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CAS No. : | 133831-28-4 | MDL No. : | MFCD00216479 |
Formula : | C11H9NO3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | KRDRROJESQUFMJ-UHFFFAOYSA-N |
M.W : | 203.19 | Pubchem ID : | 735867 |
Synonyms : |
|
Num. heavy atoms : | 15 |
Num. arom. heavy atoms : | 9 |
Fraction Csp3 : | 0.09 |
Num. rotatable bonds : | 3 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 54.97 |
TPSA : | 59.16 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.57 cm/s |
Log Po/w (iLOGP) : | 1.48 |
Log Po/w (XLOGP3) : | 1.36 |
Log Po/w (WLOGP) : | 1.77 |
Log Po/w (MLOGP) : | 0.74 |
Log Po/w (SILICOS-IT) : | 2.52 |
Consensus Log Po/w : | 1.57 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.2 |
Solubility : | 1.27 mg/ml ; 0.00627 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.2 |
Solubility : | 1.27 mg/ml ; 0.00624 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.31 |
Solubility : | 0.0986 mg/ml ; 0.000485 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.48 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | 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 |
---|---|---|
49.58% | With borane-THF In tetrahydrofuran at 50℃; for 1 h; Inert atmosphere | To a stirred solution of compound 27 (0.78 g, 3.84 mmol) in dry THF (30 mL) at°C under argon atmosphere, borane in THF (1M, 15.36 mL, 15.36 mmol) was added drop wise. The resulting reaction mass was stirred at 50 °C for 1 h. The progress of the reaction was monitored by TLC. After completion, the reaction mixture was quenched with sat. NH4C1 solution (50 mL) and extracted with ethyl acetate (3 X 50 mL). The combined organic layerswere dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to obtain theThe crude compound was purified by silica gel column chromatography using 10percentEtOAc/hexane to afford compound 28 (0.36 g, 49.5 8percent) as a brown solid. TLC: 30percentEtOAc/Hexane (Rf: 0.6); ‘H-NMR (400 MHz, DMSO-d6): ö 11.15 (s, 1H), 8.00 (s, 1H), 7.627.55 (m, 2H), 7.37 (s, 1H), 3.84 (s, 3H), 3.27 (s, 3H), LCMS Observed (m/z): 189.90 (M+1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
49.58% | With borane-THF; In tetrahydrofuran; at 50℃; for 1h;Inert atmosphere; | To a stirred solution of compound 27 (0.78 g, 3.84 mmol) in dry THF (30 mL) atC under argon atmosphere, borane in THF (1M, 15.36 mL, 15.36 mmol) was added drop wise. The resulting reaction mass was stirred at 50 C for 1 h. The progress of the reaction was monitored by TLC. After completion, the reaction mixture was quenched with sat. NH4C1 solution (50 mL) and extracted with ethyl acetate (3 X 50 mL). The combined organic layerswere dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to obtain theThe crude compound was purified by silica gel column chromatography using 10%EtOAc/hexane to afford compound 28 (0.36 g, 49.5 8%) as a brown solid. TLC: 30%EtOAc/Hexane (Rf: 0.6); ?H-NMR (400 MHz, DMSO-d6): oe 11.15 (s, 1H), 8.00 (s, 1H), 7.627.55 (m, 2H), 7.37 (s, 1H), 3.84 (s, 3H), 3.27 (s, 3H), LCMS Observed (m/z): 189.90 (M+1). |
A mixture of 3-formyl-1 H-indole-6-carboxylic acid methyl ester (5 g, 24.6 mmol), p-toluene- sulfonic acid (704 mg, 3.7 mmol) and p-toluenesulfonylhydrazide (5.49 g, 29.5 mmol) in a mixture of dimethylformamide (50 mL) and sulfolane (25 mL) is heated at 100C for 15 min. Then cooled to RT, before the addition of sodium cyanoborohydride (6.2 g, 98.4 mmol, 2 g portions after 10 min intervals). The resulting mixture is heated at 100C for 2 h, cooled to RT and poured into a mixture of ice and water (250 mL) leading to a white precipitate. Water (500 mL) is added, and the mixture is stirred for 30 min before filtration. The off-white solid is washed with warm water. Toluene is added and removed by rotary evaporation to afford the EPO <DP n="161"/>title compound as a yellow solid. TLC1 Rf (hexane/AcOEt 4:1)= 0.3. MS (LC-MS): [M+H]+= 188.1. tR (HPLC, Macherey-Nagel Nudeosil C18 column, 10-100% CH3CN/H2O/5 min, 100% CH3CN/3 min, CH3CN and H2O containing 0.1% TFA, flow: 1.5 mL/min): 5.13 min. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 16h; | To a solution of <strong>[133831-28-4]3-formylindole-6-carboxylic acid methyl ester</strong> (2.05 g, 10.1 mmol) and 4- methoxybenzyl chloride (1.4 mL, 10.1 mmol) in DMF (20 mL) was added K2CO3 (4.2 g, 30.3 mmol). After stirring at room temperature for 16 hr, the solution was diluted with ethyl acetate (200 ml) and washed with water (4 X 100 <n="97"/>ml). The organic layer was dried (MgSO4), filtered and concentrated to collect 3.25 g (99% yield) of 3- formylindoe-l-(4-methoxybenzyl)-6-carboxylic acid methyl ester as a tan solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With ammonium acetate; for 1h;Heating / reflux; | A. A suspension of methyl 3-formyl-6-indolecarboxylaate (10 g, 49.2 mmol) and ammonium acetate (2 g) in nitromethane (50 mL) was heated to reflux for 1 hour. After cooling, solid was collected by filtration and washed with methanol and dried under high vacuum to afford methyl 3- (2'-nitrovinyl)-6-carboxylate (11.2 g). All of the material was then submitted for hydrogenation in ethanol (100 mL) in the presence of 5% Pd/C (2 g) at 40 psi hydrogen for 2 hours. Catalyst was then removed by filtration and washed with ethanol. Evaporation of solvent under high vacuum gave methyl tryptamine-6-carboxylate (7.76 g), which was used in the next step without further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | To a solution of 3-formyl-lH-indole-6-carboxylic acid methyl ester (500 mg, 2.46 mmol), 4-morpholinoaniline (482.3 mg, 2.71 mmol) and dibutyltin dichloride (76 mg, 0.25 mmol) in THF was added phenylsilane (334 ul, 2.71 mmol). The mixture was stirred at room temperature overnight under nitrogen, THF was evaporated off the mixture and the residue was purified by flash chromatography (hexane/EtOAc, 20/80) to afford the title compound 123 (881 mg, 98%). H-NMR (DMSO) 8 : 8.00 (d, J= 1.0 Hz, 1H), 7.70 (d, J= 8.2 Hz, 1H) ; 7.58 (dd, J= 8.4, 1.6 Hz, 1H); 7.52 (d, J=2.0 Hz, 1H); 6.70 (d, J= 9.0 Hz, 2H); 6.59 (d, J= 9.0 Hz, 2H) ; 5.48 (t, J= 5.8 Hz, 1H); 4.31 (d, J=5.7 Hz, 2H); 3.83 (s, 3H) ; 3.68 (t, J=4.7 Hz, 4H) ; 2.86 (t, J=4.7 Hz, 4H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium methylate; In methanol; for 21h;Heating / reflux; | Sodium methoxide (1 g, 0.018 mol) was added in one portion to a mixture of 2-diethylphosphonyl-2H-1,4-benzoxazin-3(4H)-one (3.42 g, 0.012 mol) and 6-methoxycarbonylindol-3-carboxaldehyde (2.55 g, 0.012 mol) in methanol (60 ml). The reaction mixture was refluxed for 21 h, then cooled at room temperature and the precipitated solid was collected by filtration, washed with methanol and dried. Yield 2.78 g (87%) as a mixture of isomers. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Methyl 3-formylindole-6-carboxylate NMR (CDCl3, delta): 3.88 (3H, s), 7.83 (1H, dd, J=1, 8 Hz), 8.12 (1H, s), 8.16 (1H, d, J=8 Hz), 8.49 (1H, s), 12.45 (1H, br s). | ||
Methyl 3-formylindole-6-carboxylate NMR (CDCl3, delta): 3.88 (3H, s), 7.83 (1H, dd, J=1, 8 Hz), 8.12 (1H, s), 8.16 (1H, d, J=8 Hz), 8.49 (1H, s), 12.45 (1H, br s) | ||
EXAMPLE 2 Methyl 3-formyl-6-indolecarboxylate STR9 4.3 ml of phosphorus oxychloride was added dropwise with stirring and cooling (0 C.) to 14 ml of dimethylformamide and the mixture was stirred for a further 15 minutes at 0 C. After this, a solution of 8.6 g (0.049 mol) of the compound from Example 1 in 13 ml of dimethylformamide was added dropwise at room temperature, whereupon the temperature did not rise above 30 C. The solution was stirred for a further 3 hours at 35 C., added dropwise to ice water and adjusted to pH 7 using 2N sodium hydroxide solution. The solution was washed with methylene chloride and again adjusted to pH 1 using 2N hydrochloric acid. A precipitate deposited overnight, which was filtered off with suction and dried. Yield: 6.4 g (64% of theory) of white powder Rf (9:1, CH2 Cl2 (MeOH)=0.54 Rf (95:5, CH2 Cl2 /MeOH)=0.38 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium cyanoborohydride; toluene-4-sulfonic acid; In N-methyl-acetamide; (2S)-N-methyl-1-phenylpropan-2-amine hydrate; water; | REFERENCE EXAMPLE 30 Methyl 3-methyl-1 H-indole-6-carboxylate A mixture of methyl 3-formyl-1 H-indole-6-carboxylate (12.0 g), p-toluenesulphonic acid (2.0 g) and p-toluenesulphonylhydrazide (13.0 g) in a mixture of dimethylformamide (100 ml) and sulpholane (50 ml) was heated at 100 C. for 15 minutes and then cooled to room temperature. The mixture was treated with sodium cyanoborohydride (15.0 g, 5 g portions after 10 minute intervals), then heated at 100 C. for 2 hours. After cooling to ambient temperature the reaction mixture was treated with ice water (500 ml) giving a white precipitate. Water (1000 ml) was added and the mixture stirred for 30 minutes then filtered. The off-white solid was washed with warm water then azeotroped with toluene to yield the title compound (10.2 g) as a white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate; In N-methyl-acetamide; phosphorus pentaoxide; water; | EXAMPLE 3 Methyl 1-(2-ethoxycarbonyl)ethyl-3-formyl-6-indolecarboxylate STR10 3.9 g (0.019 mol) of indole aldehyde, of the compound from Example 2, 4.0 g (0.022 mol) of ethyl-3-bromopropionate, 5.3 g (0.038 mol) of potassium carbonate and 30 ml of dimethylformamide was stirred at 100 C. for 3 hours. The solvent was removed in vacuo and the residue was stirred with 50 ml of water and cooled to 5 C. The white amorphous precipitate was filtered off with suction, washed with water and dried in vacuo over phosphorus pentoxide. Yield: 5.3 g (90% of theory) Melting point: 129 C. Rf (9:1, CH2 Cl2 /MeOH)=0.85 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | Step A: 3-Formyl-1 /-/-indole-6-carboxylic acid; . To a solution of methyl 3- formyl-indole-6-carboxylic acid (4.0 g, 19.7 mmol) in tetrahydrofuran (THF):H2O (3:1 ; 100 ml_) was added 2 N LiOH (20 ml_, 39.4 mmol). After 24 h, the reaction mixture was partially concentrated and diluted with H2O (100 ml_). The solution was cooled to 0 0C and treated with cone. HCI until a precipitate formed. The solid was collected and dried under vacuum to provide 4.0 g (100%) of the title compound as a tan solid. 1H NMR (DMSO-c/6): 12.85 (br s, 1 H), 12.54 (br s, 1 H), 9.98 (s, 1 H), 8.49 (d, J = 4.0, 1 H), 8.17-8.14 (m, 2H), 7.83 (dd, J = 8.5, 1.9, 1 H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Synthesis of Compound 175 (Scheme AE) L-Alaninamide, N-[[1-[(2,6-dichlorophenyl)methyl]-3-(1-pyrrolidinylmethyl)-1H-indol-6-yl]carbonyl]-3,4-difluoro-L-phenylalanyl-N-(2-aminoethyl)-3-(4-pyridinyl)-(Compound 175) [0152] Methyl-3-formylindole-6-carboxylate AE1 (5.00 g, 24.6 mmol) was dissolved in dry DMF (66 mL) under nitrogen and cesium carbonate (8.01 g, 24.6 mmol) was added.The mixture was stirred at rt for 10 min. After stirring for 10 min, 2,6-dichlorobenzyl bromide (5.90 g, 24.6 mmol) was added and the reaction stirred at rt for 20 h.The reaction mixture was filtered and the filtrate was diluted with CH2Cl2, washed with equal volumes of H2O (5*), then dried (MgSO4) and evaporated in vacuo to a solid. The solid (3.59 g, 9.9 mmol) was dissolved in ClCH2CH2Cl:AcOH (100:1) under nitrogen, pyrrolidine (3.30 mL, 39.6 mmol) and NaB(OAc)3H (5.23 g, 24.7 mmol) were added and the mixture stirred at rt for 1.5 h. The reaction mixture was then diluted with EtOAc (200 mL), washed with H2O (2*100 mL) and brine (1*100 mL), then dried (NaSO4) and evaporated in vacuo to a solid. The solid (4.05 g, 9.7 mmol) was suspended in THF (100 mL) under nitrogen, KOSiMe3 (3.73 g, 29.1 mmol) was added and the reaction was stirred at rt for 72 h. Additional KOSiMe3 (1.24 g, 9.7 mmol) was added and the reaction was stirred at 40 C. for 6 h. After cooling to rt, the reaction mixture was evaporated in vacuo and dried. The resulting residue was dissolved in H2O (30 mL), the pH was adjusted to about pH 6 with 6N HCl and the product was extracted with EtOAc, which precipitated a solid. The yellow solid was filtered and dried to afford AE2. The resin AE3 was then agitated in DMF (8 mL) with AE2 (0.097 g, 0.24 mmol), HOBT (0.041 g, 0.30 mmol) and DCC (0.062 g, 0.30 mmol) at rt for 20 h. The solution was drained; the resin was then washed with DMF (3*), MeOH (3*) and CH2Cl2 (3*) and dried in vacuo for about 2 h. The resin was combined with TFA:CH2Cl2:anisole (30:70:1.0, 8 mL) and stirred at about rt for about 1.5 h. The resin was filtered and the filtrate was blown down with nitrogen overnight to an oil, which was triturated with ether (4*) to give Compound 175 as a tan solid. 1H NMR (CD3OD) delta 8.55 (d, J=6.1, 2H), 8.20 (s, 1H), 7.84-7.79 (m, 3H), 7.64-7.38 (m, 5H), 7.25-7.11 (m, 3H), 5,71 (s, 2H), 4.78-4.71 (m, 2H), 4.52 (s, 2H), 3.55-3.01 (m, 12H), 2.11-1.97 (m, 4H). ES-MS m/z 776 (MH+). |
Tags: 133831-28-4 synthesis path| 133831-28-4 SDS| 133831-28-4 COA| 133831-28-4 purity| 133831-28-4 application| 133831-28-4 NMR| 133831-28-4 COA| 133831-28-4 structure
[ 312973-24-3 ]
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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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