Structure of 1877-64-1
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CAS No. : | 1877-64-1 |
Formula : | C9H10O4S |
M.W : | 214.24 |
SMILES Code : | CS(=O)(=O)C1=CC=CC(CC(O)=O)=C1 |
MDL No. : | MFCD03426066 |
Boiling Point : | No data available |
InChI Key : | RUGDYDBEYAHJCD-UHFFFAOYSA-N |
Pubchem ID : | 2761035 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H332-H335 |
Precautionary Statements: | P280-P305+P351+P338-P310 |
* 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 |
---|---|---|
With 1,1'-carbonyldiimidazole; In dichloromethane; at 20℃; for 3.0h; | EXAMPLE 4; This Example illustrates the preparation of 7V-(l-{(3JR)-3-(3,5-difluorophenyl)-3-[l-(methylsulfonyl)piperidin-4-yl]propyl}piperidin-4-yl)-A'-ethyl-2-[3-(methylsulfonyl)phenyl]acetamide.; o=s=o 3-(Methylsulfonyl)phenylacetic acid (96 mg) was disolved in dichloromethane (5 ml)and carbonyldiimidazole (73 mg) added. The reaction mixture was stirred at roomtemperature for 3hours. 7V-(l-{(3^)-3-(3,5-Difluorophenyl)-3-[l-(methylsulfonyl)piperidin-4-yl]propyl}piperidin-4-yl)-./V-ethylamme (200 mg) in dichloromethane (5 ml) was added andthe reaction mixture was allowed to stand at room temperature for 72 hours. PS isocyanateresin (1. mm/g) (0.5 g) was added and the reaction mixture stirred at room temperature for2hours, then filtered and evaporated. The residue was purified by column chromatographyeluting with ethyl acetate-20%methanol/ethyl acetate to yield the title compound as a foam(105 mg).NMR CDC13: 1.0-2.1 (m, 21H), 2.3-2.6 (m, 3H), 2.65 (s, 3H), 2.9 (s, 3H), 3.3 (m, 2H),3.65 (d, 1H), 3.7 (m, 2H), 3.75 (d, 1H), 6.6 (m, 3H), 7.5 (m, 2H), 7.75 (m, 2H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
31% | With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃; | N-[5-Chloro-2-(5-oxo-4, 5-dihydro-[1 , 2, 4]oxadiazol-3-yl)-phenyl]-2-(3-methanesulfonyl- phenyl)-acetamide (10); To a suspension of commercial 3-(methylsulfonyl)phenylacetic acid (0.25 g, 1 eq) in dichloromethane (15 ml), EDC HCI (0.447 g, 2 eq) and DMAP (0.428 g, 3 eq) are added. The resulting brown solution is stirred for 10 min and 3-(2-amino-4-chloro- phenyl)-4H-[1 ,2,4]oxadiazol-5-one (0.247 g, 1 eq) prepared as described by Valgeirsson et al. in Journal of Medicinal Chemistry 2004 47 (27) 6948-6957 is then added. The reaction mixture is stirred at room temperature overnight, diluted with dichloromethane (20 ml), washed with 1.5 N HCI (2 x 25 ml) and water (25 ml) and <n="20"/>finally dried over MgSO4 and evaporated to dryness, to give a yellowish solid. This crude material is purified by preparative HPLC (0.150 g, yield 31 %), to afford the title compound as white powder. LC-ESI-HRMS of [M+H]+ shows 408.0413 Da. CaIc. 408.042096 Da, dev. -2 ppm. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
2-(3-methanesulfonyl-phenyl)-ethanol was prepared as follows: To a solution of 3-methylsulphonylphenylacetic acid (200mg, 0.93mmol) in dry THF (3ml) at O0C was added borane-tetrahydrofuran complex ( 1.0M solution in THF, 1.4 equiv, 1.31 ml) dropwise. The reaction was allowed to warm up to room temperature overnight and then quenched with water. DCM/brine extraction gave 2-(3-methanesulfonyl-phenyl)-ethanol as a clear oil (184mg). | ||
160 mg | With borane-THF; In tetrahydrofuran; at 20℃; for 14.5h;Inert atmosphere; Cooling with ice; | Under a nitrogen atmosphere, borane-tetrahydrofuran complex (0.98 mol/L tetrahydrofuran solution, 1.91 mL) was added to a solution of commercially available <strong>[1877-64-1][3-(methanesulfonyl)phenyl]acetic acid</strong> (200 mg) in tetrahydrofuran (1.87 mL) under ice cooling, and the mixture was stirred at room temperature for 14.5 hours. The saturated sodium hydrogen carbonate was carefully added to the mixture to stop the reaction, and then the mixture was extracted with ethyl acetate three times. The combined organic layer was washed with water, and was separated by a phase separator, and the solvent was distilled off under reduced pressure. The obtained residue was purified by NH silica gel column chromatography (n-hexane/ethyl acetate = 4: 1, to ethyl acetate only) to give the title compound (160 mg) as a colorless oily substance. 1H NMR (600 MHz, CHLOROFORM-d) δ ppm 1.44 (t, J=5.6 Hz, 1 H) 2.97 (t, J=6.4 Hz, 2 H) 3.06 (s, 3 H) 3.89 - 3.96 (m, 2 H) 7.48 - 7.57 (m, 2 H) 7.77 - 7.87 (m, 2 H). MS ESI/APCI Multi posi: 223 [M+Na]+. MS ESI/APCI Multi nega: 235 [M+Cl]-. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With sulfuric acid; at 50℃; | Step 1: A solution of 3-methylsulfonylphenylacetic acid (1 g, 4.67 mmol) in methanol (25 mL) and few drops of concentrated H2SO4 was warmed at 50 C. overnight. The reaction mixture was concentrated in vacuo, dissolved in CH2Cl2, poured onto H2O and extracted 3 times with CH2Cl2. The organic phase was dried over Na2SO4 and concentrated in vacuo to afford (3-methanesulfonylphenyl)acetic acid methyl ester (1.04 g, 98%): 1H NMR (300 MHz, CHLOROFORM-d) δ ppm 3.07 (s, 3H) 3.73 (s, 3H) 3.74 (s, 2H) 7.51-7.64 (m, 2H) 7.82-7.92 (m, 2H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
0.035 g | With 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In dichloromethane; at 20℃; for 4.5h; | The compound obtained in Example 47e (0.052 g), in dichloromethane (2 mL), 2-[3-(methylsulfonyl)phenyl]acetic acid (0.027 g), triethylamine (0.035 mL), 1-[3-(dimethylamino)propyl]-N'-ethylcarbodiimide hydrochloride (0.037 g), 3H-1,2,3-triazolo[4,5-b]pyridin-3-ol (0.0086 g) was added and the mixture was stirred for 1 hour at room temperature for 30 minutes. The reaction mixture was added water mixed solvent of ethyl acetate and dichloromethane (4:1) After extraction, the organic layer was washed with saturated brine. The organic layer was dried over sodium sulfate and concentrated under reduced pressure, the residue was purified by column chromatography(ethyl acetate/hexane) to give the title compound (0.035 g) as a white amorphous solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine; 1-(methanesulfonyl)-1H-1,2,3-benzotriazole; In tetrahydrofuran; at 160℃; for 0.166667h;Microwave irradiation; Sealed tube; | General procedure: Compound 16 (216 mg, 1.0 mmol), phenylacetic acid (150 mg, 1.10 mmol) and N-(1-methanesulfonyl)benzotriazole (220 mg, 1.10 mmol) were placed in a microwave reaction vessel. TΗF (2 mL) was added followed by Et3N (0.5 mL, 3.59 mmol) and the mixture heated in the sealed tube at 160 C for 10 minutes. Upon cooling to RT the reaction was concentrated to l mL, and then MeCN was added (4mL) and the product 2-phenyl-N-[4-(1H-pyrrolo[2,3-b]pyridin-3-yl)-thiazol-2-yl]-acetamide precipitated, was filtered, washed with acetonitrile and dried. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99.0% | With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In dichloromethane; at 20℃; for 3.0h; | The method is the same as in example 1. 4'-Amino-2',6'-dichloro-4-isobutyl-[1,1'-biphenyl]-3-carbonitrile (50 mg, 0.16 mmol), <strong>[1877-64-1]2-(3-(methylsulfonyl)phenyl)acetic acid</strong> (41 mg, 0.19 mmol), HATU (72 mg, 0.19 mmol), N,N-diisopropylethylamine (62 mg, 0.48 mmol) and dichloromethane (3 mL) were reacted at room temperature for 3 hours. The crude product was separated by a silica gel column (petroleum ether: ethyl acetate =1:1-1:2) to give a product (white solid, 82 mg), with a yield of 99.0%. 1H NMR (400 MHz, CDCl3) δ 8.92 (s, 1H), 7.96 (s, 1H), 7.87 (d, J = 7.8 Hz, 1H), 7.75 - 7.65 (m, 3H), 7.56 (t, J = 7.7 Hz, 1H), 7.47 (s, 1H), 7.35 (s, 2H), 3.82 (s, 2H), 3.11 (s, 3H), 2.76 (d, J = 7.2 Hz, 2H), 2.15 - 1.97 (m, 1H), 0.99 (d, J = 6.5 Hz, 6H). MS (ESI) m/z: 512.8 (M-1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
19% | With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl acetamide; at 20℃; for 24.0h; | o a stirred solution of 2-(2-aminopyridin-4-yl)-3-anilino-5-methyl-1 ,5,6,7-tetrahydro-4H- pyrrolo[3,2-c]pyridin-4-one (see Intermediate 3, 120 mg, 360 pmol) in DMA (4.0 mL) was added N,N-diisopropylethylamine (380 mI, 2.2 mmol), <strong>[1877-64-1][3-(methanesulfonyl)phenyl]acetic acid</strong> (154 mg, 720 pmol) and PyBOP (937 mg, 1.80 mmol). The mixture was stirred at r.t. for 24 h. An aqueous solution of sodium bicarbonate was added, the mixture was stirred for 5 minutes and the mixture was extracted with ethyl acetate. The organic phase was washed with saturated sodium chloride solution, dried (sodium sulfate), filtered and the solvent was removed in vacuum. Silicagel chromatography followed by preparative reverse phase HPLC (gradient of water and acetonitrile containing ammonium hydroxide as additiv) gave a solid that was triturated with ethyl acetatene to give 40.7 mg (19 % yield) of the title compound.LC-MS (Method 2): Rt= 0.99 min; MS (ESIpos): m/z = 530 [M+H]+-NMR (400 MHz, DMSO-de) d [ppm]: 1.154 (2.90), 1.172 (5.84), 1.190 (2.76), 1.988 (10.34), 2.518 (1.37), 2.523 (0.95), 2.854 (11.93), 2.886 (1.16), 2.903 (2.50), 2.921 (1.24), 3.221 (16.00), 3.377 (0.61), 3.507 (1.40), 3.524 (2.87), 3.541 (1.28), 3.855 (4.66), 4.000 (0.76), 4.017 (2.29),4.035 (2.22), 4.053 (0.71), 6.539 (2.43), 6.558 (2.58), 6.560 (2.16), 6.594 (0.76), 6.612 (1.60),6.630 (0.88), 6.988 (1.95), 7.007 (2.41), 7.009 (2.43), 7.028 (1.54), 7.124 (1.54), 7.128 (1.44),7.137 (1.40), 7.142 (1.53), 7.353 (3.02), 7.606 (0.78), 7.625 (2.19), 7.644 (1.71), 7.667 (0.92),7.670 (1.65), 7.674 (1.10), 7.686 (0.57), 7.690 (0.82), 7.693 (0.48), 7.823 (0.86), 7.827 (1.31),7.831 (0.98), 7.842 (0.72), 7.847 (1.10), 7.850 (0.76), 7.930 (1.32), 7.934 (2.14), 7.938 (1.24),8.047 (1.93), 8.061 (1.88), 8.195 (1.67), 10.677 (2.25), 11.730 (1.59). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69% | With triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide; for 16.0h; | To a solution of <strong>[1877-64-1]2-(3-(methylsulfonyl)phenyl)acetic acid</strong> (0.039 g, 0.182 mmol) and methyl 3-(4-amino-2,6-dichlorophenoxy)-5-fluorobenzoate (0.030 g, 0.091 mmol) in DMF (0.606 ml) was added HATU (0.073 g, 0.191 mmol) and triethylamine (0.051 ml, 0.363 mmol). After 16 hours, the reaction was diluted with water and extracted three times with EtOAc. The organic layers were concentrated. The residue was purified via ISCO ( 24g column; Hex/EtOAc;0 to 100% gradient) to give methyl 3-(2,6-dichloro-4-(2- (3-(methylsulfonyl)phenyl)acetamido)phenoxy)-5-fluorobenzoate (0.033 g, 0.063 mmol, 69.0 % yield). LCMS m/z 526.1 (M+H); rt 1.01 min; Condition C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
18.8% | With benzotriazol-1-ol; N-[3-(N,N-dimethylamino)-propyl]-N'-ethyl-carbodiimide hydrochloride; triethylamine; In N,N-dimethyl-formamide; for 16.0h; | To a solution of N2-((1R,4R)-4-aminocyclohexyl)-N4-(5-cyclopropyl-1H- pyrazol-3-yl)-N2-methylpyrimidine-2,4-diamine (200 mg, 0.610 mmol) and 2-(3- (methylsulfonyl)phenyl)acetic acid (131 mg, 0.610 mmol) in dry DMF (3 mL) was added triethylamine (0.17 mL, 1.22 mmol) drop-wise followed by the addition of EDC.HCl (176 mg, 0.916 mmol) and HOBt (41 mg, 0.305 mmol). The reaction mixture was stirred for 16 h. After the completion of reaction, the reaction mixture was diluted with dichloromethane, washed with water and brine and dried over anhydrous Na2SO4 and concentrated to yield the crude product. The crude compound was purified by reverse phase preparative HPLC to obtain N-((1R,4R)-4-((4-((5-cyclopropyl-1H-pyrazol-3-yl)amino)pyrimidin-2- yl)(methyl)amino)cyclohexyl)-2-(3-(methylsulfonyl)phenyl) acetamide (60 mg, 18.8%) as the free base. LC purity: 99.65%; m/z: 524.3 [M+H]+ (Mol. formula C26H33N7O3S, calcd. mol. wt. 523.66).1H NMR (400MHz, DMSO-d6): δ 11.92 (s, 1H), 9.32 (s, 1H), 8.10 (d, J = 7.6 Hz, 1H), 7.85-7.78 (m, 3H), 7.59 (t, J= 7.6 Hz, 2H), 6.32-6.12 (m, 2H), 4.52-4.42 (m, 1H), 3.54 (s, 3H), 3.20 (s, 3H), 2.91 (s, 3H), 1.92-1.84 (m, 3H), 1.65-1.61 (m, 4H), 1.34 - 1.23 (m, 2H), 0.92-0.90 (m, 2H), 0.67-0.63 (m, 2H). |
Tags: 1877-64-1 synthesis path| 1877-64-1 SDS| 1877-64-1 COA| 1877-64-1 purity| 1877-64-1 application| 1877-64-1 NMR| 1877-64-1 COA| 1877-64-1 structure
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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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