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[ CAS No. 269409-71-4 ]

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Chemical Structure| 269409-71-4
Chemical Structure| 269409-71-4
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Product Details of [ 269409-71-4 ]

CAS No. :269409-71-4 MDL No. :MFCD22414462
Formula : C14H19BO5 Boiling Point : -
Linear Structure Formula :- InChI Key :N/A
M.W :278.11 g/mol Pubchem ID :-
Synonyms :

Safety of [ 269409-71-4 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P330-P363-P501 UN#:
Hazard Statements:H302-H312-H332 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 269409-71-4 ]

  • Downstream synthetic route of [ 269409-71-4 ]

[ 269409-71-4 ] Synthesis Path-Downstream   1~5

  • 2
  • [ 68507-19-7 ]
  • [ 25015-63-8 ]
  • [ 269409-71-4 ]
YieldReaction ConditionsOperation in experiment
With triethylamine;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,4-dioxane; at 80℃; for 8h; [00164] To 26.9 mg PdCl2(dppf).CH2Cl2 in a reaction tube under nitrogen were added 4 ml dioxane, 0.43 ml (3 mmol) triethylamine, 0.35 ml (2.4 mmol) pinacolborane and 277 mg (1.0 mmol) <strong>[68507-19-7]3-iodo-4-methoxybenzoic acid</strong>. The reaction solution was stirred at room temp. to ensure that all the phenolic groups had reacted with pinacolborane and the hydrogen evolved was flushed out of the reaction tube with argon. The reaction solution was warmed to 80 C. with stirring in an oil bath for 8 h. An aliquot (0.3 ml) was removed from the reaction solution, extracted into ethyl acetate, washed with dilute sulphuric acid and then several times with water and analysed by gc (fid detector, SGE HT5 capillary column). There was only one peak in the gc at retention time longer than that for <strong>[68507-19-7]3-iodo-4-methoxybenzoic acid</strong> and that was confirmed by gc/ms to be due to the desired arylboronic acid pinacol ester.
  • 3
  • [ 269409-71-4 ]
  • tert-butyl ((1S,2R)-2-((6-bromoquinazolin-2-yl)amino)cyclopentyl)carbamate [ No CAS ]
  • 3-(2-(((1R,2S)-2-((tert-butoxycarbonyl)amino)cyclopentyl)amino)quinazolin-6-yl)-4-methoxybenzoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
96% With potassium phosphate; bis(di-tert-​butyl(4-​dimethylaminophenyl)​phosphine)​dichloropalladium(II) In 1,4-dioxane; water at 100℃; for 0.5h; Inert atmosphere; Microwave irradiation; 2 Step 2: Synthesis of 4-(2-((1R,2S)-2-((tert-butoxycarbonyl)amino)cyclopentyl)amino)quinazolin-6-yl)-3-methoxybenzoic acid A mixture of tert-butyl ((1S,2R)-2-((6-bromoquinazolin-2-yl)amino)cyclopentyl)carbamate (100 mg, 0.25 mmol), 3-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid (82 mg, 0.29 mmol), Bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) (9 mg, 0.01 mmol) and potassium phosphate (157 mg, 0.74 mmol) in 1,4-dioxane/ water (2.5 mL/0.25 mL) was degassed with nitrogen for 5 min and stirred at 100° C. for 30 min under microwave. The reaction mixture was cooled to room temperature, diluted with ethyl acetate, washed with saturated ammonium chloride solution and dried with sodium sulfate. The residue was purified by silica gel column chromatography to afford methyl 4-(2-(((1R,2S)-2-((tert-butoxycarbonyl)amino)cyclopentyl)amino)quinazolin-6-yl)-3-methoxybenzoic acid (114 mg, 96%). MS (ES+) C26H30N4O5 requires: 478, found: 479 [M+H]+.
  • 4
  • [ 269409-71-4 ]
  • 7-bromo-5-[1-(4-chlorophenyl)ethyl]-3-methyl[1,2]oxazolo[4,5-d]pyridazin-4(5H)-one [ No CAS ]
  • 3-{5-[1-(4-chlorophenyl)ethyl]-3-methyl-4-oxo-4,5-dihydro[1,2]oxazolo[4,5-d]pyridazin-7-yl}-4-methoxybenzoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
20% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; water; toluene at 130℃; for 0.5h; Inert atmosphere; Microwave irradiation; 73 3-{5-[1-(4-chlorophenyl)ethyl]-3-methyl-4-oxo-4,5-dihydro[1,2]oxazolo[4,5-d]pyridazin-7-yl}-4-methoxybenzoic acid Example 73 3-{5-[1-(4-chlorophenyl)ethyl]-3-methyl-4-oxo-4,5-dihydro[1,2]oxazolo[4,5-d]pyridazin-7-yl}-4-methoxybenzoic acid 7-Bromo-5-[1-(4-chlorophenyl)ethyl]-3-methyl[1,2]oxazolo[4,5-d]pyridazin-4(5H)-one (80 mg, 0.217 mmol, Example 39-Step 5) in ethanol/toluene (1:1, 2.4 mL) was combined with 2 M aqueous sodium carbonate (0.163 mL, 0.326 mmol) and 4-methoxy-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid (60.4 mg, 0.217 mmol). Then tetrakis(triphenylphosphine)palladium(0) (25.08 mg, 0.022 mmol) was added, and the mixture was heated in a Biotage microwave reactor for 30 minutes at 130° C. under an argon atmosphere. The reaction mixture was partitioned between water and ethyl acetate. The aqueous phase was extracted twice more with ethyl acetate. The combined organic fractions were then washed with brine, dried over MgSO4, and concentrated under reduced pressure. The residue was purified by flash chromatography on a Teledyne Isco CombiFlash apparatus using a silica gel cartridge (4 g) eluted with 10% methanol/dichloromethane. The residue was stirred in a small amount of diisopropyl ether, and the precipitate was collected to give the titled compound (19 mg, yield 20%). 1H NMR (600 MHz, DMSO-d6) δ ppm 12.94 (s, 1H), 8.13 (dd, J=8.7, 2.2 Hz, 1H), 8.03 (d, J=2.2 Hz, 1H), 7.41 (s, 4H), 6.33 (q, J=7.0 Hz, 1H), 3.87 (s, 3H), 2.59 (s, 3H), 1.74 (d, J=7.1 Hz, 3H); MS (ESI+) m/z 440.1 (M+H)+.
  • 5
  • [ 269409-71-4 ]
  • (1-(4-bromophenyl)-6-azaspiro[2.5]octan-6-yl)((R)-tetrahydrofuran-2-yl)methanone [ No CAS ]
  • 6-methoxy-4'-((S)-6-((R)-tetrahydrofuran-2-carbonyl)-6-azaspiro[2.5]octan-1-yl)-[1,1'-biphenyl]-3-carboxylic acid [ No CAS ]
  • 6-methoxy-4'-((R)-6-((R)-tetrahydrofuran-2-carbonyl)-6-azaspiro[2.5]octan-1-yl)-[1,1'-biphenyl]-3-carboxylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium phosphate; bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) In 1,4-dioxane; water at 90℃; for 2h; Inert atmosphere; 2.10.1 Method 10: Preparation of Compounds 68 and 69: 6-methoxy-4'-((S)-6-((R)-tetrahydrofuran-2-carbonyl)-6-azaspiro[2.5]octan-1-yl)-[1,1'-biphenyl]-3-carboxylic acid and 6-methoxy-4'-((R)-6-((R)-tetrahydrofuran-2-carbonyl)-6-azaspiro[2.5]octan-1-yl)-[1,1'-biphenyl]-3-carboxylic acid A mixture of (1-(4-bromophenyl)-6-azaspiro[2.5]octan-6-yl)((R)-tetrahydrofuran-2-yl)methanone (450 mg, 1.24 mmol), 4-methoxy-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid (409 mg, 1.48 mmol), bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium (87 mg,0.12 mmol) and potassium phosphate (770 mg, 3.52 mmol) in dioxane (15 mL) and water (3 mL) was stirred for 2 h at 90 °C under nitrogen atmosphere. The resulting mixture was cooled to room temperature and concentrated under reduced pressure. The residue was purified by reverse flash chromatography with water (containing 0.1% FA) and ACN (10% to 55% over 30 min). The product separated by Chiral HPLC with the following conditions: Column: CHIRALPAK IC, 2 × 25 cm, 5 µm; mobile phase: (Hexanes: DCM=3:1) (0.1% FA) and IPA (hold 50% IPA in 25 min); Detector: UV254 nm to afford the first eluting peak as Compound 68 (68.9 mg, 13%) and the second eluting peak as Compound 69 (95.7 mg, 17%) as a white solid. Compound 68: 1H-NMR(CD3OD, 400 MHz) (ppm): 8.09-7.99 (m, 1H), 7.99-7.89 (m, 1H), 7.45 (d, J=8.0 Hz, 2H), 7.35-7.22 (m, 2H), 7.16 (7.45 (d, J=8.8 Hz, 1H), 4.81-4.61 (m, 1H), 4.05-3.91 (m, 1H), 3.89 (s, 3H), 3.88-3.55 (m, 3H), 3.52-3.35 (m, 2H), 2.40-2.12 (m, 2H), 2.10-1.81 (m, 3H), 1.78-1.51 (m, 2H), 1.48-1.21 (m, 2H), 1.19-1.03 (m, 1H), 1.02-0.84 (m, 1H). LCMS (ES, m/z): 436 [M+H]+. Compound 69:1H-NMR(CD3OD, 400 MHz) (ppm): 8.01-7.91 (m, 1H), 7.90-7.65 (m, 1H), 7.42 (d, J=8.0 Hz, 2H), 7.29 (d, J=8.0 Hz, 2H), 7.20 (d, J=8.8 Hz, 1H), 4.78-4.51 (m, 1H), 3.85 (s, 3H), 3.84-3.67 (m, 2H), 3.65-3.51 (m, 2H), 3.28-3.09 (m, 2H), 2.19-2.05 (m, 1H), 2.04-1.88 (m, 2H), 1.87-1.68 (m, 2H), 1.61-1.40 (m, 2H), 1.30-1.00 (m, 3H), 0.99-0.79 (m, 1H). LCMS (ES, m/z): 436 [M+H]+.
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