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CAS No. : | 1857-19-8 | MDL No. : | MFCD06655264 |
Formula : | C4H10N2O | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | KNVRBEGQERGQRP-UHFFFAOYSA-N |
M.W : | 102.14 | Pubchem ID : | 4961823 |
Synonyms : |
|
Signal Word: | Danger | Class: | 8 |
Precautionary Statements: | P261-P264-P271-P280-P302+P352-P304+P340+P312-P305+P351+P338+P310-P332+P313-P362-P403+P233-P405-P501 | UN#: | 2735 |
Hazard Statements: | H314 | Packing Group: | Ⅲ |
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 |
---|---|---|
94% | With palladium 10% on activated carbon; hydrogen In methanol at 20℃; for 3 h; | General procedure: This procedure is illustrated for compound 11a. To a solution of compound 10a (170 mg, 0.77 mmol) in methanol (10 mL), 10percent Pd/C was added. The reaction was hydrogenated at room temperature and atmospheric pressure for 3 h. Then the catalyst was filtered off through Celite, and the clear solution, taken to dryness, afforded the title compound as an oil. The reaction was monitored by TLC and, for stability problems, the amine was directly used in the subsequent reaction. Yield 97percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | With palladium 10% on activated carbon; hydrogen; In methanol; at 20℃; under 760.051 Torr; for 3h; | General procedure: This procedure is illustrated for compound 11a. To a solution of compound 10a (170 mg, 0.77 mmol) in methanol (10 mL), 10percent Pd/C was added. The reaction was hydrogenated at room temperature and atmospheric pressure for 3 h. Then the catalyst was filtered off through Celite, and the clear solution, taken to dryness, afforded the title compound as an oil. The reaction was monitored by TLC and, for stability problems, the amine was directly used in the subsequent reaction. Yield 97percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine; In dichloromethane; | Step 1 N,N-dimethyl-2-[(methylsulfonyl)amino]acetamide To a cold (0° C.) solution of <strong>[1857-19-8]2-amino-N,N-dimethylacetamide</strong> (1.62 g, 10 mmol) and triethylamine (3.4 mL, 25 mmol) in dichloromethane (50 mL), methanesulfonyl chloride (0.85 mL, 11 mmol) was added over a period of 5 minutes. The resultant mixture was stirred at room temperature for overnight. The product mixture was diluted with dichloromethane and washed with sat. aq. sodium bicarbonate. The organic extract was dried over anhydrous magnesium sulfate, filtered and concentrated under vacuum to provide the title acetamide as white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In chloroform; water; | EXAMPLE A Preparation of N,N-dimethyl-2-[6-phenyl-2-(4-trifluoromethylphenyl)-4-pyrimidinylamino]acetamide: A mixture of 4-chloro-6-phenyl-2-(4-trifluoromethylphenyl)-pyrimidine (15 g), <strong>[1857-19-8]2-amino-N,N-dimethylacetamide</strong> (8.2 g) and triethyl-amine (5.4 g) is heated at 150° C. under reflux for 2 hours. To the reaction mixture are added water and chloroform, and the chloroform layer is separated, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue is purified by silica gel column chromatography (eluent: chloroform), and recrystallized from ethanol to give the desired compound (16 g). M.p. 178-179° C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
EXAMPLE 44 Preparation of [1S-[1alpha(betaS*,deltaS*),2alpha,4abeta,6beta,8beta,8aalpha]]-6-[[(Dimethylamino)acetyl]amino]-8-(2,2-dimethyl-1-oxobutoxy)decahydro-beta,delta-dihydroxy-2-methyl-1-naphthaleneheptanoic acid, monolithium salt STR103 A solution of the dimethyl amino acetamide prepared as the title product in step (b) of Example 43 above (150 mg, 0.295 mmol) was dissolved in CH3 CN/H2 O and treated with 1N LiOH (0.590 mmol, 590 mul) and was stirred for 2 hours. The acetonitrile was removed by evaporation and the residue was purified by column chromatography using CHP-20P as the stationary phase and | ||
(b) Glycine dimethylamide Obtained from the previous product (Example 78(a)) by a procedure similar to that described in Example 2, but using 10percent palladium on charcoal as catalyst, as an oil. Rf 0.21 (SS 7). LRMS: m/z 103.1 (M+1)+. HRMS: m/z 103.08710. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine; In tetrahydrofuran; at 20℃; for 1h; | To 7-(6-methoxypyridin-3-yl)-1 -(2-propoxyethyl)-1 ,4-dihydropyrido[2,3-b]pyrazine-2,3- dione (3.5 g, 9.8 mmol) in Lambda/,/V-dimethylformamide (76 DL, 1.0 mmol) and methylene chloride (98 ml_) was added oxalyl chloride (2.4 mL, 24.5 mmol) at room temperature and stirred for 1 hour. The solvent was removed in vacuo and the intermediate residue mixed with tetrahydrofuran (20 mL), triethylamine (6.8 mL, 48.8 mmol) and N~1 ~,N~1~- dimethylglycinamide (1.8 g, 10.8 mmol) at room temperature. The reaction mixture was stirred for 1 hour and the solvent was removed in vacuo. The crude material was partitioned between methylene chloride and water. The organic layer was washed with brine, dried over sodium sulfate, filtered, and concentrated in vacuo. The crude material was purified via Biotage column choromatography (gradient eluant of 2percent methanol/methylene chloride to 5percent methanol/methylene chloride) to afford 3.0 g of N~2~-[7-(6-methoxypyridin-3-yl)-2-oxo-1-(2- propoxyethyl)-1 ,2-dihydropyrido[2,3-b]pyrazin-3-yl]-N~1 ~,N~1 -dimethylglycinamide as a white solid. 1 H NMR (400 MHz, CHLOROFORM-D) delta ppm 0.72 (t, 3 H) 1.44 (m, 2 H) 3.03 (s, 3 H) 3.06 (s, 3 H) 3.32 (t, 2 H) 3.79 (t, 2 H) 3.98 (s, 3 H) 4.39 (d, 2 H) 4.47 (t, 2 H) 6.84 (d, 1 H) 7.63 (t, 1 H) 7.80 (dd, 1 H) 7.93 (d, 1 H) 8.40 (d, 1 H) 8.55 (d, 1 H). HRMS m/z 441.2231 (calculated for M+H, 441.2245). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
57.3% | General procedure: This procedure is illustrated for compound 12a. To a stirred solution of 9 (287 mg, 0.85 mmol) in dichloromethane at 0 °C, dicyclohexylcarbodiimide (DCC) (211 mg, 1.02 mmol, 1.2 equiv) and hydroxybenzotriazole (HOBt) (138 mg, 1.02 mmol, 1.2 equiv) were added. The reaction mixture was maintained at 0 °C for 1 h, and then it was allowed to warm up to room temperature. Compound 11a (130 mg, 1.27 mmol, 1.5 equiv) was added, and the reaction mixture was stirred for 12 h. The DCU was filtered, and the organic layer was washed with 5percent citric acid solution (2.x.), saturated aqueous sodium bicarbonate (2.x.), and brine, dried and concentrated in vacuo, to afford a clear oil. The obtained residue was purified by flash column chromatography (chloroform/methanol, 9:1), affording the title compound as a white solid. Yield 75.6percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1-Methyl-2-(6-trifluoromethoxy-benzothiazol-2-ylamino)-1H-benzoimidazole-5-carboxylic acid dimethylcarbamoylmethyl-amide may be prepared from 1-methyl-2-(6-trifluoromethoxy-benzothiazol-2-ylamino)-1H-benzimidazole-5-carboxylic acid, 2-amino-N,N-dimethyl-acetamide, 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (HBTU), and DIEA. To a solution of the carboxylic acid in dry DMF may be added DIEA followed by HBTU, and the reaction mixture stirred at room temperature for 30 min. The 2-amino-N,N-dimethyl-acetamide may then be added, and the reaction stirred at room temperature for 16 hours. The contents may be diluted with ice water, and the product precipitated. The product may be isolated after filtration either with subsequent washings with water and dichloromethane/methanol or through silica gel chromatography using hexanes/ethyl acetate (from 80:20 to 60:40) as an eluent system. LC/MS: m/z 494 [M+2]. 1H NMR (DMSO-d6, 400 MHz): delta 8.42 (t, 1H), 8.09 (s, 1H), 7.90 (m, 1H), 7.78 (br, 1H), 7.72 (br, 1H), 7.48 (d, 1H), 7.44 (d, 1H), 7.34 (m, 1H), 4.11 (d, 2H), 3.63 (s, 3H), and 3.00 (d, 6H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | Example 33 N-[2-(dimethylamino)-2-oxoethyl]-6-[5-(trifluoromethyl)pyridin-2-yl]oxy}quinoline-2-carboxamide The product from Example 1D (29.67 g, 89.00 mmol) was subjected to the conditions described in Example 2, substituting <strong>[1857-19-8]2-amino-N,N-dimethylacetamide</strong> for 3-aminotetrahydrothiophene 1,1-dioxide hydrochloride, to give the titled compound (22.20 g, 60percent). 1H NMR (400 MHz, DMSO-d6) delta ppm 8.95 (t, J=5.1 Hz, 1H), 8.68-8.50 (m, 2H), 8.32 (dd, J=8.7, 2.6 Hz, 1H), 8.21 (dd, J=8.8, 2.9 Hz, 2H), 7.95 (d, J=2.6 Hz, 1H), 7.78 (dd, J=9.1, 2.7 Hz, 1H), 7.41 (d, J=8.7 Hz, 1H), 4.25 (d, J=5.1 Hz, 2H), 3.04 (s, 3H), 2.91 (s, 3H); MS (ESI+) m/z 419.0 [M+H]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Example 108 N-[2-(Dimethylamino)-2-oxoethyl]-7-[(4-fluorophenyl)methyl]-4-hydroxy-1-methyl-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide The title compound was made in a manner similar to example 96 using <strong>[1857-19-8]N',N'-dimethylglycinamide</strong> to give an off-white solid: 1H NMR (CDCl3) delta 10.89 (1H, m), 8.58 (1H, s), 7.43 (1H, s), 7.16 (2H, m), 7.02 (2H, m), 4.26 (2H, d, J=5 Hz), 4.14 (2H, s), 3.59 (3H, s), 3.05 (3H, s), 3.03 (3H, s); HRMS calcd for C211421FN4O4+H+: 413.1625. Found: 413.1617. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
General procedure: The following compounds were prepared according to methods closely related to those exemplified for compound 25. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate; In acetonitrile; at -15 - 20℃; | 2-Amino-N,N-dimethylacetamide (51.1 mg, 0.500 mmol) was dissolved in acetonitrile (4 mL), and potassium carbonate (104 mg, 0.750 mmol) was added thereto, followed by cooling to ?10° C. to ?15° C. Then, benzyl 2-bromoacetate (0.086 mL, 0.550 mmol) diluted with acetonitrile (1 mL) was added dropwise, and the temperature was gradually raised to room temperature, followed by stirring overnight |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
8.23% | In dimethyl sulfoxide; at 120℃; for 24h; | A mixture of N-(5-(4-cyano-3-fluorophenyl)pyrazin-2-yl)-2- methylcyclopropanecarboxamide (51.4 mg, 0.173 mmol) and <strong>[1857-19-8]2-amino-N,N-dimethylacetamide</strong> (267 mu, 2.60 mmol were combined in anhydrous DMSO (1000 mu) and heated at 120°C for 24 hours. Reaction volume was then doubled in MeOH and purified by preparative HPLC (SunfireTM CI 8, 5muMu, ID TFA) using a gradient of 35-60percent ACN (with 0.035percent TFA) in water (with 0.05percent TFA). The pure fractions were combined and concentrated in vacuo to afford the title compound as a yellow oil (5.4 mg, 8.23percent). 1H NMR (400 MHz, methanol-d4) delta ppm 0.78 (ddd, J=7.89, 6.38, 3.92 Hz, 1 H) 1.16 - 1.26 (m, 4 H) 1.39 - 1.47 (m, 1 H) 1.66 (dt, J=8.02, 4.20 Hz, 1 H) 2.98 - 3.03 (m, 4 H) 3.10 - 3.15 (m, 3 H) 4.16 - 4.21 (m, 2 H) 7.33 - 7.39 (m, 2 H) 7.54 (d, J=7.83 Hz, 1 H) 8.87 (s, 1 H) 9.39 - 9.45 (m, 1 H); ESI-MS m/z [M+H]+ 379.0. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium cyanoborohydride; acetic acid; In methanol; at 0 - 20℃; for 3h; | To a mixture of <strong>[1857-19-8]2-amino-N,N-dimethylacetamide</strong> (2.01 g, 19.71 mmol) in MeOH (10 mL) at 0 C. was added NaBH3CN (1.24 g, 19.71 mmol), AcOH (1.13 mL, 19.71 mmol), then tert-butyl 7-(4-oxobutyl)-3,4-dihydro-1,8-naphthyridine-1(2H)-carboxylate (3 g, 9.86 mmol) and the resulting mixture was stirred at rt for 3 h. The reaction mixture was then poured into sat. aq. NaHCO3 and then concentrated in vacuo to remove volatiles. The remaining aqueous layer was extracted with EtOAc and the combined organic extracts were dried over Na2SO4, filtered, and concentrated in vacuo. The crude residue was purified by normal phase silica gel chromatography to give the title compound. LCMS (ESI+): m/z=391.0 (M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
56% | General procedure: To a solutionof the corresponding aldehyde (1.2 eq.; unless stated otherwise) in DMF (2 inL per 0.3 mmol of aldehyde; unless stated otherwise) was added the corresponding amine (2.5 eq.; unless stated otherwise) and the resulting solution was stirred at 25 C to form the corresponding inline. Then, the corresponding isocyano(tosyl)methyl)arene reagent (1 eq.; unless stated otherwise) and K2CO3 (1.5 eq.; unless stated otherwise*) were added and the reaction mixture was stirred at 25 C (unless stated otherwise). The reaction was stopped after the time indicated for each particular reaction. The reaction progress was monitored by TLC. (0083) A saturated aqueous solution of NH4CI (10 mL per 1 mmol of aldehyde) was added to the reaction mixture, which was then extracted with EtOAc (2 x 30 mL per 1 mmol of aldehyde). The combined organic extracts were washed with H2O (2 x 25 mL per 1 mmol of aldehyde), dried over MgSCC, filtered, and the solvent was evaporated in vacuo to provide the crude product. The residue obtained after the workup was purified using column chromatography or preparative TLC (unless stated otherwise). (0084) * note: in cases when the amine was used as HC1 salt, 4 eq. of K2CO3 were used |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
59% | Stage #1: N',N'-dimethylglycinamide; 3-n-butoxyphenylacetaldehyde With acetic acid In tetrahydrofuran for 0.0833333h; Stage #2: With sodium tris(acetoxy)borohydride In tetrahydrofuran for 2.5h; | 5 Synthesis of 2-[2-(3-butoxyphenyl)-ethylamino]-N,N-dimethylacetamide 3 -but oxyphenyl acetaldehyde 1.95 g (1 equiv.) and 2-amino-N,N- dimethylacetamide 5.18 g (5 equiv.) were dissolved in anhydrous THF 340 mL. To this reaction mixture acetic acid 3.47 mL (6 equiv.) was added drop wise and the resulting solution was stirred for 5 minutes. To this solution STAB-H 8.6 g (4 equiv.) was added in portions and stirred for 2.5 hours. After the reaction was complete, Na2CO3 aqueous solution was added and the organic layer was separated. The aqueous layer was extracted twice with DCM 200 mL. The organic layers were combined, dried and concentrated. A flash column chromatography performed on crude material (8% ethyl acetate in heptanes) yielded 1.66 g (59% molar yield of 2-[2-(3-butoxyphenyl)-ethylamino]-N,N- dimethylacetamide free base). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
300 mg | With triethylamine In tetrahydrofuran at 25℃; for 12h; | Intermediate 5: N,N-dimethyl-2-(2-methyl-5-nitrophenylsulfonamido)acetamide [00519] To a solution of 2-methyl-5-nitrobenzene-1-sulfonyl chloride (CAS 121-02-8, 400 mg, 1.70 mmol) in THF (5 mL) was added triethylamine (343.53 mg, 3.39 mmol, 472.54 uL) and 2-amino-N,N-dimethyl-acetamide (CAS 1857-19-8, 208.05 mg, 2.04 mmol). The mixture was stirred at 25 °C for 12 hours. The was diluted with water (30 mL) and extracted with ethyl acetate (30 mL, two times). The combined organic layers were washed with saturated sodium chloride aqueous solution (40mL), dried over sodium sulfate, insoluble materials were removed by filtration, volatiles removed under reduced pressure, and the residue was used as the title compound without further manipulation as a yellow oil (300 mg) as a yellow oil. [00520] LCMS (ESI): Rt=0.792min, [M+H]+=302.0 |
300 mg | With triethylamine In tetrahydrofuran at 25℃; for 12h; | Intermediate 5: N,N-dimethyl-2-(2-methyl-5-nitrophenylsulfonamido)acetamide [00519] To a solution of 2-methyl-5-nitrobenzene-1-sulfonyl chloride (CAS 121-02-8, 400 mg, 1.70 mmol) in THF (5 mL) was added triethylamine (343.53 mg, 3.39 mmol, 472.54 uL) and 2-amino-N,N-dimethyl-acetamide (CAS 1857-19-8, 208.05 mg, 2.04 mmol). The mixture was stirred at 25 °C for 12 hours. The was diluted with water (30 mL) and extracted with ethyl acetate (30 mL, two times). The combined organic layers were washed with saturated sodium chloride aqueous solution (40mL), dried over sodium sulfate, insoluble materials were removed by filtration, volatiles removed under reduced pressure, and the residue was used as the title compound without further manipulation as a yellow oil (300 mg) as a yellow oil. [00520] LCMS (ESI): Rt=0.792min, [M+H]+=302.0 |
Tags: 1857-19-8 synthesis path| 1857-19-8 SDS| 1857-19-8 COA| 1857-19-8 purity| 1857-19-8 application| 1857-19-8 NMR| 1857-19-8 COA| 1857-19-8 structure
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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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