with EtOAc (20 mL×3). The combined organic phases were washed with brine (30 mL), dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography (SiO2, Petroleum ether/Ethyl acetate=10/1) to provide the title compound (330 mg, 39%) as a light yellow solid. 1H NMR (400 MHz, DMSO-d6) d 8.29 (s, 1H), 7.76 (d, J = 9.2 Hz, 1H), 7.56 (d, J = 2.4 Hz, 1H), 7.43 (dd, J = 2.4, 9.2 Hz, 1H), 7.23 (d, J = 2.4 Hz, 1H), 7.07 (d, J = 2.4 Hz, 1H), 5.35 (s, 2H), 3.99 (t, J = 6.4 Hz, 2H), 3.60-3.53 (m, 2H), 1.94-1.83 (m, 2H), 1.09 (t, J = 7.6 Hz, 3H), 0.97-0.89 (m, 2H), 0.01 (s, 9H).
  • 4
  • [ 885325-91-7 ]
  • 2,4-dichloro-6-isopropoxyquinazoline [ No CAS ]
  • 2-chloro-6-isopropoxy-N-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-3-yl)quinazolin-4-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 60℃; for 16h; To a mixture of 2,4-dichloro-6-isopropoxyquinazoline (500 mg, 1.94 mmol) and [885325-91-7]1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-3-amine (414.89 mg) in DMF (5 mL) was added DIPEA (502.67 mg, 3.89 mmol, 677.45 muL). The mixture was stirred at 60 C for 16 h. The reaction mixture was cooled to room temperature and diluted with water (20 mL). The resulting mixture was extracted with EtOAc (20 mL×3). The combined organic layers were washed with brine (20 mL×2), dried overNa2SO4, filtered and concentrated under reduced pressure to give a residue. The residue was purified by column chromatography (SiO2, Petroleum ether/Ethyl acetate = 80/1 to 10:1, Rf = 0.1) to provide the title compound (460 mg, crude) as a yellow solid.
  • 5
  • [ 885325-91-7 ]
  • N-(tert-butyl)-2-(3-(6-propoxy-4-((1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-3-yl)amino)quinazolin-2-yl)phenoxy)acetamide [ No CAS ]
  • 6
  • [ 885325-91-7 ]
  • N-(tert-butyl)-2-(3-(6-isopropoxy-4-((1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-3-yl)amino)quinazolin-2-yl)phenoxy)acetamide [ No CAS ]
  • 7
  • [ 885325-91-7 ]
  • (rac)-trans-3-amino-4-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propyl)-1-(N-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-3-yl)sulfamoyl)pyrrolidine-3-carboxylic acid [ No CAS ]
  • 8
  • [ 885325-91-7 ]
  • (rac)-benzyl trans-3-azido-4-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propyl)-1-(N-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-3-yl)sulfamoyl)pyrrolidine-3-carboxylate [ No CAS ]
  • 9
  • [ 885325-91-7 ]
  • (rac)-benzyl trans-4-allyl-3-azido-1-(N-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-3-yl)sulfamoyl)pyrrolidine-3-carboxylate [ No CAS ]
  • 10
  • [ 1189-71-5 ]
  • [ 885325-91-7 ]
  • [ 540-51-2 ]
  • 2-oxo-N-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-3-yl)oxazolidine-3-sulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
24% In a glass vial-1, to a solution of sulfurisocyanatidic chloride (0.829 g, 5.858 mmol) in DCM (10 mL) was added 2-bromoethan-1-ol (0.732 g, 5.858 mmol) at 0C and stirred for 1h. Simultaneously in glass vial-2, to a solution of the product of step 2 (1.5 g, 7.03 mmol) in DCM (10 mL) was added TEA (1.186 g, 11.716 mmol) at 0 C and stirred for 1 h. After 1 h, the reaction mixture of vial-2 was added to the reaction mixture in vial-1 at 0 C. The resulting reaction mixture was stirred at r.t. for 2 h. The resulting reaction mixture was poured into water (25 mL) and extracted with DCM (2 X 25 mL). The combined organic phased was dried over anhydrous Na2SO4 and concentrated and purified by silica gel flash chromatography (MeOH: DCM=0 to 10%) to give 0.6 g of the title compound. Yield: 24%. MS (ESI, m/e) : 363 [M+1] +.
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