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CAS No. : | 62996-74-1 | MDL No. : | MFCD18252446 |
Formula : | C28H26N4O3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 466.53 | Pubchem ID : | - |
Synonyms : |
STS;AM-2282;Staurosporin.;CGP-39360;CGP 41251;Antibiotic 230;Stsp;AM-2282,Antibiotic AM-2282;Antibiotic AM-2282
|
Num. heavy atoms : | 35 |
Num. arom. heavy atoms : | 20 |
Fraction Csp3 : | 0.32 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 5.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 140.84 |
TPSA : | 72.94 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | Yes |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | Yes |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.62 cm/s |
Log Po/w (iLOGP) : | 3.33 |
Log Po/w (XLOGP3) : | 3.56 |
Log Po/w (WLOGP) : | 3.96 |
Log Po/w (MLOGP) : | 3.01 |
Log Po/w (SILICOS-IT) : | 3.5 |
Consensus Log Po/w : | 3.47 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -5.27 |
Solubility : | 0.00253 mg/ml ; 0.00000542 mol/l |
Class : | Moderately soluble |
Log S (Ali) : | -4.78 |
Solubility : | 0.00779 mg/ml ; 0.0000167 mol/l |
Class : | Moderately soluble |
Log S (SILICOS-IT) : | -7.11 |
Solubility : | 0.0000362 mg/ml ; 0.0000000776 mol/l |
Class : | Poorly soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 2.0 |
Synthetic accessibility : | 5.33 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302 | Packing Group: | N/A |
GHS Pictogram: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
~ 91.5% | In ethanol; water; at 70℃;Product distribution / selectivity; | A reactor is charged with <strong>[62996-74-1]staurosporine</strong> B2 with benzoic anhydride, absolute ethanol and water. The reaction mixture is heated to about 7O0C and aged. At the end of the reaction EPO <DP n="15"/>time, the reaction mixture is seeded with crystalline form Il of Lambda/-benzoyl-<strong>[62996-74-1]staurosporine</strong> suspended in absolute ethanol. After aging, absolute ethanol and water are slowly added to the suspension. The suspension is aged again, then cooled to about O0C before crystalline form Il of Lambda/-benzoyl-<strong>[62996-74-1]staurosporine</strong> is isolated by filtration. The wet cake of Lambda/-benzoyl-<strong>[62996-74-1]staurosporine</strong> is rinsed multiple times with absolute ethanol and then dried in a vacuum oven at an external temperature of 6O0C and a vacuum of approximately 5-30 mbar for about 16 hours to obtain the product: 39.70 g, dried cake : 27.2 g theory quell. Yield: approximately 91.5% of theory quell related to B1 100%. |
~ 82% | In ethanol; water; at 70℃;Product distribution / selectivity; | A reactor is charged with <strong>[62996-74-1]staurosporine</strong> B2 with benzoic anhydride, ethanol and water. The reaction mixture is heated to about 70C and aged. The solution is filtered and the filter apparatus and filter cake are washed multiple times with ethanol. The filtered solution is transferred to another reactor and cooled to about 600C. Water is slowly added to the solution. The solution is seeded with amorphous Lambda/-benzoyl-<strong>[62996-74-1]staurosporine</strong>. The suspension is aged, then cooled to about 2O0C then aged again. Lambda/-benzoyl-<strong>[62996-74-1]staurosporine</strong> is isolated by filtration. The wet cake of Lambda/-benzoyl-<strong>[62996-74-1]staurosporine</strong> is rinsed multiple times with absolute ethanol. The wet cake is then re-suspended in the filter apparatus in ethanol, aged at about 25C then cooled to about 0-50C and aged again. This process step may be repeated multiple times. N- benzoyl-<strong>[62996-74-1]staurosporine</strong> is isolated by filtration. The wet cake is dried in a vacuum oven at an external temperature of about 400C and a vacuum of approximately 10-20 mbar for about 24 hours to obtain product: 35-40 g dried cake: 27 g theory quell. Yield: approximately 82% of theory theory quell related to B1 100%. The use of ethanol in the above reaction may be replaced with THF. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
A reactor is charged with <strong>[62996-74-1]staurosporine</strong> B1 and ethanol. The suspension is heated to about 700C. Methanesulfonic acid is added to the suspension and the obtained solution is aged. Activated charcoal and Hyflo are added and the mixture is aged. The suspension is filtered and the filter apparatus and filter cake are washed multiple times with ethanol. The clear filtered solution is transferred to another reactor and cooled to about 600C. Triethylamine diluted in ethanol is added slowly to the reaction mixture. Afterwards, the suspension is cooled EPO <DP n="14"/>to about 200C and aged. The <strong>[62996-74-1]staurosporine</strong> B2 is isolated by filtration. The product is rinsed multiple times with ethanol. | ||
In ethanol; benzyl alcohol; at 0 - 90℃; for 2h;Crystallization;Purification / work up; | A reactor is charged with <strong>[62996-74-1]staurosporine</strong> B1 and benzyl alcohol. The suspension is heated to about 850C and aged. Activated charcoal and Hyflo are added to the solution and the mixture is aged again. The suspension is filtered at about 9O0C. The filter apparatus and filter cake are washed multiple times with benzyl alcohol. The clear filtered solution is transferred to another reactor and cooled to about 70C. The solution is seeded with <strong>[62996-74-1]staurosporine</strong> B2 suspended in ethanol. Afterwards, ethanol is added to the suspension and the suspension is aged, then cooled to about 00C. The suspension is again aged for at least 2 hours at about 0C. The <strong>[62996-74-1]staurosporine</strong> B2 is isolated by filtration. The product is rinsed multiple times with ethanol. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Prepared a solution of benzoic acid (315 mg; 2.6 mmol) and HBTU (1076 mg; 2.8 mmol) in DMF cool the solution at lOC and add N,N-Diisopropyl ethyalmine (1.37 mL; 7.7 mmol). Stirred the reaction mixture for 90 minutes at 25C. To the reaction mixture charged <strong>[62996-74-1]staurosporine</strong> (600 mg; 1.3 mmol). Stirred the reaction mixture for 4 hours. The reaction mass is diluted with water followed by extraction with ethyl acetate. The organic layer is dried over sodium sulphate and distilled under vacuum to get residue. Triturated the residue with ether. The solid obtained is filtered and dried to get Midostaurin. (Yield: 61%; purity by HPLC: 88%). Midostaurin as obtained is purified by solvent - anti-solvent precipitation procedure using IPA and water. (Purity by HPLC: 97%) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With triethylamine; In dichloromethane; at 20℃;Inert atmosphere; | Under the protection of argon, the cross spore alkali (1.86 g, 4.0 mmol) for 100 ml dichloromethane dissolved, at room temperature by adding 10 ml triethylamine andN,N' - Sulfur carbonyl diimidazole (1.3 g, 8.0 mmol), the reaction overnight at room temperature. The reaction solution is poured into 100 ml ice water, dichloromethane extraction, anhydrous sodium sulfate after drying the organic phase concentration, silica gel column chromatography separation, dichloromethane: methanol=20:1 (v/v) elute and get the 3' -N- (1 - Imidazole sulfur on behalf of the carboxamido) cross spore alkali 1.9 g, yield 82%, |
78% | With triethylamine; In dichloromethane; at 20℃; | Et3N (1.0mL) and N,N?-thiocarbonyldiimidazole (214mg, 1.2mmol) were added sequentially to a solution of <strong>[62996-74-1]staurosporine</strong> (186mg, 0.4mmol) in CH2Cl2 (10mL) at rt. After stirring overnight, the reaction flask contents were poured into cold water (20mL) and extracted with CH2Cl2 (3×30mL). The combined organic layers were then washed with brine, dried over anhydrous Na2SO4, and concentrated in vacuo. The residue was purified by FCC eluting with CH2Cl2-MeOH (20:1) to provide 3?-N-(1H-imidazole-1-carbamothioyl)<strong>[62996-74-1]staurosporine</strong> (11, 180mg, 0.312mmol, 78% yield) as a light yellow solid; Rf 0.62 (20:1 CH2Cl2-MeOH); [alpha]D18 +362 (c 0.07, CHCl3); IR (KBr): 3723, 1673, 1584, 1456, 1398, 1344, 1315, 1226, 1119, 749, 615cm-1; 1H NMR (500MHz, DMSO-d6) delta 9.32 (d, J=7.9Hz, 1H), 8.63 (s, 1H), 8.12 (s, 1H), 8.07 (d, J=7.7Hz, 1H), 8.03 (d, J=8.5Hz, 1H), 7.64 (d, J=7.2Hz, 1H), 7.59 (br s, 1H), 7.51 (t, J=7.4Hz, 1H), 7.50 (t, J=7.7, 1H),7.37 (t, J=7.4Hz, 1H), 7.32 (t, J=7.5Hz, 1H), 7.13 (br s, 1H), 7.06 (m, 1H), 5.47 (m, 1H), 5.01 (s, 2H), 4.79 (br s, 1H), 3.06 (s, 3H), 3.05 (m, 1H), 2.73 (s, 3H), 2.44 (s, 3H), 2.43 (m, 1H); 13C NMR (125MHz, DMSO-d6) delta 179.3, 171.9, 138.8, 137.7, 136.2, 132.7, 129.3, 129.0, 125.8, 125.4, 125.2 (2×C), 123.9, 122.7, 121.6, 120.5, 119.9, 119.6, 119.6, 115.3, 114.3, 113.5, 108.9, 94.8, 81.9 (2×C), 60.4, 58.1, 45.5, 38.2, 29.4, 27.1; HRESI-MS m/z 577.2031 [M+H]+ (calcd for C32H29N6O3S, 577.2022). Compound 11 (80mg, 0.14mmol) was dissolved in 10mL of CH3CN and treated with MeI (86muL, 1.39mmol) at room temperature. The mixture was stirred at rt for 24h. The solvent was removed under vacuum and the residue was washed with 50mL of PE-CH2Cl2 (1:1) to provide the thiocarbamoylimidazolium salt 12 (75mg, 0.105mmol, 76% yield) as a light yellow powder; [alpha]D18 +267 (c 0.07, MeOH); IR (KBr): 1680, 1549, 1531, 1515, 1460, 1347, 1312, 747cm-1; 1H NMR (500MHz, DMSO-d6) delta 9.71 (s, 1H), 9.31 (d, J=8.0Hz, 1H), 8.65 (s, 1H), 8.16 (br s, 1H), 8.09 (d, J=7.7Hz, 1H), 8.05 (d, J=8.3Hz, 1H), 7.87 (br s, 1H), 7.64 (d, J=7.7Hz, 1H), 7.53 (t, J=7.3Hz, 1H), 7.51 (t, J=7.7Hz, 1H), 7.39 (t, J=7.4Hz, 1H), 7.32 (t, J=7.5Hz, 1H), 7.18 (t, J=7.1Hz, 1H), 5.40m, 1H), 5.01 (s, 2H), 4.77 (br s, 1H), 3.92 (s, 3H), 3.09 (s, 3H), 3.12 (m, 1H), 2.75 (s, 3H), 2.46 (s, 3H), 2.46 (m, 1H); 13C NMR (125MHz, DMSO-d6) delta 174.3, 171.8, 138.8, 138.1, 136.2, 132.7, 129.2, 127.0, 127.0, 125.8, 125.4, 125.3, 123.9, 123.8, 122.8, 121.6, 120.6, 119.7, 119.6, 115.4, 114.4, 113.5, 108.9, 94.7, 81.8, 81.2, 60.5, 59.3, 45.5, 38.6, 36.5, 29.4, 26.8; HRESI-MS m/z 591.2164 [M-I]+ (calcd for C33H31N6O3S, 591.2173). |
78% | With triethylamine; In dichloromethane; at 20℃; | A solution of <strong>[62996-74-1]staurosporine</strong> (186 mg, 0.4 mmol)Dissolved in 10 mL of methylene chloride,1 mL of triethylamine and N, N'-thiocarbonyldiimidazole (214 mg, 1.2 mmol) were added at room temperature,Overnight at room temperature.The reaction solution was poured into 20 mL of ice water,Dichloromethane extraction,The organic phase was dried over anhydrous sodium sulfate and concentrated,Silica gel column chromatography,Dichloromethane: methanol = 20: 1 (v / v)3'-N- (1-imidazolylthio)<strong>[62996-74-1]Staurosporine</strong>(168) 180mg,Yield 78%. |
78% | With triethylamine; In dichloromethane; at 20℃; | The <strong>[62996-74-1]staurosporine</strong> (186 mg, 0.4 mmol) was dissolved in 10 mL of dichloromethane,1 mL of triethylamine and N, N'-thiocarbonyldiimidazole (214 mg, 1.2 mmol) were added at room temperature,Room temperature overnight reaction.The reaction solution was poured into 20 mL of ice water, extracted with dichloromethane, dried over anhydrous sodium sulfate and then concentrated. The column was separated by silica gel column chromatography,Dichloromethane: methanol = 20: 1 (v / v)Eluted to give 180 mg of 3'-N- (1-imidazolylthioformyl) <strong>[62996-74-1]staurosporine</strong> (168) in a yield of 78%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | In tetrahydrofuran; for 12h;Reflux; | N,N'-carbonyldiimidazole (140 mg, 0.86 mmol) was added to a solution of <strong>[62996-74-1]staurosporine</strong> (200 mg, 0.43 mmol) in THF (10 mL). The mixture was refluxed for 12 h, and concentrated in vacuo. The residue was purified by FCC eluting with CH2Cl2-MeOH (20:1) to provide 13 (202 mg, 0.36 mmol, 84% yield) as a light yellow solid; Rf 0.58 (20:1 CH2Cl2-MeOH); [alpha]D18 +176 (c 0.07, CHCl3); IR (KBr): 1681, 1531, 1514, 1459, 1393, 1313, 1220, 749 cm-1; 1H NMR (500 MHz, DMSO-d6) delta 9.31 (d, J=7.9 Hz, 1H), 8.68 (s, 1H), 8.61 (s, 1H), 8.07 (d, J=7.8 Hz, 1H), 8.01 (d, J=8.5 Hz, 1H), 7.79 (br s, 1H), 7.59 (d, J=8.2 Hz, 1H), 7.51 (t, J=8.2 Hz, 1H), 7.49 (t, J=8.2 Hz, 1H),7.37 (t, J=7.7 Hz, 1H), 7.35 (br s, 1H), 7.31 (t, J=7.5 Hz, 1H), 7.04 (dd, J=8.5, 5.6 Hz, 1H), 5.00 (s, 2H), 4.68 (m, 1H), 4.50 (br s, 1H), 2.96 (m, 1H), 2.89 (s, 3H), 2.61 (s, 3H), 2.40 (m, 1H), 2.39 (s, 3H); 13C NMR (125 MHz, DMSO-d6) delta 172.0, 150.8, 138.6, 137.2, 136.3, 132.6, 129.5, 125.9, 125.8, 125.5, 125.5, 125.3, 123.9, 122.8, 121.7, 120.6, 119.7, 119.6, 119.5, 115.2, 114.3, 113.2, 109.0, 94.7, 83.2, 82.1, 60.2, 52.3, 45.5, 33.2, 28.9, 27.0; HRESI-MS m/z 561.2242 [M+H]+ (calcd for C32H29N6O4, 561.2245). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
25% | With N-ethyl-N,N-diisopropylamine; In 1-methyl-pyrrolidin-2-one; at 20℃; for 24h; | Thirty-seven point nine milligrams (0.081 mmol) of STU was dissolved in 500 mul of NMP solution, and 27 mul of DIEA and 29.5 mg (0.12 mmol) of 4-bromomethyl-1,1?-biphenyl (hereinafter abbreviated as AK46363) to obtain a reactant. The reactant reacted at room temperature for 24 hours. After the reaction, dichloromethane and water was used for extraction, and an organic phase was collected. Then, the high-performance liquid chromatograph was used for purification. Then, elution was performed with dichloromethane and methanol at a ratio of 20:1. After collecting the eluent, it was dried by concentrating under a reduced pressure, and 12.8 mg of compound 9 was obtained. Yield: 25%. The analytical conditions for the high-performance liquid chromatograph were dissolving the obtained compound 9 in double-distilled water, using the Supelco RP-C18 column (5 m, 4.6×250 mm) for purification, and performing UV (with wavelengths of 254 nm and 300 nm) detection. The solutions used as a mobile phase were deionized water containing 0.1% formic acid (solution A) and methanol containing 0.1% of formic acid (solution B). The flow rate was 1 ml/min. Forty percents of solution B was used for elution for 7.5 minutes, a gradient of 40% to 60% of solution B was used for elution for 7.5 minutes, and then 100% of solution B was used for continual elution for 10 minutes. A single absorption peak was found at the retention time of about 12.45 minutes. The absorption peak indicated compound 9. ESI-MS (m/z): calculated value: 632.58, and measured value: 633.2 [M+H]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88.6% | With potassium tert-butylate; oxygen; In dimethyl sulfoxide; at 20℃; for 6h; | In a 25 mL two-necked reaction flask filled with oxygen,A solution of <strong>[62996-74-1]staurosporine</strong> (6.6 mg, 0.1 mmol),Dissolved in 3 mL of DMSO,An excess of potassium tert-butoxide,Room temperature reaction 6h,Water was added to terminate the reaction,Ethyl acetate was extracted three times,Vacuum evaporated,After separation by gel column chromatography,Methanol elution was7-oxo-ylidene <strong>[62996-74-1]staurosporine</strong>(135a) 42.5mg,Yield 88.6%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83.3% | With triethylamine; In dichloromethane; at 20℃; for 4h;Inert atmosphere; | Under argon protection,In a 25 mL two-necked reaction flask,A solution of <strong>[62996-74-1]staurosporine</strong> (46.6 mg, 0.1 mmol),Dissolved in 3 mL of methylene chloride,An excess of triethylamine was added dropwise,Then p-fluorobenzenesulfonyl chloride was added,Stirring reaction at room temperature 4h,Water was added to terminate the reaction,Dichloromethane extraction,And dried over anhydrous Na2SO4,Vacuum evaporated,After separation by gel column chromatography,Methanol elution was3'-N-p-fluorobenzenesulfonyl<strong>[62996-74-1]Staurosporine</strong>(130)Yield 83.3%. |
83.3% | With triethylamine; In dichloromethane; at 20℃; for 4h;Inert atmosphere; | Argon under the protection,In a 25 mL two-necked reaction flask, <strong>[62996-74-1]staurosporine</strong> (46.6 mg, 0.1 mmol) was added,Dissolved in 3 mL of dichloromethane, excess triethylamine was added dropwise,Then adding p-fluorobenzenesulfonyl chloride, stirring at room temperature for 4 h,The reaction was quenched with water, extracted with dichloromethane, dried over anhydrous Na2SO4, evaporated in vacuo,After gel column chromatography,Methanol was eluted with 52.0 mg of 3'-N-p-fluorobenzenesulfonic acid <strong>[62996-74-1]staurosporine</strong> (130) 52 mg, and the yield was 83.3%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | At 0 , in THF (5mL) was dissolved <strong>[62996-74-1]staurosporine</strong> (60mg, 0.129mmol),Was added diisopropylethylamine(64 [mu] L, 0.38 mmol)And triphosgene (19 mg, 0.064 mmol), stirred at room temperature for 2 h, poured into ice water,Extraction with ethyl acetate (2 x 30 mL)Brine washing (2 × 30mL),The organic phase was dried over anhydrous sodium sulphate,Steam to dry.The crude product was dissolved in THF (3 mL)Diisopropylethylamine (127 [mu] L, 0.77 mmol),Imidazole (18 mg, 0.25 mmol) and p-dimethylaminopyridine (31.5 mg, 0.258 mmol),60 stirring reaction 2h,Poured into ice water,Extraction with ethyl acetate (2 x 30 mL)Brine washing (2 × 30mL),The organic phase was dried over anhydrous sodium sulphate,Steam to dry.Silica gel column chromatography,Dichloromethane: methanol = 50: 1 (v / v)To give a light yellow solid:3'-N- (1- formyl imidazole) of <strong>[62996-74-1]staurosporine</strong> (167) 56mg,Yield 80% |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 20℃; for 2h; | The <strong>[62996-74-1]staurosporine</strong> (46.6 mg, 0.1 mmol) was used5 mL of dichloromethane was dissolved,Adding a catalytic amount of DMAP,Dicyclohexylcarbodiimide(24.7 mg, 0.12 mmol)And chlorambucil(36.4 mg, 0.12 mmol)The reaction was carried out at room temperature for 2 hours,Poured into ice water,Dichloromethane extraction,Dried over anhydrous sodium sulfate and concentrated,Silica gel column chromatography,Petroleum ether: ethyl acetate = 1: 1 (v / v)3'-N- [4- [4- (N, N-Bis (2-chloroethyl)Amino) phenyl]Butyryl]<strong>[62996-74-1]Staurosporine</strong> (184)60.1 mg,Yield 80% |
80% | With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 20℃; for 2h; | The <strong>[62996-74-1]staurosporine</strong> (46.6 mg, 0.1 mmol) was dissolved in 5 mL of dichloromethane,Followed by adding a catalytic amount of DMAP,Dicyclohexylcarbodiimide (24.7 mg, 0.12 mmol)And chlorambucil (36.4 mg, 0.12 mmol) at room temperature for 2 hours,Poured into ice water, extracted with dichloromethane, dried over anhydrous sodium sulfate and concentrated,Silica gel column chromatography, petroleum ether: ethyl acetate = 1: 1 (v / v) elution of 3'-N- [4- [4- (N, N-bis (2-chloroethyl) amino) phenyl] butyryl]<strong>[62996-74-1]staurosporine</strong> (184)60.1mg, yield 80% |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88.6% | With potassium tert-butylate; oxygen; In dimethyl sulfoxide; at 20℃; for 6h; | In a 25 mL two-necked reaction flask filled with oxygen,Trees were added <strong>[62996-74-1]staurosporine</strong> (6.6 mg, 0.1 mmol)Dissolved in 3mL DMSO, add excess potassium tert-butoxide, room temperature reaction 6h,The reaction was terminated with water, extracted three times with ethyl acetate, evaporated in vacuo and then separated by gel column chromatography,Methanol was eluted with a yield of 88.6% of 7-oxo stearate (135a). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | 0 C,Dissolve <strong>[62996-74-1]staurosporine</strong> (60 mg, 0.129 mmol) in THF (5 mL)Diisopropylethylamine (64 [mu] L, 0.38 mmol) and triphosgene (19 mg, 0.064 mmol)Stirred at room temperature for 2 h, poured into ice water, extracted with ethyl acetate (2 x 30 mL)Brine (2 x 30 mL) and the organic phase was dried over anhydrous sodium sulfate and evaporated to dryness. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine; In N,N-dimethyl-formamide; | 210 g from the obtained product <strong>[62996-74-1]staurosporine</strong> was dissolved in dimethyl formamide (DMF, 5.25 L). 61.5 ml Triethyl-amine was added and benzoyl-chloride (41 mL) was dropped into the mixture. After reaction completion the mixture was diluted with isoButhyl-acetate (iBuOAc, 26.25 L), washed with saturated NaHCO3 solution and water. Crude Midostaurin was precipitated after evaporation of organic phase to 1/10 volume and addition of n-Heptane (45 L) at room temperature (25C). The suspension was cooled to 5C for 18 hours, filtered and dried at 60C, under reduced pressure to give N-[(9S,10R,11R,13R)-2,3,10,11,12,13 -hexahydro-10-methoxy-9-methyl-1-oxo-9,13-epoxy-1H,9H-diindolo[1,2,3-gh:3,2?,1?-1m]pyrrolo[3,4-j][1,7]benzodiazonin-11-yl]-N-methylbenzamide |
Tags: 62996-74-1 synthesis path| 62996-74-1 SDS| 62996-74-1 COA| 62996-74-1 purity| 62996-74-1 application| 62996-74-1 NMR| 62996-74-1 COA| 62996-74-1 structure
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P272 | Contaminated work clothing should not be allowed out of the workplace. |
P273 | Avoid release to the environment. |
P280 | Wear protective gloves/protective clothing/eye protection/face protection. |
P281 | Use personal protective equipment as required. |
P282 | Wear cold insulating gloves/face shield/eye protection. |
P283 | Wear fire/flame resistant/retardant clothing. |
P284 | Wear respiratory protection. |
P285 | In case of inadequate ventilation wear respiratory protection. |
P231 + P232 | Handle under inert gas. Protect from moisture. |
P235 + P410 | Keep cool. Protect from sunlight. |
Response | |
Code | Phrase |
P301 | IF SWALLOWED: |
P304 | IF INHALED: |
P305 | IF IN EYES: |
P306 | IF ON CLOTHING: |
P307 | IF exposed: |
P308 | IF exposed or concerned: |
P309 | IF exposed or if you feel unwell: |
P310 | Immediately call a POISON CENTER or doctor/physician. |
P311 | Call a POISON CENTER or doctor/physician. |
P312 | Call a POISON CENTER or doctor/physician if you feel unwell. |
P313 | Get medical advice/attention. |
P314 | Get medical advice/attention if you feel unwell. |
P315 | Get immediate medical advice/attention. |
P320 | |
P302 + P352 | IF ON SKIN: wash with plenty of soap and water. |
P321 | |
P322 | |
P330 | Rinse mouth. |
P331 | Do NOT induce vomiting. |
P332 | IF SKIN irritation occurs: |
P333 | If skin irritation or rash occurs: |
P334 | Immerse in cool water/wrap n wet bandages. |
P335 | Brush off loose particles from skin. |
P336 | Thaw frosted parts with lukewarm water. Do not rub affected area. |
P337 | If eye irritation persists: |
P338 | Remove contact lenses, if present and easy to do. Continue rinsing. |
P340 | Remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P341 | If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P342 | If experiencing respiratory symptoms: |
P350 | Gently wash with plenty of soap and water. |
P351 | Rinse cautiously with water for several minutes. |
P352 | Wash with plenty of soap and water. |
P353 | Rinse skin with water/shower. |
P360 | Rinse immediately contaminated clothing and skin with plenty of water before removing clothes. |
P361 | Remove/Take off immediately all contaminated clothing. |
P362 | Take off contaminated clothing and wash before reuse. |
P363 | Wash contaminated clothing before reuse. |
P370 | In case of fire: |
P371 | In case of major fire and large quantities: |
P372 | Explosion risk in case of fire. |
P373 | DO NOT fight fire when fire reaches explosives. |
P374 | Fight fire with normal precautions from a reasonable distance. |
P376 | Stop leak if safe to do so. Oxidising gases (section 2.4) 1 |
P377 | Leaking gas fire: Do not extinguish, unless leak can be stopped safely. |
P378 | |
P380 | Evacuate area. |
P381 | Eliminate all ignition sources if safe to do so. |
P390 | Absorb spillage to prevent material damage. |
P391 | Collect spillage. Hazardous to the aquatic environment |
P301 + P310 | IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. |
P301 + P312 | IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell. |
P301 + P330 + P331 | IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. |
P302 + P334 | IF ON SKIN: Immerse in cool water/wrap in wet bandages. |
P302 + P350 | IF ON SKIN: Gently wash with plenty of soap and water. |
P303 + P361 + P353 | IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower. |
P304 + P312 | IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell. |
P304 + P340 | IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing. |
P304 + P341 | IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P305 + P351 + P338 | IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. |
P306 + P360 | IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes. |
P307 + P311 | IF exposed: call a POISON CENTER or doctor/physician. |
P308 + P313 | IF exposed or concerned: Get medical advice/attention. |
P309 + P311 | IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician. |
P332 + P313 | IF SKIN irritation occurs: Get medical advice/attention. |
P333 + P313 | IF SKIN irritation or rash occurs: Get medical advice/attention. |
P335 + P334 | Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages. |
P337 + P313 | IF eye irritation persists: Get medical advice/attention. |
P342 + P311 | IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician. |
P370 + P376 | In case of fire: Stop leak if safe to Do so. |
P370 + P378 | In case of fire: |
P370 + P380 | In case of fire: Evacuate area. |
P370 + P380 + P375 | In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion. |
P371 + P380 + P375 | In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion. |
Storage | |
Code | Phrase |
P401 | |
P402 | Store in a dry place. |
P403 | Store in a well-ventilated place. |
P404 | Store in a closed container. |
P405 | Store locked up. |
P406 | Store in corrosive resistant/ container with a resistant inner liner. |
P407 | Maintain air gap between stacks/pallets. |
P410 | Protect from sunlight. |
P411 | |
P412 | Do not expose to temperatures exceeding 50 oC/ 122 oF. |
P413 | |
P420 | Store away from other materials. |
P422 | |
P402 + P404 | Store in a dry place. Store in a closed container. |
P403 + P233 | Store in a well-ventilated place. Keep container tightly closed. |
P403 + P235 | Store in a well-ventilated place. Keep cool. |
P410 + P403 | Protect from sunlight. Store in a well-ventilated place. |
P410 + P412 | Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF. |
P411 + P235 | Keep cool. |
Disposal | |
Code | Phrase |
P501 | Dispose of contents/container to ... |
P502 | Refer to manufacturer/supplier for information on recovery/recycling |
Physical hazards | |
Code | Phrase |
H200 | Unstable explosive |
H201 | Explosive; mass explosion hazard |
H202 | Explosive; severe projection hazard |
H203 | Explosive; fire, blast or projection hazard |
H204 | Fire or projection hazard |
H205 | May mass explode in fire |
H220 | Extremely flammable gas |
H221 | Flammable gas |
H222 | Extremely flammable aerosol |
H223 | Flammable aerosol |
H224 | Extremely flammable liquid and vapour |
H225 | Highly flammable liquid and vapour |
H226 | Flammable liquid and vapour |
H227 | Combustible liquid |
H228 | Flammable solid |
H229 | Pressurized container: may burst if heated |
H230 | May react explosively even in the absence of air |
H231 | May react explosively even in the absence of air at elevated pressure and/or temperature |
H240 | Heating may cause an explosion |
H241 | Heating may cause a fire or explosion |
H242 | Heating may cause a fire |
H250 | Catches fire spontaneously if exposed to air |
H251 | Self-heating; may catch fire |
H252 | Self-heating in large quantities; may catch fire |
H260 | In contact with water releases flammable gases which may ignite spontaneously |
H261 | In contact with water releases flammable gas |
H270 | May cause or intensify fire; oxidizer |
H271 | May cause fire or explosion; strong oxidizer |
H272 | May intensify fire; oxidizer |
H280 | Contains gas under pressure; may explode if heated |
H281 | Contains refrigerated gas; may cause cryogenic burns or injury |
H290 | May be corrosive to metals |
Health hazards | |
Code | Phrase |
H300 | Fatal if swallowed |
H301 | Toxic if swallowed |
H302 | Harmful if swallowed |
H303 | May be harmful if swallowed |
H304 | May be fatal if swallowed and enters airways |
H305 | May be harmful if swallowed and enters airways |
H310 | Fatal in contact with skin |
H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
H313 | May be harmful in contact with skin |
H314 | Causes severe skin burns and eye damage |
H315 | Causes skin irritation |
H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
Sorry,this product has been discontinued.
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