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[ CAS No. 747412-49-3 ]

{[proInfo.proName]} (Synonyms:VER-52296; AUY-922; NVP-AUY 922) ,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
2D
Chemical Structure| 747412-49-3
Chemical Structure| 747412-49-3
Structure of 747412-49-3 *Storage: {[proInfo.prStorage]}

Quality Control of [ 747412-49-3 ]

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Alternatived Products of [ 747412-49-3 ]

Product Details of [ 747412-49-3 ]

CAS No. :747412-49-3MDL No. :MFCD14635361
Formula : C26H31N3O5 Boiling Point : 640.1°C at 760 mmHg
Linear Structure Formula :-InChI Key :N/A
M.W :465.54Pubchem ID :135539077
Synonyms :

1. Luminespib

Computed Properties of [ 747412-49-3 ]

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

Safety of [ 747412-49-3 ]

Signal Word:WarningClass:N/A
Precautionary Statements:P261-P305+P351+P338UN#:N/A
Hazard Statements:H302-H315-H319Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 747412-49-3 ]

  • Downstream synthetic route of [ 747412-49-3 ]

[ 747412-49-3 ] Synthesis Path-Downstream   1~6

  • 1
  • 5-(2,4-bis-benzyloxy-5-isopropyl-phenyl)-4-(4-morpholin-4-ylmethyl-phenyl)-isoxazole-3-carboxylic acid ethylamide [ No CAS ]
  • [ 747412-49-3 ]
YieldReaction ConditionsOperation in experiment
With boron trichloride; In dichloromethane; at 0℃; for 0.5h; 5- (2, 4-BIS-BENZYLOXY-5-ISOPROPYL-PHENYL)-4- (4-MORPHOLIN-4-YLMETHYL-PHENYL)- isoxazole-3-carboxylic acid ETHYLAMIDE (1EQ) was dissolved in an. DCM and under a nitrogen atmosphere, was cooled to 0 C. 1 MBCI3 in DCM was added drop wise and the solution was stirred under these conditions for 30 minutes. Methanol (2ML) was added and the reaction mixture was concentrated in vacuo. Purification of the sample by preparative LC/MS gave 5- (2, 4- DIHYDROXY-5-ISOPROPYL-PHENYL)-4- (4-MORPHOLIN-4-YLMETHYL-PHENYL)-ISOXAZOLE-3- carboxylic acid ethylamide as a white solid. LC retention time 1. 991 MIN [M+H] + 466.3 This compound had activity'A'in the HSP90 fluorescence polarization assay.
  • 2
  • [ 747412-49-3 ]
  • [ 75-75-2 ]
  • 5-(2,4-dihydroxy-5-isopropyl-phenyl)-4-(4-morpholin-4-ylmethyl-phenyl)-isoxazole-3-carboxylic acid ethylamide mesylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% In tert-butyl methyl ether; water; acetone; at 0 - 45℃; for 26 - 26.5833h;Product distribution / selectivity; Example 2: 5-(2,4-Dihvdroxv-5-isopropvl-phenvl)-4-(4-morpholin-4-vlmethyl-phenvl)- isoxazole-3-carboxylic acid ethylamide mesylate - Conditions (A)A stirred suspension of 5-(2,4-dihydroxy-5-isopropyl-phenyl)-4-(4-morpholin-4-ylmethyl- phenyl)-isoxazole-3-carboxylic acid ethylamide (7.76 g, 15 mmol, containing about 9 wtpercent TBME) in acetone (15 ml) is warmed to 35°C. To the mixture is added a solution of methanesulfonic acid (1.43 g, 14.85 mmol) in water (3.33 g) over 20 min. After 15 min, the solution is warmed to 45°C and clear filtered into a warm flask (about 45°C). The filter is rinsed with acetone/water 9:1 (v/v, 12 ml). The 45°C warm filtrate is diluted with acetone (53 ml) over 30 min and seeded with 5-(2,4-dihydroxy-5-isopropyl-phenyl)-4-(4-morpholin-4- ylmethyl-phenyl)-isoxazole-3-carboxylic acid ethylamide methanesulfonic acid salt (4 mg) whereupon crystallization begins. After 1 h at 45°C acetone (30 ml) is added. The suspension is stirred at 45°C for 1 h before it is cooled to 24°C over 90 min. TBME (20 ml) is added, and the suspension is stirred at about 24°C for 15 h. Two more portions of TBME (20 ml each) are added followed by 2 h stirring each time. Thereafter, the suspension is cooled to 0-50C and stirred for 3 h before it is filtered. The filter cake is washed with acetone/ tert- butyl methyl ether 3:1 (v/v) and dried under reduced pressure at 500C for about 17 h to give 7.18 g (85 percent) of the title compound as a white, crystalline powder. Melting point: 233°CWhen seeding is left out, the formed crystals are of the same form but may contain up to 1.5 wtpercent of acetone. Example 3: 5-(2,4-Dihydroxy-5-isopropyl-phenyl)-4-(4-morpholin-4-ylmethyl-phenyl)- isoxazole-3-carboxylic acid ethylamide mesylate - Conditions (B)186.2 mg (0.4 mmol) of 5-(2,4-Dihydroxy-5-isopropyl-phenyl)-4-(4-morpholin-4-ylmethyl- phenyl)-isoxazole-3-carboxylic acid ethylamide methane sulphonic acid are dissolved in 0.75 ml acetone. 154 mg of an aqueous solution (25 percent w/w) of methane sulphonic acid (0.4 mmol) are added at RT resulting in a blue solution. After stirring for 2 h, 3.5 ml acetone and <n="14"/>0.5 ml TBME are added. After the solution is stirred for further 12 h, further 3.5 ml of TBME is slowly added, and stirring is continued for further 12 h. The obtained emulsion is filtrated and the obtained solid washed with 0.5 ml TBME. The solid is dried for 16 h at 50 0C at 20 mbar to provide 180 mg of the title compound.
  • 3
  • [ 747412-49-3 ]
  • 5-(2,4-dihydroxy-5-isopropyl-phenyl)-4-(4-morpholin-4-ylmethyl-phenyl)-isoxazole-3-carboxylic acid ethylamide hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; In ethanol; water; ethyl acetate; at 25℃; Example 1 : 5-(2,4-Dihvdroxv-5-isopropvl-phenvl)-4-(4-morpholin-4-vlmethyl-phenvl)- isoxazole-3-carboxylic acid ethylamide hydrochloric acid salt5-(2,4-Dihydroxy-5-isopropyl-phenyl)-4-(4-morpholin-4-ylmethyl-phenyl)-isoxazole-3- carboxylic acid ethylamide (4.19 g, 9 mmol) is dissolved in absolute alcohol (19.7 ml) under gentle warming. After stirring for 5 min, 6N aqueous hydrochloric acid (1.5 ml, 9 mmol) is added at RT (about 25°C). The clear solution is seeded with a very small amount of 5-(2,4- dihydroxy-5-isopropyl-phenyl)-4-(4-morpholin-4-ylmethyl-phenyl)-isoxazole-3-carboxylic acid ethylamide hydrochloric acid salt and ethyl acetate (2 ml) is added whereupon the mixture becomes turbid slowly. After 1 h EtOAc (5 ml) is added in portions, and the suspension is stirred at RT overnight. More EtOAc (2 ml) is added. The suspension is stirred for about 5 h and filtered. The filter cake is washed with absolute alcohol/EtOAc 1 :1 (v/v) and dried for 16 h at 45°C under reduced pressure to result in the title compound as a white powder. Melting point (DSC): 237°C
  • 4
  • cholesteryl hemi-4-oxaglutarate [ No CAS ]
  • [ 747412-49-3 ]
  • AUY922-diglycolate-cholesterol [ No CAS ]
YieldReaction ConditionsOperation in experiment
24% With dmap; diisopropyl-carbodiimide; In dichloromethane; at 19℃; for 4.25h;Inert atmosphere; Step 2: Synthesis of AUY922-diglycolate-cholesterol: Weighed amounts of cholesterol-diglycolic acid (2, 12.0 g, 23.86 mmol), AUY922 (3, 10.0 g, 21.48 mmol) and N,N-dimethylamino pyridine (3.0 g, 24.55 mmol) were stored under high vacuum for 10 minutes and purged with nitrogen. The contents were then dissolved in anhydrous dichloromethane (200 mL) and stirred at 19°C under nitrogen atmosphere. To this, a solution diisopropyl carbodiimide (6.0 mL, 38.98 mmol) in dichloromethane (25 mL) was introduced over a period of 15 minutes and the mixture was stirred at 19°C for 4 hours. Reaction was monitored by TLC using 10percent methanol in dichloromethane as eluent and spray dried with p-anisaldehyde staining solution or observed under UV light. After complete consumption of cholesterol-diglycolic acid (2), the resultant hazy solution was cooled to -15°C and the solid separated was removed by filtration through a cotton pad and filtrates from this batch and recycled AUY922 (2.0 g) batch were combined and concentrated to a thick solution. [0093] Purification: The thick solution was loaded on a pre-packed silica gel column in dichloromethane (1500 g). Eluted with 1 -5percent methanol in dichloromethane. Fractions containing major product were concentrated to get pale yellow solid foam (11.50 g). The solid foam was subjected to another silica gel chromatographic purification by loading on a pre-packed silica gel column in dichloromethane (1500 g). The column was eluted with an isocratic eluent system with a solvent ratio of 3/0.5/96.5 methanol isopropanol/ dichloromethane. This process of purification on silica gel column was repeated until >95percent purity by HPLC and nmR was achieved. Alternatively, the product was passed through a reverse phase column (RP, C-18) in neat methanol with a loading ratio of 0.5 g per 240 g of C-18 column. Pure product fractions were collected and concentrated. Dried in vacuum oven for 18 hours to get pure AUY922-diglycolate-cholesterol (4) as off-white powder (4.95 g, 24percent· yield, HPLC purity 98percent at 230 nm). nmR (600 MHz, DMSO-de) : delta 10.42 (s, 1 H), 8.86 (t, J = 4 Hz, 1H), 7.23 (ABq, J = 8, 40 Hz, 4H), 6.96 (s, 1 H), 6.72 (s, 1H), 5.37 (bs, IH), 4.58-4.53 (m, 1H), 4.29 (s, 2H), 4.17 (s, 2H), 3.60-3.53 (m, 4H), 2.08 (bs, 2H), 3.33 (bs, 2H), 3.26-3.17 (m, 2H), 3.12-3.00 (m, IH), 2,40-2,30 (m, 6H), 2.05-1.90 (m, 2H), 1.90-1.75 (m, 3H), 1.65-1.45 (m, 5H), 1.44-1.20 (m, 6H), 1.19-0.95 (m, 17H), 0.94-0.91 (m, 9H), 0.88 (d, J = 4 Hz, 3H), 0.70 (s, 3H) ppm. ESI-MS Data: m/z = 950.59 [M+H].
  • 5
  • [ 747412-49-3 ]
  • [ 74124-79-1 ]
  • N-ε-4-methyltrityl-L-lysine [ No CAS ]
  • [ 75286-49-6 ]
  • [ 60-24-2 ]
  • 5-carboxy-2-(6-(dimethylamino)-3-(dimethyliminio)-3H-xanthen-9-yl)benzoate [ No CAS ]
  • C108H153N23O19S2 [ No CAS ]
  • C108H153N23O19S2 [ No CAS ]
  • 6
  • [ 747412-49-3 ]
  • [ 74124-79-1 ]
  • C84H130N15O15PolS3 [ No CAS ]
  • [ 75286-49-6 ]
  • [ 60-24-2 ]
  • C77H121N19O14S2 [ No CAS ]
  • C77H121N19O14S2 [ No CAS ]
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