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CAS No. : | 69687-80-5 | MDL No. : | MFCD00203859 |
Formula : | C8H11NO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 153.18 | Pubchem ID : | - |
Synonyms : |
|
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 |
---|---|---|
92% | With pyridinium hydrobromide perbromide; triethylamine In dichloromethane at 0℃; for 2 h; | To a mixture of methyl 2,5-dimethyl-1H-pyrrole-3-carboxylate 21 (6.85 g, 45.0 mmol), triethylamine (8.7 mL, 63.0 mmol) and CH2Cl2 (270 mL) was added pyridinium bromide perbromide (15.7 g, 15.7 mmol) portionwise at 0 °C. After stirring at 0 °C for 2 h, the mixture was poured into brine and extracted with EtOAc. The organic layer was dried over anhydrous MgSO4 and concentrated in vacuo. The residue was purified by silica gel column chromatography (hexane-EtOAc). The product was recrystallized from hexane-EtOAc to give 22 (7.59 g, 92percent) as yellow crystals. 1H NMR (300 MHz, CDCl3) δ: 2.19 (3H, s), 2.47 (3H, s), 3.82 (3H, s), 8.20 (1H, s). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride; diethyl ether; hydrogen cyanide Hydrolysieren des Reaktionsprodukts; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
20% | With ammonium hydroxide at 20℃; for 17h; | |
With ammonium hydroxide at -1℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With aluminium trichloride 1.) CH2Cl2, room temperature, 15 min, 2.) room temperature, 10 min; Yield given. Multistep reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
46% | In dichloromethane at 20℃; for 5h; | |
In dichloromethane | 2.a a) a) Methyl 4-(2-Iodobenzoyl)-2,5-dimethyl-1H-pyrrole -3-carboxylate Aluminium chloride (12g) was added to a stirred solution at -70° of methyl 2,5-dimethyl-1H-pyrrole -3-carboxylate (9.18g, 60mmol) and 2-iodobenzoyl chloride (16g, 60mmol) in dichloromethane (150ml). The reaction mixture was allowed to reach room temperature, stirred overnight and then poured onto ice. After dilution with chloroform, the organic layer was separated and washed with water, saturated sodium bicarbonate (twice) and brine, dried (Na2SO4) and the solvent evaporated. Crystallisation from toluene gave the sub-title compound (6.6g), mp 125-126°. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With aluminium trichloride In dichloromethane for 16h; Ambient temperature; Yield given; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
32% | With aluminium trichloride In dichloromethane at 20℃; for 2h; 1.) CH2Cl2, -78 deg C, 2.) CH2Cl2, 20 deg C, 2 h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | With aluminium trichloride In dichloromethane at 20℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | In dichloromethane at 20℃; for 2h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69% | In dichloromethane at 20℃; for 24h; 1.) CH2Cl2, -78 deg C, 2.) CH2Cl2, 20 deg C, 24 h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With aluminium trichloride In dichloromethane Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | In dichloromethane at 20℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61% | In dichloromethane at 20℃; for 3h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With aluminium trichloride In dichloromethane Ambient temperature; | |
73% | In dichloromethane at 0℃; for 0.5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | With aluminium trichloride In dichloromethane Ambient temperature; | |
41% | In dichloromethane at 20℃; for 4h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | With aluminium trichloride In dichloromethane Ambient temperature; | |
22% | In dichloromethane at 20℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
37% | In dichloromethane at 20℃; for 2h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
66% | In dichloromethane at 20℃; for 48h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
15% | In dichloromethane at -60℃; for 0.0833333h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
9% | In dichloromethane at -30℃; for 0.166667h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
30% | In dichloromethane at -10℃; for 0.666667h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With aluminium trichloride 1.) CH2Cl2, room temperature, 15 min, 2.) room temperature, 10 min; Yield given. Multistep reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With pyridinium hydrobromide perbromide; triethylamine; In dichloromethane; at 0℃; for 2h; | To a mixture of methyl 2,5-dimethyl-1H-pyrrole-3-carboxylate 21 (6.85 g, 45.0 mmol), triethylamine (8.7 mL, 63.0 mmol) and CH2Cl2 (270 mL) was added pyridinium bromide perbromide (15.7 g, 15.7 mmol) portionwise at 0 C. After stirring at 0 C for 2 h, the mixture was poured into brine and extracted with EtOAc. The organic layer was dried over anhydrous MgSO4 and concentrated in vacuo. The residue was purified by silica gel column chromatography (hexane-EtOAc). The product was recrystallized from hexane-EtOAc to give 22 (7.59 g, 92%) as yellow crystals. 1H NMR (300 MHz, CDCl3) delta: 2.19 (3H, s), 2.47 (3H, s), 3.82 (3H, s), 8.20 (1H, s). |
With pyridine perbromohydrobromide; triethylamine; In dichloromethane; at 0℃; for 2h; | 4-bromo-2,5-dimethyl-1H-pyrrole-3-carboxylate To a solution of methyl 2,5-dimethyl-1H-pyrrole-3-carboxylate (6.85 g) and triethylamine (8.7 ml) in dichloromethane (270 ml) was added pyridine perbromohydrobromide (15.7 g) little by little at 0 C. The reaction mixture was stirred at the same temperature for 2 hours and poured into saturated sodium chloride solution.. The reaction mixture was extracted with ethyl acetate, and the ethyl acetate layer was dried over magnesium sulfate and concentrated.. The residue was purified by column chromatography (carrier: silicagel, eluant: hexane-ethyl acetate) and recrystallized from ethyl acetate-hexane to obtain the titled compound (7.59 g) as yellow crystals.1H-NMR (CDCl3) delta 2.19 (3H, s), 2.47 (3H, s), 3.82 (3H, s), 8.20 (1H, s). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
57% | With tetrakis(triphenylphosphine) palladium(0); 2,4,6-trimethylphenyl bromide; potassium carbonate In N,N-dimethyl-formamide at 150℃; for 3.5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
19% | With iron(III) chloride In chloroform; water; acetic acid |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
44% | With iron(III) chloride In chloroform; water; acetic acid |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
31% | In acetic acid at 20℃; for 2h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | With toluene-4-sulfonic acid In ethanol for 3h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
39% | In acetic acid at 20℃; for 2h; | |
39% | In chloroform; water; acetic acid | 14 Example 14 Example 14 Preparation of Methyl 4-(1,4-Dioxo-1,4-dihydronaphthalen-2-yl)-2,5-dimethyl-1H-pyrrole-3-carboxylate STR23 40 millimol of 1,4-naphthoquinone and 10 millimol of methyl 3-(2,5-dimethyl-1H-pyrrolyl)carboxylate were stirred in 50 ml of glacial acetic acid in a round-bottomed flask for 2 hours at room temperature. The reaction mixture was diluted with 300 ml of chloroform and the resulting mixture was then poured into a large volume of water (300 ml). The organic phase was then separated out and washed four times with 100 ml of water and finally with saturated aqueous NaCl solution. The resulting organic phase was dried over Na2 SO4 and then concentrated under vacuum. The methyl 4-(1,4-dioxo-1,4-dihydronaphthalen-2-yl)-2,5-dimethyl-1H-pyrrole-3-carboxylate was thus isolated in a yield of a 39% after purification by chromatography on a column of silica. 1 H NMR 200 MHz (DMSO-d6, δ ppm): 2.17 (s, 3H), 2.38 (s, 3H), 3.44 (s, 3H), 6.77 (s, 1H), 7.85 to 7.91 (m, 2H), 7.97 to 8.04 (m, 2H), 11.44 (broad s, 1H). Melting point: 209-210° C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: AlCl3 / CH2Cl2 / 0.42 h 2: AlCl3 / 0.25 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: AlCl3 / CH2Cl2 / 0.42 h 2: AlCl3 / 0.25 h 3: 4500 mmol / tritium (gas), Et3N / 10percent Pd/C / tetrahydrofuran / 1 h / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: 80 percent / pyridinium hydrobromide perbromide, triethylamine / CHCl3 / 0 °C 2: 1.) NaH / 1.) THF, 0 deg C, 45 min, 2.) THF, RT, 2 h 3: 1.) n-BuLi / 1.) hexane, THF, -78 deg C, 15 min, 2.) hexane, THF, from -78 deg C to RT 4: 1.) boron trifluoride etherate, 2.) Triton B / 1.) CH2Cl2, RT, 2 h, 2.) acetonitrile, methanol |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 80 percent / pyridinium hydrobromide perbromide, triethylamine / CHCl3 / 0 °C 2: 1.) NaH / 1.) THF, 0 deg C, 45 min, 2.) THF, RT, 2 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: AlCl3 / CH2Cl2 / 1 h 2: AlCl3 / CH2Cl2 / 2 h | ||
Multi-step reaction with 2 steps 1: AlCl3 / CH2Cl2 / 1 h 2: AlCl3 / CH2Cl2 / 2 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: AlCl3 / CH2Cl2 / 1 h 2: AlCl3 / CH2Cl2 / 2 h | ||
Multi-step reaction with 2 steps 1: AlCl3 / CH2Cl2 / 1 h 2: AlCl3 / CH2Cl2 / 2 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 80 percent / pyridinium hydrobromide perbromide, triethylamine / CHCl3 / 0 °C 2: 1.) NaH / 1.) THF, 0 deg C, 45 min, 2.) THF, RT, 2 h 3: 1.) n-BuLi / 1.) hexane, THF, -78 deg C, 15 min, 2.) hexane, THF, from -78 deg C to RT |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: AlCl3 / CH2Cl2 / 16 h / Ambient temperature 2: 46 percent / (CH3CN)2PdCl2 / hexamethylphosphoric acid triamide / 110 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: AlCl3 / CH2Cl2 / 16 h / Ambient temperature 2: 49 percent / (CH3CN)2PdCl2 / hexamethylphosphoric acid triamide / 16 h / 110 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: aqueous NaOH 2: diethyl ether |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1 1.14 Methyl 2,5-Dimethyl-4-(2-((2-((phenylmethyl)thio) benzoyl)thio)benzoyl)-1H-pyrrole-3-carboxylate 1.14 Methyl 2,5-Dimethyl-4-(2-((2-((phenylmethyl)thio) benzoyl)thio)benzoyl)-1H-pyrrole-3-carboxylate Obtained as a by-product from the reaction of 2-((phenylmethyl)thio)benzoyl chloride with methyl 2,5-dimethyl-1H-pyrrole-3-carboxylate, mp 115°. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With thionyl chloride In dichloromethane; chloroform | 1 1.1 Methyl 2,5-Dimethyl-4-(2-((4-nitrophenyl)thio) benzoyl)-1H-pyrrole-3-carboxylate Example 1 1.1 Methyl 2,5-Dimethyl-4-(2-((4-nitrophenyl)thio) benzoyl)-1H-pyrrole-3-carboxylate 2-((4-Nitrophenyl)thio)benzoic acid (5.5g, 20mmol) and thionyl chloride (5.5ml) in chloroform (50ml) were heated at reflux for 4 hours. The solvent was evaporated and the residue azeotroped with toluene to remove excess thionyl chloride. The acid chloride was dissolved in dichloromethane (50ml) and methyl 2,5-dimethyl-1H-pyrrole-3-carboxylate (3.06g, 20mmol) in dichloromethane (100ml) was added. The mixture was cooled to -70° and, with stirring, aluminium chloride (4g) was added. After stirring at room temperature for 16 hours, the reaction mixture was poured onto ice/water/chloroform with stirring. After 2 hours, the solid was filtered off, washed with water, methanol and dichloromethane and dried in vacuo to give the title compound (5g). A microanalytically pure sample was prepared by crystallisation from dichloromethane/methanol, mp 224-225°. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrazine hydrate In Triethyl orthoacetate | 1.a a) a) 2-(2,5-Dimethyl-1H-Pyrrol-3-yl)-5-methyl-1,3,4-oxadiazole Methyl 2,5-dimethyl-1H-pyrrole-3-carboxylate (7.5g, 50mmol) and hydrazine hydrate (10ml) were heated at 120° for 16 hours. The reaction mixture was filtered off and the filtrate evaporated to dryness. The residue was crystallized from ethanol/water and the solid was filtered off. The combined solids were dried in vacuo and then heated at reflux under nitrogen in triethyl orthoacetate (25ml) for 24 hours. On cooling the sub-title oxadizole crystallized out and was filtered off (5.5g). M/e 177; nmr (D6DMSO) delta 2.15(s,3H), 2.42 (s,3H), 2.47 (s,3H), 6.04 (s,1H) and 11.04(s,1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With iodine; triethylamine In dichloromethane | 7.a a) a) Methyl 4-iodo-2,5-dimethyl-1H-pyrrole-3-carboxylate Iodine (13.2g,5.2mmol) was added to a stirred solution at -40° of methyl 2,5-dimethyl-1H-pyrrole-3-carboxylate (8g,5.2mmol) and triethylamine (5.8g,57.5mmol) in dichloromethane (250ml). After 10 hours at room temperature, the solvent was evaporated and the residue was chromatographed on silica eluding with ethyl acetate/dichloromethane mixtures to give the sub-title iodo compound (7.7g). M+ 279; nmr delta (CDCl3) 3.82(s,3H), 2.49(s,3H) and 2.20(s,3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With thionyl chloride; nitric acid In dichloromethane; chloroform | 1.ii ii) ii) Methyl 2,5-Dimethyl-4-(2-((2-nitrophenyl)methyl) benzoyl)-1H-pyrrole-3-carboxylate 2-(Phenylmethyl)benzoic acid (5g, 2.35mmol) was added with stirring to nitric acid (75ml, d=1.42) at room temperature. After 4 hours, the reaction mixture was poured onto ice/water with stirring. The solid was filtered off, washed with water and then dissolved in ether. The ethereal solution was washed with brine, dried (Na2SO4) and the solvent evaporated to give a mixture of the 2-- and 4--nitro acids. Chloroform (30ml) and thionyl chloride (5ml) were added and the mixture was heated at reflux for 4 hours. The solvent was evaporated and excess thionyl chloride removed by azeotroping with toluene. Methyl 2,5-dimethyl-1H-pyrrole-3-carboxylate (3.6g, 2.35mmol) in dichloromethane (100ml) was added and the mixture cooled with stirring to -70°. Aluminium chloride (4g) was added and the reaction mixture was allowed to reach room temperature overnight. After heating at reflux for 1 hour, the cooled reaction mixture was poured onto ice/water. The organic layer was separated and washed with water, saturated sodium bicarbonate and brine. After drying (Na2SO4), the solvent was evaporated. HPLC on silica eluding with ethyl acetate/petroleum ether bp 60-80° followed by recrystallisation three times from toluene gave the 4-nitrophenyl isomer (1.0g), mp 187-188°. The 2-nitrophenyl isomer was obtained from the first recrystallisation liquors by reverse phase HPLC eluding with methanol/water mixtures. Crystallisation from dichloromethane/cyclohexane gave the 2-nitrophenyl isomer (0.28g), mp 147-148°. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In dichloromethane | 1 1.3 Methyl 2,5-Dimethyl-4-(2-(2-phenylethyl)benzoyl)-1H-pyrrole-3-carboxylate 1.3 Methyl 2,5-Dimethyl-4-(2-(2-phenylethyl)benzoyl)-1H-pyrrole-3-carboxylate Aluminium chloride (4g) was added to a stirred solution at -78° of methyl 2,5-dimethyl-1H-pyrrole -3-carboxylate (2g, 13mmol) and 2-(2-phenylethyl)benzoyl chloride (3.5g, 14mmol) in dichloromethane (170ml). The reaction was allowed to warm to -30°, stirred at this temperature for 3 hours, then poured onto ice. After dilution with chloroform, the organic layer was separated, dried (MgSO4 and evaporated. Chromatography on silica eluding with ethyl acetate-hexane mixtures gave the title compound (2.1g) as a white solid, mp 42-48°. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In chloroform; | a) Methyl 4-Bromo-2,5-dimethyl-1H-pyrrole-3-carboxylate A stirred solution of methyl 2,5-dimethyl-1H-pyrrole -3-carboxylate (1.5g, 9.8mmol) in chloroform (60ml) and triethylamine (2.5ml) cooled to 0C was treated portionwise with pyridinium perbromide (3.5g, 10.94 mmol). The mixture was allowed to warm to room temperature and then silica (6g) was added in one portion and the entire mixture evaporated to dryness under reduced pressure (14 mm Hg) with gentle heating (below 50). Chromatography on silica eluding with ethyl acetate-hexane mixtures gave the sub-title compound (1.9g), M+231/233. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
2.11 g | In acetonitrile at 20℃; for 9h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: methyl 2,5-dimethyl-1H-pyrrole-3-carboxylate With aluminum (III) chloride In DCM at 0℃; for 0.166667h; Stage #2: 2-(3-bromophenyl)acetyl chloride In dichloromethane at 0 - 20℃; | 25.b (b) Methyl 4-(2-(3-bromophenyl)acetyl)-2,5-dimethyl-1H-pyrrole-3-carboxylate (49) A solution of methyl 2,5-dimethyl-1H-pyrrole-3-carboxylate (0.295 g, 1.93 mmol) in anhydrous DCM (5 mL) was added dropwise to a stirred suspension of aluminum trichloride (0.714 g, 5.35 mmol) in anhydrous DCM (10 mL) at 0° C., under nitrogen. The resulting suspension was stirred at 0° C. for 10 minutes. A solution of 2-(3-bromophenyl)acetyl chloride (48) (0.500 g, 2.14 mmol) in anhydrous DCM (5 mL) was added dropwise to the stirred suspension at 0° C. The resulting suspension was allowed to warm to room temperature and then stirred at room temperature for a further 18 hours. The reaction mixture was poured onto ice (50 mL) and conc HCl (2 mL). The layers were separated and the aqueous layer extracted with DCM (2*50 mL). The combined organics were washed sequentially with 2M HCl (2*75 mL), water (50 mL), and saturated NaHCO3 (50 mL). The organic layer was dried over Na2SO4, filtered and evaporated to afford crude product, which was used directly in the next stage; m/z (LC-MS, ESI-), RT=2.46 min (M-H=350.00). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | Stage #1: methyl 2,5-dimethyl-1H-pyrrole-3-carboxylate With aluminum (III) chloride In DCM at 0℃; for 0.166667h; Stage #2: 2-(3-(4-ethoxypiperidine-1-carbonyl)-4-fluorophenyl)acetic acid chloride In dichloromethane at 0 - 20℃; | 26.a (a) methyl 4-(2-(3-(4-ethoxypiperidine-1-carbonyl)-4-fluorophenyl)acetyl)-2,5-dimethyl-1H-pyrrole-3-carboxylate (53) A solution of methyl 2,5-dimethyl-1H-pyrrole-3-carboxylate (0.545 g, 3.56 mmol) in anhydrous DCM (10 mL) was added dropwise to a stirred suspension of aluminum trichloride (1.078 g, 8.08 mmol) in anhydrous DCM (20 mL) at 0° C., under nitrogen. The resulting suspension was stirred at 0° C. for 10 minutes. A solution of the requisite acid chloride [prepared earlier; by stirring 1-chloro-N,N,2-trimethylprop-1-en-1-amine (0.428 mL, 3.23 mmol) was added to a solution of 2-(3-(4-ethoxypiperidine-1-carbonyl)-4-fluorophenyl)acetic acid (1.000 g, 3.23 mmol) in anhydrous DCM (10 mL) at 0° C. and stirred for 2 hours] was added dropwise to the stirred suspension at 0° C. The resulting suspension was allowed to warm to room temperature and then stirred at room temperature for a further 18 hours. The reaction was incomplete and further aluminum trichloride (1.078 g, 8.08 mmol) was added and the solution was stirred at room temperature for a further 1 hour. The reaction mixture was poured onto ice (100 mL) and concentrated HCl (5 mL). The layers were separated and the aqueous layer extracted with DCM (2*100 mL). The combined organics were washed sequentially with 2M HCl (2*150 mL), water (100 mL), and saturated NaHCO3 (100 mL). The organic layer was dried over Na2SO4, filtered and evaporated to afford crude product. The crude product was purified by flash silica chromatography, elution gradient 0 to 100% ethyl acetate in isohexane. Pure fractions were evaporated to dryness to afford the desired material as a beige solid (1.241 g, 86% yield); 1H NMR (400.132 MHz, CDCl3) δ 1.14 (3H, t), 1.42-1.66 (2H, m), 1.71 (1H, m), 1.85 (1H, m), 2.00 (3H, s), 2.32 (3H, s), 3.06 (1H, m), 3.39-3.52 (5H, m), 3.75 (3H, s), 3.93-4.02 (3H, m), 6.92 (1H, t), 7.07 (1H, m), 7.17 (1H, m), 8.43 (1H, s); m/z (LC-MS, ESI+), RT=2.02 min (M+H=445.24). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | Stage #1: methyl 2,5-dimethyl-1H-pyrrole-3-carboxylate With aluminum (III) chloride In dichloromethane at 0℃; for 0.166667h; Stage #2: 2-(4-fluoro-3-(4-methoxypiperidine-1-carbonyl)phenyl)acetic acid chloride In dichloromethane at 0 - 20℃; | 27.a (a) Methyl 4-(2-(4-fluoro-3-(4-methoxypiperidine-1-carbonyl)phenyl)acetyl)-2,5-dimethyl-1H-pyrrole-3-carboxylate (57) A solution of methyl 2,5-dimethyl-1H-pyrrole-3-carboxylate (0.114 g, 0.74 mmol) in anhydrous DCM (5 mL) was added dropwise to a stirred suspension of aluminum trichloride (0.226 g, 1.69 mmol) in anhydrous DCM (10 mL) at 0° C., under nitrogen. The resulting suspension was stirred at 0° C. for 10 minutes. A solution of the requisite acid chloride [prepared earlier; 1-chloro-N,N,2-trimethylprop-1-en-1-amine (0.090 mL, 0.68 mmol) was added to a solution of 2-(4-fluoro-3-(4-methoxypiperidine-1-carbonyl)phenyl)acetic acid (43) (0.200 g, 0.68 mmol) in anhydrous DCM (5 mL) at 0° C. and stirred for 2 hours] was added dropwise to the stirred suspension at 0° C. The resulting suspension was allowed to warm to room temperature and then stirred at room temperature for a further 18 hours. The reaction was incomplete and further aluminum trichloride (0.226 g, 1.69 mmol) was added and the solution was stirred at room temperature for a further 1 hour. The reaction mixture was poured onto ice (50 mL) and conc HCl (2 mL). The layers were separated and the aqueous layer extracted with DCM (2*50 mL). The combined organics were washed sequentially with 2M HCl (2*75 mL), water (50 mL), and saturated NaHCO3 (50 mL). The organic layer was dried over Na2SO4, filtered and evaporated to afford crude product. The crude product was purified by flash silica chromatography, elution gradient 0 to 100% EtOAc in isohexane. Pure fractions were evaporated to dryness to afford methyl 4-(2-(4-fluoro-3-(4-methoxypiperidine-1-carbonyl)phenyl)acetyl)-2,5-dimethyl-1H-pyrrole-3-carboxylate (0.223 g, 76% yield) as a cream solid. 1H NMR (400.132 MHz, CDCl3) δ 1.57-1.90 (4H, m), 1.98 (3H, s), 2.31 (3H, s), 3.07 (1H, m), 3.29 (3H, s), 3.36-3.55 (3H, m), 3.75 (3H, s), 3.92 (1H, m), 3.97 (2H, s), 6.93 (1H, t), 7.07 (1H, m), 7.17 (1H, m), 8.50 (1H, s); m/z (LC-MS, ESI+), RT=1.89 min (M+H=431.19). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium tetrahydroborate; bis(1,5-cyclooctadiene)diiridium(I) dichloride; silver trifluoromethanesulfonate; 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran at 25 - 75℃; for 21h; Inert atmosphere; regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 1 - 20 °C / Inert atmosphere 1.2: 12 h / 20 °C / Inert atmosphere 2.1: acetic acid / 6 h / 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 1 - 20 °C / Inert atmosphere 1.2: 12 h / 20 °C / Inert atmosphere 2.1: acetic acid / 6 h / 20 °C / Inert atmosphere 3.1: acetic acid; platinum(II) chloride / 48 h / 80 °C / Inert atmosphere | ||
Multi-step reaction with 2 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 1 - 20 °C / Inert atmosphere 1.2: 12 h / 20 °C / Inert atmosphere 2.1: palladium diacetate; acetic acid / 1 h / 100 °C / Inert atmosphere | ||
Multi-step reaction with 3 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 1 - 20 °C / Inert atmosphere 1.2: 12 h / 20 °C / Inert atmosphere 2.1: acetic acid / 6 h / 20 °C / Inert atmosphere 3.1: palladium diacetate; acetic acid / 18 h / 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 1 - 20 °C / Inert atmosphere 1.2: 12 h / 20 °C / Inert atmosphere 2.1: acetic acid / 6 h / 20 °C / Inert atmosphere 3.1: palladium diacetate; acetic acid / 24 h / 100 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | Stage #1: methyl 2,5-dimethyl-1H-pyrrole-3-carboxylate With sodium hydride In N,N-dimethyl-formamide at 1 - 20℃; for 1h; Inert atmosphere; Stage #2: 1-Bromo-2-bromomethyl-benzene In N,N-dimethyl-formamide at 20℃; for 12h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: pyridinium hydrobromide perbromide; triethylamine / dichloromethane / 2 h / 0 °C 2.1: sodium hydride / tetrahydrofuran; mineral oil / 1 h / 0 °C 2.2: 3 h / 0 °C 3.1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / 1,2-dimethoxyethane; water / 1 h / 130 °C / Microwave irradiation |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: pyridinium hydrobromide perbromide; triethylamine / dichloromethane / 2 h / 0 °C 2.1: sodium hydride / tetrahydrofuran; mineral oil / 1 h / 0 °C 2.2: 3 h / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: pyridinium hydrobromide perbromide; triethylamine / dichloromethane / 2 h / 0 °C 2: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / water; N,N-dimethyl-formamide / 2 h / 130 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: pyridinium hydrobromide perbromide; triethylamine / dichloromethane / 2 h / 0 °C 2.1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / water; N,N-dimethyl-formamide / 2 h / 130 °C / Inert atmosphere 3.1: boron tribromide / dichloromethane / 1 h / 0 °C 3.2: brine |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: pyridinium hydrobromide perbromide; triethylamine / dichloromethane / 2 h / 0 °C 2.1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / water; N,N-dimethyl-formamide / 2 h / 130 °C / Inert atmosphere 3.1: boron tribromide / dichloromethane / 1 h / 0 °C 3.2: brine 4.1: thionyl chloride / tetrahydrofuran / 1 h / 20 °C 5.1: ammonium hydroxide / tetrahydrofuran / 1 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: pyridinium hydrobromide perbromide; triethylamine / dichloromethane / 2 h / 0 °C 2.1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / water; N,N-dimethyl-formamide / 2 h / 130 °C / Inert atmosphere 3.1: boron tribromide / dichloromethane / 1 h / 0 °C 3.2: brine 4.1: thionyl chloride / tetrahydrofuran / 1 h / 20 °C 5.1: ammonium hydroxide / tetrahydrofuran / 1 h / 20 °C 6.1: pyridine; oxalyl dichloride / N,N-dimethyl-formamide / 0.5 h / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: pyridinium hydrobromide perbromide; triethylamine / dichloromethane / 2 h / 0 °C 2.1: sodium hydride / tetrahydrofuran; mineral oil / 1 h / 0 °C 2.2: 3 h / 0 °C 3.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / Inert atmosphere 3.2: 1 h / -78 °C / Inert atmosphere 3.3: -78 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: pyridinium hydrobromide perbromide; triethylamine / dichloromethane / 2 h / 0 °C 2.1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / water; N,N-dimethyl-formamide / 2 h / 130 °C / Inert atmosphere 3.1: sodium hydride / tetrahydrofuran; mineral oil / 1 h / 0 °C 3.2: 3 h / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: pyridinium hydrobromide perbromide; triethylamine / dichloromethane / 2 h / 0 °C 2.1: sodium hydride / tetrahydrofuran; mineral oil / 1 h / 0 °C 2.2: 3 h / 0 °C 3.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / Inert atmosphere 3.2: 1 h / -78 °C / Inert atmosphere 3.3: -78 - 20 °C 4.1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / water; N,N-dimethyl-formamide / 2 h / 130 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1.1: pyridinium hydrobromide perbromide; triethylamine / dichloromethane / 2 h / 0 °C 2.1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / water; N,N-dimethyl-formamide / 2 h / 130 °C / Inert atmosphere 3.1: boron tribromide / dichloromethane / 1 h / 0 °C 3.2: brine 4.1: thionyl chloride / tetrahydrofuran / 1 h / 20 °C 5.1: ammonium hydroxide / tetrahydrofuran / 1 h / 20 °C 6.1: pyridine; oxalyl dichloride / N,N-dimethyl-formamide / 0.5 h / 0 °C 7.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.25 h / 20 °C 7.2: 1.5 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1.1: pyridinium hydrobromide perbromide; triethylamine / dichloromethane / 2 h / 0 °C 2.1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / water; N,N-dimethyl-formamide / 2 h / 130 °C / Inert atmosphere 3.1: boron tribromide / dichloromethane / 1 h / 0 °C 3.2: brine 4.1: thionyl chloride / tetrahydrofuran / 1 h / 20 °C 5.1: ammonium hydroxide / tetrahydrofuran / 1 h / 20 °C 6.1: pyridine; oxalyl dichloride / N,N-dimethyl-formamide / 0.5 h / 0 °C 7.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.25 h / 20 °C 7.2: 1.5 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1.1: pyridinium hydrobromide perbromide; triethylamine / dichloromethane / 2 h / 0 °C 2.1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / water; N,N-dimethyl-formamide / 2 h / 130 °C / Inert atmosphere 3.1: boron tribromide / dichloromethane / 1 h / 0 °C 3.2: brine 4.1: thionyl chloride / tetrahydrofuran / 1 h / 20 °C 5.1: ammonium hydroxide / tetrahydrofuran / 1 h / 20 °C 6.1: pyridine; oxalyl dichloride / N,N-dimethyl-formamide / 0.5 h / 0 °C 7.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.25 h / 20 °C 7.2: 1.5 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1.1: pyridinium hydrobromide perbromide; triethylamine / dichloromethane / 2 h / 0 °C 2.1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / water; N,N-dimethyl-formamide / 2 h / 130 °C / Inert atmosphere 3.1: boron tribromide / dichloromethane / 1 h / 0 °C 3.2: brine 4.1: thionyl chloride / tetrahydrofuran / 1 h / 20 °C 5.1: ammonium hydroxide / tetrahydrofuran / 1 h / 20 °C 6.1: pyridine; oxalyl dichloride / N,N-dimethyl-formamide / 0.5 h / 0 °C 7.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.25 h / 20 °C 7.2: 1.5 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1.1: pyridinium hydrobromide perbromide; triethylamine / dichloromethane / 2 h / 0 °C 2.1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / water; N,N-dimethyl-formamide / 2 h / 130 °C / Inert atmosphere 3.1: boron tribromide / dichloromethane / 1 h / 0 °C 3.2: brine 4.1: thionyl chloride / tetrahydrofuran / 1 h / 20 °C 5.1: ammonium hydroxide / tetrahydrofuran / 1 h / 20 °C 6.1: pyridine; oxalyl dichloride / N,N-dimethyl-formamide / 0.5 h / 0 °C 7.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.25 h / 20 °C 7.2: 1.5 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 8 steps 1.1: pyridinium hydrobromide perbromide; triethylamine / dichloromethane / 2 h / 0 °C 2.1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / water; N,N-dimethyl-formamide / 2 h / 130 °C / Inert atmosphere 3.1: boron tribromide / dichloromethane / 1 h / 0 °C 3.2: brine 4.1: thionyl chloride / tetrahydrofuran / 1 h / 20 °C 5.1: ammonium hydroxide / tetrahydrofuran / 1 h / 20 °C 6.1: pyridine; oxalyl dichloride / N,N-dimethyl-formamide / 0.5 h / 0 °C 7.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.25 h / 20 °C 7.2: 1.5 h / 20 °C 8.1: sodium tetrahydroborate; calcium chloride / tetrahydrofuran; ethanol / 14 h / 20 °C 8.2: 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 8 steps 1.1: pyridinium hydrobromide perbromide; triethylamine / dichloromethane / 2 h / 0 °C 2.1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / water; N,N-dimethyl-formamide / 2 h / 130 °C / Inert atmosphere 3.1: boron tribromide / dichloromethane / 1 h / 0 °C 3.2: brine 4.1: thionyl chloride / tetrahydrofuran / 1 h / 20 °C 5.1: ammonium hydroxide / tetrahydrofuran / 1 h / 20 °C 6.1: pyridine; oxalyl dichloride / N,N-dimethyl-formamide / 0.5 h / 0 °C 7.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.25 h / 20 °C 7.2: 1.5 h / 20 °C 8.1: sodium tetrahydroborate; calcium chloride / tetrahydrofuran; ethanol / 14 h / 20 °C 8.2: 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: pyridinium hydrobromide perbromide; triethylamine / dichloromethane / 2 h / 0 °C 2.1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / water; N,N-dimethyl-formamide / 2 h / 130 °C / Inert atmosphere 3.1: boron tribromide / dichloromethane / 1 h / 0 °C 3.2: brine 4.1: thionyl chloride / tetrahydrofuran / 1 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | With sodium hydride In N,N-dimethyl-formamide at 5℃; for 1.75h; Inert atmosphere; | 9.C C: 2,5-Dimethyl-l-[4-(4-methyl-pyrazol-l-ylmethyl)-benzyl]-lH-pyrrole-3-carboxylic acid methyl ester A solution of methyl 2,5-dimethyl-lH-pyrrole-3-carboxylate (0.382 g, 2.492 mmol) in anhydrous DM F (8 mL) was cooled in an ice-bath, then treated sequentially portionwise with sodium hydride (0.071 g, 2.95 mmol), then l-(4-(chloromethyl)benzyl)-4-methyl-lH-pyrazole (0.50 g, 2.266 mmol) and the mixture allowed to stir at ~ 5 °C for 1 hour. The ice-bath was removed and the mixture stirred for a further 45 min. Further sodium hydride (~0.5 eq) was added and the mixture allowed to stir overnight. The reaction was quenched with water (40 mL) and attempted to extract into DCM(3 x 40 mL), but presence of DMF caused emulsion. Combined DCM layers were washed with brine, dried (IN^SO,^), filtered and concentrated. Brine (40 mL) was added to the initial aqueous layer and this extracted with EtOAc (3 x 40 mL). The combined EtOAc layers were washed with water (3 x 20 mL), brine (30 mL), dried (MgSO,^), and concentrated with the DCM extract residue (4 mbar 55 QC) to remove residual DM F. The compound was purified by chromatography (silica) eluting with a gradient of 0 to 70% EtOAc/lso-Hexanes to afford 2,5-dimethyl-l-[4-(4-methyl-pyrazol-l-ylmethyl)-benzyl]-lH-pyrrole-3-carboxylic acid methyl ester (602 mg, 1.748 mmol, 77 % yield) as a pale yellow oil which crystallized slowly on standing. [M+H]+ = 338 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: methyl 2,5-dimethyl-1H-pyrrole-3-carboxylate With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; Stage #2: 1-Chloro-4-(chloromethyl)benzene In N,N-dimethyl-formamide; mineral oil at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0 - 20 °C 1.2: 20 °C 2.1: sodium hydroxide / water; tetrahydrofuran / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0 - 20 °C 1.2: 20 °C 2.1: sodium hydroxide / water; tetrahydrofuran / 20 °C 3.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 2 h / 140 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
40% | With diphenyl hydrogen phosphate; methanesulfonic acid; hydrogen; tris(acetylacetonato)ruthenium(III) In tetrahydrofuran at 160℃; for 24h; Autoclave; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With chlorosulfonic acid In acetonitrile at 0 - 20℃; for 3h; | 2.1 (1) Synthesis of 4-(chlorosulfonyl)-2,5-dimethyl-1H-pyrrole-3-carboxylic acid methyl ester Weigh 2,5-dimethyl-1H-pyrrole-3-carboxylic acid methyl ester (1.5g, 11.96mmol) and dissolve it in 20mL acetonitrile, stir and cool to 0 with an ice-water bath, and slowly add chlorosulfonic acid (1.5g, 11.96mmol) 13.94g, 119.6mmol). After the addition is complete, react at 0-20°C for 3 hours. When the reaction is complete, add the reaction liquid dropwise to crushed ice, then extract with ethyl acetate, and dry the organic phase over anhydrous sodium sulfate , The crude product 4-(chlorosulfonyl)-2,5-dimethyl-1H-pyrrole-3-carboxylic acid methyl ester was obtained by distillation under reduced pressure, which was directly used in the next step. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: chlorosulfonic acid / acetonitrile / 3 h / 0 - 20 °C 2: N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: chlorosulfonic acid / acetonitrile / 3 h / 0 - 20 °C 2: N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / 20 °C 3: acetonitrile / 1 h / 80 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: sodium (meta)periodate / water monomer / 0.17 h / 20 °C 2.1: tetrabutylammonium bromide; potassium carbonate / acetonitrile / 17 h / 65 °C 3.1: sodium tetrahydridoborate / 0.33 h / 0 °C 4.1: N-[3-(N,N-dimethylamino)-propyl]-N'-ethyl-carbodiimide hydrochloride / dichloromethane / 1 h / 20 °C 4.2: 24 h / 20 °C 5.1: 300 °C / Pyrolysis; Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: Sodium hydrogenocarbonate / water monomer / 24 h 2.1: sodium (meta)periodate / water monomer / 0.17 h / 20 °C 3.1: tetrabutylammonium bromide; potassium carbonate / acetonitrile / 17 h / 65 °C 4.1: sodium tetrahydridoborate / 0.33 h / 0 °C 5.1: N-[3-(N,N-dimethylamino)-propyl]-N'-ethyl-carbodiimide hydrochloride / dichloromethane / 1 h / 20 °C 5.2: 24 h / 20 °C 6.1: 300 °C / Pyrolysis; Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: tetrabutylammonium bromide; potassium carbonate / acetonitrile / 17 h / 65 °C 2.1: sodium tetrahydridoborate / 0.33 h / 0 °C 3.1: N-[3-(N,N-dimethylamino)-propyl]-N'-ethyl-carbodiimide hydrochloride / dichloromethane / 1 h / 20 °C 3.2: 24 h / 20 °C 4.1: 300 °C / Pyrolysis; Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: sodium tetrahydridoborate / 0.33 h / 0 °C 2.1: N-[3-(N,N-dimethylamino)-propyl]-N'-ethyl-carbodiimide hydrochloride / dichloromethane / 1 h / 20 °C 2.2: 24 h / 20 °C 3.1: 300 °C / Pyrolysis; Inert atmosphere |
Tags: 69687-80-5 synthesis path| 69687-80-5 SDS| 69687-80-5 COA| 69687-80-5 purity| 69687-80-5 application| 69687-80-5 NMR| 69687-80-5 COA| 69687-80-5 structure
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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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