Structure of 5470-18-8
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Jang, Mingyeong ; Lim, Taeho ; Park, Byoung Yong ; Han, Min Su ;
Abstract: In this study, we developed a metal-free and highly chemoselective method for the reduction of aromatic nitro compounds. This reduction was performed using tetrahydroxydiboron [B2(OH)4] as the reductant and 4,4'-bipyridine as the organocatalyst and could be completed within 5 min at room temperature. Under optimal conditions, nitroarenes with sensitive functional groups, such as vinyl, ethynyl, carbonyl, and halogen, were converted into the corresponding anilines with excellent selectivity while avoiding the undesirable reduction of the sensitive functional groups.
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Purchased from AmBeed: 607-35-2 ; 578-66-5 ; 613-50-3 ; 100-19-6 ; 579-71-5 ; 3034-94-4 ; 5683-43-2 ; 99-92-3 ; 13534-97-9 ; 5676-60-8 ; 5470-18-8 ; 619-45-4 ; 553-26-4 ; 580-15-4 ; 611-34-7 ; 619-72-7 ; 100-13-0 ; 540-37-4 ; 1849-25-8 ; 4487-59-6 ; 555-16-8 ; 6298-19-7 ; 556-08-1 ; 953-26-4 ; 54060-30-9 ; 62-23-7 ; 607-34-1 ; 3867-18-3 ; 873-74-5 ; 3544-24-9 ; 94-52-0 ; 1520-21-4 ; 5470-34-8 ; 619-50-1 ; 586-39-0 ; 934-22-5 ; 402-54-0 ; 15411-43-5 ; 455-14-1 ; 17763-80-3 ; 3085-54-9 ; 1942-30-9 ; 1694-20-8 ; 6305-66-4 ; 41656-75-1 ; 6393-17-5 ; 4309-66-4
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CAS No. : | 5470-18-8 |
Formula : | C5H3ClN2O2 |
M.W : | 158.54 |
SMILES Code : | O=[N+](C1=CC=CN=C1Cl)[O-] |
MDL No. : | MFCD00006232 |
InChI Key : | UUOLETYDNTVQDY-UHFFFAOYSA-N |
Pubchem ID : | 79613 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P301+P312-P302+P352-P304+P340-P305+P351+P338 |
Num. heavy atoms | 10 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.0 |
Num. rotatable bonds | 1 |
Num. H-bond acceptors | 3.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 38.07 |
TPSA ? Topological Polar Surface Area: Calculated from |
58.71 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.01 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
1.64 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
1.64 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
0.68 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
-0.09 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
0.98 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.23 |
Solubility | 0.925 mg/ml ; 0.00583 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-2.49 |
Solubility | 0.518 mg/ml ; 0.00327 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-2.01 |
Solubility | 1.55 mg/ml ; 0.00979 mol/l |
Class? Solubility class: Log S scale |
Soluble |
GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg |
High |
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg |
Yes |
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) |
No |
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) |
No |
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) |
No |
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) |
No |
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) |
No |
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) |
No |
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from |
-6.1 cm/s |
Lipinski? Lipinski (Pfizer) filter: implemented from |
0.0 |
Ghose? Ghose filter: implemented from |
None |
Veber? Veber (GSK) filter: implemented from |
0.0 |
Egan? Egan (Pharmacia) filter: implemented from |
0.0 |
Muegge? Muegge (Bayer) filter: implemented from |
1.0 |
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat |
0.55 |
PAINS? Pan Assay Interference Structures: implemented from |
0.0 alert |
Brenk? Structural Alert: implemented from |
3.0 alert: heavy_metal |
Leadlikeness? Leadlikeness: implemented from |
No; 1 violation:MW<1.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
1.85 |
* 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 |
---|---|---|
100% | at 80℃; for 8 h; Sealed tube | To a solution of 3-nitro-2-chloropyridine (4.0 g, 25.2 mmol) in 15 mL 2-methoxyethanol was added methylamine (2.0 M in THF, 32 mL). The reactionwas stirred for 8 hr at 80 °C in a sealed tube. After cooling to rt, the reaction mixture was evaporated to afford 15 quantitatively (3.6 g, 23.2 mmol). 1H NMR (500 MHz, CDCl3) δ 8.47 – 8.37 (m, 2H), 8.20 (s, 1H), 6.64 (dd, J = 8.3, 4.4 Hz, 1H), 3.17 (d, J = 4.8 Hz, 3H). 13C NMR (126 MHz, CDCl3) δ 156.0, 153.5, 135.4, 111.7, 28.4. HRMS (ESI+) m/z calcd for C6H8N3O2+ 154.0617, found 154.0610. |
98.5% | at 0 - 20℃; for 3 h; | Methylamine (33percent in EtOH) (1 10 mL, 883 mmol) was placed in a 500 mL three necked round bottom flask. It was cooled to 0 °C using ice bath. 2-chloro-3-nitropyridine (20 g, 126 mmol) was added to the above solution in portions as this is an exothermic reaction. After the addition was complete the reaction mixture was stirred for 2 h at 0 °C and later 1 h at room temperature. Solvent was concentrated and residue was taken in 500 mL of water and extracted with EtOAc 3 x 150 mL. Combine organic layer was dried over Na2SC"4, filtered and concentrated to give a bright orangish yellow solid(19 g , 98.5percent). |
95.76% | With triethylamine In dichloromethane at 20℃; for 5 h; | 24 mL of methylamine, 39.5 mL of triethylamine was added to 240 mL of dichloromethane, and 30 g(0.18 mol) of 2-chloro-3-nitropyridine, and the reaction was completed at room temperature for 5 h. After completion of the reaction, the reaction solution was washed three times with waterInto anhydrous sodium sulfate in addition to water, suction filtration, steaming, yellow crystalline solid product 44.8g (yield 95.76percent). |
86% | With sodium acetate In water; acetonitrile at 20℃; Heating / reflux | 2-chloro-3-nitropyridine 70.0 g, 0.44 mol) was dissolved in recently distilled acetonitrile (400 mL) under stirring. Sodium acetate (55.2 g, 0.67 mol) and 30percent aqueous solution of methylamine (111 mL) were added under vigorous stirring. The obtained suspension was stirred at room temperature for 30 min, refluxed for 1 h, and kept overnight at room temperature. The yellow reaction mixture was concentrated under reduced pressure to remove approximately 300 mL of the solvent. The residue was diluted with 20percent aqueous solution of K2CO3 (1 L) under stirring. The yellow precipitate was filtered off, washed with water (3° * 200 mL), and dried to afford W-Methyl-3-nitropyridin-2-amine in 86percent (58.14 g, 0.38 mol) yield as bright yellow crystals. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98.5% | With methylamine In ethanol; water | Synthesis of N-methyl-3-nitropyridin-2-amine Methylamine (33percent in EtOH) (110 mL, 883 mmol) was placed in a 500 mL three necked round bottom flask. It was cooled to 0° C. using ice bath. 2-chloro-3-nitropyridine (20 g, 126 mmol) was added to the above solution in portions as this is an exothermic reaction. After the addition was complete the reaction mixture was stirred for 2 h at 0° C. and later 1 h at room temperature. Solvent was concentrated and residue was taken in 500 mL of water and extracted with EtOAc 3*150 mL. Combine organic layer was dried over Na2SO4, filtered and concentrated to give a bright orangish yellow solid (19 g, 98.5percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | In methanol; at 0℃; for 4h; | A suspension of sodium methoxide (40.5 g, 0.750 mol) in 200 mL of methanol was slowly added to a solution of 2-chloro-3- nitro-pyridine (79.3 g, 0.500 mol) in 800 mL of methanol at 0 °C. The reaction mixture was stirred for 4 hours and then poured into 1000 g of ice. The resulting precipitate was filtered, washed with water, and dried to give 2-methoxy-3-nitro-pyridine (70. g, 0.45 mmol, 90 percent) as a white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium hydroxide; thiourea; In ethanol; water; | Example 98A 3-nitropyridine-2-thiol 2-mercapto-3-nitropyridine was prepared by treating 3-nitro-2-chloro-pyridine (50 g, 0.0317 mol) with thiourea (24 g, 0.0317 mol) in 200 mL of ethanol at reflux for several hours. After the reaction mixture was allowed to cool, 7.19 mL solution of KOH (42.8 g in 115 mL of water) was added and the resulting mixture was heated at reflux for 3 hours. The crude reaction mixture was cooled to room temperature and then concentrated to 50% of its volume in vacuo. | |
2-mercapto-3-nitropyridine was prepared by treating 3-nitro-2-chloro-pyridine (50 g, 0.0317 mol) with thiourea (24 g, 0.0317 mol) in 200 ML of ethanol at reflux for several hours.After the reaction mixture was allowed to cool, 7.19 ML solution of KOH (42.8 g in 115 ML of water) was added and the resulting mixture was heated at reflux for 3 hours.The crude reaction mixture was cooled to room temperature and then concentrated to 50% of its volume in vacuo.After diluting with 300 ML of water, the product was isolated by vacuum filtration as an orange solid that was used without further purification. MS (DCI/NH3) m/z 157 (M+H)+. 1H NMR (300 MHz, DMSO-d6) delta 5.76 (m, 1H), 7.67 (dd, J=8.46, 4.78 Hz, 1H), 8.63 (dd, J=8.46, 1.47 Hz, 1H), 8.73 (dd, J=4.60, 1.65 Hz, 1H). | ||
3-nitropyridine-2-thiol 2-mercapto-3-nitropyridine was prepared by treating 3-nitro-2-chloro-pyridine (50 g, 0.0317 mol) with thiourea (24 g, 0.0317 mol) in 200 ML of ethanol at reflux for several hours.After the reaction mixture was allowed to cool, 7.19 ML solution of KOH (42.8 g in 115 ML of water) was added and the resulting mixture was heated at reflux for 3 hours.The crude reaction mixture was cooled to room temperature and then concentrated to 50% of its volume in vacuo.After diluting with 300 ML of water, the product was isolated by vacuum filtration as an orange solid that was used without further purification. MS (DCI/NH3) m/z 157 (M+H)+. 1H NMR (300 MHz, DMSO-d6) delta 5.76 (m, 1H), 7.67 (dd, J=8.46, 4.78 Hz, 1H), 8.63 (dd, J=8.46, 1.47 Hz, 1H), 8.73 (dd, J=4.60, 1.65 Hz, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With triethylamine; In 1,4-dioxane; for 1h;Reflux; | At room temperature, dissolve 2-chloro-3-nitropyridine (300mg, 1.89mmol) in 10mL 1,4-dioxane, add TEA (0.78mL, 5.67mmol) and morpholine (181mg, 2.08mmol) , Reflux for 1 hour,LC-MS monitoring showed that the reaction was complete. The reaction solution was concentrated to remove the solvent, and 30 mL of water and 50 mL of ethyl acetate were added to dissolve the residue. The ethyl acetate layer was separated. The aqueous layer was extracted with ethyl acetate (50 mL×2). The organic layers were combined and dried over anhydrous sodium sulfate. Rotate to dryness to obtain 4-(3-nitropyridin-2-yl)morpholine 4A as a yellow solid (376 mg, 95%), which was directly used in the next reaction without further purification. |
82.2% | With potassium carbonate; In N,N-dimethyl-formamide; at 85℃; for 6h; | 2-Chloro-3-nitropyridine (20.0 g, 126.2 mmol) was dissolved in DMF (160 mL)Add potassium carbonate (52.3 g, 378.5 mmol),Slowly added morpholine (22.0 g, 252.3 mmol),The reaction was carried out at 85 C for 6 h. The reaction is completed,Cool to room temperature,Add 200mL of pure water,Extracted with ethyl acetate (200 mL × 2),Collect organic phase,Dry over anhydrous sodium sulfate,Filter out the solids,Evaporate the solvent under reduced pressure.The residue was passed through a silica gel column (mobile phase: PE: EA = 10:1).4-(3-Nitropyridin-2-yl)morpholine yellow solid 21.7 g,yield: 82.2%. |
With triethylamine; In tetrahydrofuran; at 65℃; for 2h;Inert atmosphere; | General procedure: In a 100 mL three neck round bottom flask equipped with a stirring bar and reflux condenser, 2-chloro-3-nitropyridine 5, 1 equiv. of primary or secondary amine, and Et 3 N (1 equiv.) were dissolved in THF (3 mL). The reaction mixture is refluxed at 65 C for 2 h. After the reaction was complete (analyzed by TLC), the mixture was allowed to reach room temperature. The mixture was washed with water (30 mL), and extracted with ethyl acetate (3 X 30 mL). The combined organic phases were washed with brine and dried over anhydrous Na 2 SO 4 , filtered, and concentrated under reduced pressure. The crude oil was purified via column chromatography with silica gel to obtain the appropriate 2-amino-3-nitropyridine derivative 8a or 8b. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium hydroxide; In dimethyl sulfoxide; | 15.1 Synthesis of 2-(5-amino-2-chloro-4-fluorophenoxy)-3-nitropyridine (Intermediate IIa) (Process 1). A mixture of <strong>[84478-72-8]5-amino-2-chloro-4-fluorophenol</strong> (0.64 g), powdered potassium hydroxide (0.24 g), and 2-chloro-3-nitropyridine (0.76 g) in dimethylsulfoxide (15 ml) was heated at 110 C. with stirring for 2 hours. The solution was processed and the resulting oil chromatographed on silica gel eluding with methanol:methylene chloride, 3:97, to yield 2-(5-amino-2-chloro-4-fluorophenoxy)-3-nitropyridine (Intermediate IIa) as a yellow semi-solid (0.45 g). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium carbonate; methylamine; In toluene; | PREPARATION 104 2-Methylamino-3-nitropyridine A procedure similar to that described in Preparation 66 was repeated, except that 24.9 g of 2-chloro-3-nitropyridine, 41.7 g of sodium carbonate, 22.7 ml of a 30 % ethanolic solution of methylamine were reacted in 250 ml of toluene. After working up the product as described in Preparation 66, the resulting crude product was crystallized by trituration with isopropanol, to give 24.0 g of the title compound, melting at 52-53 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With sodium methylate; In methanol; | EXAMPLE 12 Synthesis of 2-methoxy-3-nitropyridine STR27 2-Chloro-3-nitropyridine (25 g, 0.157 mol) was suspended in methanol (300 ml) and sodium methoxide (17 g, 0.315 mol) was added. The mixture was refluxed for 2 hr and part of the solvent removed under reduced pressure. The reaction mixture was diluted with water (1 litre) and the precipitate collected by filtration. The white solid obtained was washed with more water and dried under vacuum to give the title compound (18.2 g, 75percent). 1 H NMR (CDCl3): 8.42 (dd, J=5, 2 Hz, 1H); 8.28 (dd, J=8, 2 Hz, 1H); 7.06 (dd, J=8, 5 Hz, 1H); 4.13 (s, 3H) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine; In ethanol; | EXAMPLE 8 2-(4-Chlorophenyl)-3-(1H-imidazol-2-ylmethyl)-3H-imidazo[4,5-b]pyridine A suspension of 2-chloro-3-nitropyridine (7.74 g, 0.0490 mol) and 2-aminomethyl imidazole dihydrochloride (10.0 g, 0.0588 mol) in absolute ethanol (250 mL) was stirred at room temperature and triethylamine (11.88 g, 0.118 mol) was added. The mixture was heated at reflux for 4 hours, additional triethylamine (5.9 g, 0.0588 mol) was added, and refluxing was continued for 2 additional hours. The solvents were removed under reduced pressure, and the residue was partitioned between ethyl acetate and water. The insoluble solid was collected by filtration and was combined with the product that was obtained by separating the layers of the filtrate followed by washing the ethyl acetate with saturated sodium chloride solution. The product was recrystallized from ethyl acetate/isopropyl ether/light petroleum ether to give 3.10 g of crude N-(1H-imidazol-2-ylmethyl)-3-nitro-2-pyridine. An additional recrystallization of 0.5 g of the solid from ethyl acetate/light petroleum ether gave 0.33 g, mp 144-146 C. Anal. for C9 H9 N5 O2: Calcd: C, 49.31; H, 4.14; N, 31.95. Found: C, 49.36; H, 4.05; N, 31.88. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92.5% | With potassium carbonate; In N,N-dimethyl-formamide; | (2) A mixture of 2-chloro-3-nitropyridine (4.76 g, 30 mmols), <strong>[129150-68-1]N-tert-butoxycarbonyl-3-hydroxyphenethylamine</strong> (7.11 g, 30 mmols), potassium carbonate (4.14 g, 30 mmols) and N,N-dimethylformamide (50 ml) was stirred at 100C for 12 hours. The reaction mixture was cooled, then poured into water, and then extracted with ethyl acetate. The extract was washed with water, and then dried with anhydrous magnesium sulfate, and the solvent was evaporated away. The residue was purified through silica gel column chromatography to give an yellow oil of tert-butyl [2-[3-(3-nitro-2-pyridyloxy)phenyl]ethyl]carbamate (10.1 g, 92.5 %). Elemental Analysis for C18H21N3O5: Calcd.: C, 60.16; H, 5.89; N, 11.69 Found: C, 60.11; H, 5.98; N, 11.58 1H-NMR (CDCl3) delta: 1.43(9H,s), 2.83(2H,t,J=6.6Hz), |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
46% | With N-ethyl-N,N-diisopropylamine; In ethanol; at 85℃; for 18h; | Example 1Ethyl N-(tert-butoxycarbonyl)-4-[(3-nitropyridin-2-yl)amino]-L-phenylalaninate (Intermediate 1)To a stirred solution of <strong>[67630-01-7]N-(tert-butyloxycarbonyl)-4-amino-L-phenylalanine ethyl ester</strong> (2Og) (CAS No. 67630-01-7) and DIPEA (13ml) in EtOH (200ml) is added 2-Chloro- 3-nitropyridine (11.85g) (CAS No. 34515-82-7). The reaction is heated at 85C for 18 hours. The reaction is allowed to cool and the majority of the EtOH removed in vacuo. The residue is partitioned between EtOAc (100ml) and water (50ml). The aqueous layer is extracted with EtOAc (50ml) and the combined organic layers are washed with brine (20ml), dried (MgSO4) and concentrated in vacuo. The residue is purified in two batches by chromatography on silica, eluting with EtOAc-heptane to afford the title compound as an orange solid (13.17g, 46%). LCMS (Method A) 429 [M-H]-, RT 4.17 mins. 1 H NMR 300 MHz (CDCI3) 51.25 (t, 3H), 1.40 (s, 9H), 3.1 (m, 2H), 4.2 (q, 2H), 4.6 (dd, 1 H), 5.00 (d,1 H), 6.8 (dd, 1 H), 7.15 (d, 2H), 7.6 (d, 2H), 8.45-8.55 (m, 2H). |
46% | With N-ethyl-N,N-diisopropylamine; In ethanol; at 85℃; for 18h; | Example 1Ethyl N-(tert-butoxycarbonyl)-4-[(3-nitropyridin-2-yl)amino]-L-phenylalaninate(Intermediate 1)To a stirred solution of <strong>[67630-01-7]N-(tert-butyloxycarbonyl)-4-amino-L-phenylalanine ethyl ester</strong> (2Og) (CAS No. 67630-01-7) and DIPEA (13mL) in EtOH (20OmL) is added 2-Chloro- 3-nitropyridine (11.85g) (CAS No. 34515-82-7). The reaction is heated at 85C for 18 hours. The reaction is allowed to cool and the majority of the EtOH removed in vacuo. The residue is partitioned between EtOAc (10OmL) and water (5OmL). The aqueous phase is extracted with EtOAc (5OmL) and the combined organic extracts washed with brine (2OmL), dried (MgSO4) and concentrated in vacuo. The residue is purified in two batches by chromatography on silica, eluting with EtOAc-heptane to afford the title compound as an orange solid (13.17g, 46%). LCMS (Method A) 429 [M-H]-, RT 4.17 mins. 1H NMR 300 MHz (CDCI3) .51.25 (t, 3H), 1.40 (s, 9H), 3.1 (m, 2H), 4.2 (q, 2H), 4.6 (dd, 1 H), 5.00 (d, 1 H), 6.8 (dd, 1 H), 7.15 (d, 2H), 7.6 (d, 2H), 8.45-8.55 (m, 2H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63.5% | With potassium carbonate; In dimethyl sulfoxide; at 110℃; for 2h; | Tert-butyl(trans-3-aminocyclobutyl)carbamate (1.38 g, 7.41 mmol), 2-chloro-3-nitropyridine (1.25 g, 7.88 mmol) and potassium carbonate (0.655 ml, 10.85 mmol) were combined in dry dimethylsulfoxide (20 mL) and heated at 110 C. After 2 hours the reaction was cooled and partitioned between ethyl acetate (300 mL) and water (300 mL). The organic was dried with magnesium sulfate and evaporated to dryness under reduced pressure. Purification using silica chromatography (dichloromethane to ethyl acetate gradient) gave the desired tert-butyl(trans-3-((3-nitropyridin-2-yl)amino)cyclobutyl)carbamate (1.45 g, 4.70 mmol, 63.5% yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
0.12 g | With caesium carbonate; In N,N-dimethyl-formamide; at 60℃; for 16h; | To a stirred solution of 2-chloro-3-nitropyridine (CAS Number 5470-18-8; 0.5 g, 3.154 mmol) in DMF (10 ml) was added l-(tert-butyl) 3-methyl 3-hydroxypyrrolidine-l,3-dicarboxylate (Intermediate C; 0.62 g, 2.524 mmol) and Cs2C03(3.08 g, 9.463 mmol) at rt. The reaction mixture was stirred at 60C for 16 h. The resulting reaction mixture was poured into ice cold water (100 ml) and extracted with EtOAc (2 x 70 ml). The combined organic phase was dried over Na2S04, filtered and concentrated under reduced pressure. The resulting residue was purified by flash chromatography using neutral alumina (25% EtOAc in hexane) yielding l-(tert-butyl) 3-methyl 3-((3-nitropyridin-2- yl)oxy)pyrrolidine-l,3-dicarboxylate (0.12 g, 0.327 mmol). LCMS: Method 1, 2.20 min, MS: ES+ 368.5; 1H NMR (400 MHz, DMSO-d6) delta ppm: 8.51 (d, J=8.0 Hz, 1 H), 8.44 (dd, J=1.6 Hz, 4.8 Hz, 1 H), 7.30 -7.34 (m, 1 H), 3.97 - 4.04 (m, 1 H), 3.68 - 3.71 (m, 1 H), 3.63 (s, 3 H), 3.44 - 3.48 (m, 2 H), 2.41 - 2.45 (m, 2 H), 1.38 (s, 9 H). |
Tags: 5470-18-8 synthesis path| 5470-18-8 SDS| 5470-18-8 COA| 5470-18-8 purity| 5470-18-8 application| 5470-18-8 NMR| 5470-18-8 COA| 5470-18-8 structure
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Precautionary Statements-General | |
Code | Phrase |
P101 | If medical advice is needed,have product container or label at hand. |
P102 | Keep out of reach of children. |
P103 | Read label before use |
Prevention | |
Code | Phrase |
P201 | Obtain special instructions before use. |
P202 | Do not handle until all safety precautions have been read and understood. |
P210 | Keep away from heat/sparks/open flames/hot surfaces. - No smoking. |
P211 | Do not spray on an open flame or other ignition source. |
P220 | Keep/Store away from clothing/combustible materials. |
P221 | Take any precaution to avoid mixing with combustibles |
P222 | Do not allow contact with air. |
P223 | Keep away from any possible contact with water, because of violent reaction and possible flash fire. |
P230 | Keep wetted |
P231 | Handle under inert gas. |
P232 | Protect from moisture. |
P233 | Keep container tightly closed. |
P234 | Keep only in original container. |
P235 | Keep cool |
P240 | Ground/bond container and receiving equipment. |
P241 | Use explosion-proof electrical/ventilating/lighting/equipment. |
P242 | Use only non-sparking tools. |
P243 | Take precautionary measures against static discharge. |
P244 | Keep reduction valves free from grease and oil. |
P250 | Do not subject to grinding/shock/friction. |
P251 | Pressurized container: Do not pierce or burn, even after use. |
P260 | Do not breathe dust/fume/gas/mist/vapours/spray. |
P261 | Avoid breathing dust/fume/gas/mist/vapours/spray. |
P262 | Do not get in eyes, on skin, or on clothing. |
P263 | Avoid contact during pregnancy/while nursing. |
P264 | Wash hands thoroughly after handling. |
P265 | Wash skin thouroughly after handling. |
P270 | Do not eat, drink or smoke when using this product. |
P271 | Use only outdoors or in a well-ventilated area. |
P272 | Contaminated work clothing should not be allowed out of the workplace. |
P273 | Avoid release to the environment. |
P280 | Wear protective gloves/protective clothing/eye protection/face protection. |
P281 | Use personal protective equipment as required. |
P282 | Wear cold insulating gloves/face shield/eye protection. |
P283 | Wear fire/flame resistant/retardant clothing. |
P284 | Wear respiratory protection. |
P285 | In case of inadequate ventilation wear respiratory protection. |
P231 + P232 | Handle under inert gas. Protect from moisture. |
P235 + P410 | Keep cool. Protect from sunlight. |
Response | |
Code | Phrase |
P301 | IF SWALLOWED: |
P304 | IF INHALED: |
P305 | IF IN EYES: |
P306 | IF ON CLOTHING: |
P307 | IF exposed: |
P308 | IF exposed or concerned: |
P309 | IF exposed or if you feel unwell: |
P310 | Immediately call a POISON CENTER or doctor/physician. |
P311 | Call a POISON CENTER or doctor/physician. |
P312 | Call a POISON CENTER or doctor/physician if you feel unwell. |
P313 | Get medical advice/attention. |
P314 | Get medical advice/attention if you feel unwell. |
P315 | Get immediate medical advice/attention. |
P320 | |
P302 + P352 | IF ON SKIN: wash with plenty of soap and water. |
P321 | |
P322 | |
P330 | Rinse mouth. |
P331 | Do NOT induce vomiting. |
P332 | IF SKIN irritation occurs: |
P333 | If skin irritation or rash occurs: |
P334 | Immerse in cool water/wrap n wet bandages. |
P335 | Brush off loose particles from skin. |
P336 | Thaw frosted parts with lukewarm water. Do not rub affected area. |
P337 | If eye irritation persists: |
P338 | Remove contact lenses, if present and easy to do. Continue rinsing. |
P340 | Remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P341 | If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P342 | If experiencing respiratory symptoms: |
P350 | Gently wash with plenty of soap and water. |
P351 | Rinse cautiously with water for several minutes. |
P352 | Wash with plenty of soap and water. |
P353 | Rinse skin with water/shower. |
P360 | Rinse immediately contaminated clothing and skin with plenty of water before removing clothes. |
P361 | Remove/Take off immediately all contaminated clothing. |
P362 | Take off contaminated clothing and wash before reuse. |
P363 | Wash contaminated clothing before reuse. |
P370 | In case of fire: |
P371 | In case of major fire and large quantities: |
P372 | Explosion risk in case of fire. |
P373 | DO NOT fight fire when fire reaches explosives. |
P374 | Fight fire with normal precautions from a reasonable distance. |
P376 | Stop leak if safe to do so. Oxidising gases (section 2.4) 1 |
P377 | Leaking gas fire: Do not extinguish, unless leak can be stopped safely. |
P378 | |
P380 | Evacuate area. |
P381 | Eliminate all ignition sources if safe to do so. |
P390 | Absorb spillage to prevent material damage. |
P391 | Collect spillage. Hazardous to the aquatic environment |
P301 + P310 | IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. |
P301 + P312 | IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell. |
P301 + P330 + P331 | IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. |
P302 + P334 | IF ON SKIN: Immerse in cool water/wrap in wet bandages. |
P302 + P350 | IF ON SKIN: Gently wash with plenty of soap and water. |
P303 + P361 + P353 | IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower. |
P304 + P312 | IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell. |
P304 + P340 | IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing. |
P304 + P341 | IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P305 + P351 + P338 | IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. |
P306 + P360 | IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes. |
P307 + P311 | IF exposed: call a POISON CENTER or doctor/physician. |
P308 + P313 | IF exposed or concerned: Get medical advice/attention. |
P309 + P311 | IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician. |
P332 + P313 | IF SKIN irritation occurs: Get medical advice/attention. |
P333 + P313 | IF SKIN irritation or rash occurs: Get medical advice/attention. |
P335 + P334 | Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages. |
P337 + P313 | IF eye irritation persists: Get medical advice/attention. |
P342 + P311 | IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician. |
P370 + P376 | In case of fire: Stop leak if safe to Do so. |
P370 + P378 | In case of fire: |
P370 + P380 | In case of fire: Evacuate area. |
P370 + P380 + P375 | In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion. |
P371 + P380 + P375 | In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion. |
Storage | |
Code | Phrase |
P401 | |
P402 | Store in a dry place. |
P403 | Store in a well-ventilated place. |
P404 | Store in a closed container. |
P405 | Store locked up. |
P406 | Store in corrosive resistant/ container with a resistant inner liner. |
P407 | Maintain air gap between stacks/pallets. |
P410 | Protect from sunlight. |
P411 | |
P412 | Do not expose to temperatures exceeding 50 oC/ 122 oF. |
P413 | |
P420 | Store away from other materials. |
P422 | |
P402 + P404 | Store in a dry place. Store in a closed container. |
P403 + P233 | Store in a well-ventilated place. Keep container tightly closed. |
P403 + P235 | Store in a well-ventilated place. Keep cool. |
P410 + P403 | Protect from sunlight. Store in a well-ventilated place. |
P410 + P412 | Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF. |
P411 + P235 | Keep cool. |
Disposal | |
Code | Phrase |
P501 | Dispose of contents/container to ... |
P502 | Refer to manufacturer/supplier for information on recovery/recycling |
Physical hazards | |
Code | Phrase |
H200 | Unstable explosive |
H201 | Explosive; mass explosion hazard |
H202 | Explosive; severe projection hazard |
H203 | Explosive; fire, blast or projection hazard |
H204 | Fire or projection hazard |
H205 | May mass explode in fire |
H220 | Extremely flammable gas |
H221 | Flammable gas |
H222 | Extremely flammable aerosol |
H223 | Flammable aerosol |
H224 | Extremely flammable liquid and vapour |
H225 | Highly flammable liquid and vapour |
H226 | Flammable liquid and vapour |
H227 | Combustible liquid |
H228 | Flammable solid |
H229 | Pressurized container: may burst if heated |
H230 | May react explosively even in the absence of air |
H231 | May react explosively even in the absence of air at elevated pressure and/or temperature |
H240 | Heating may cause an explosion |
H241 | Heating may cause a fire or explosion |
H242 | Heating may cause a fire |
H250 | Catches fire spontaneously if exposed to air |
H251 | Self-heating; may catch fire |
H252 | Self-heating in large quantities; may catch fire |
H260 | In contact with water releases flammable gases which may ignite spontaneously |
H261 | In contact with water releases flammable gas |
H270 | May cause or intensify fire; oxidizer |
H271 | May cause fire or explosion; strong oxidizer |
H272 | May intensify fire; oxidizer |
H280 | Contains gas under pressure; may explode if heated |
H281 | Contains refrigerated gas; may cause cryogenic burns or injury |
H290 | May be corrosive to metals |
Health hazards | |
Code | Phrase |
H300 | Fatal if swallowed |
H301 | Toxic if swallowed |
H302 | Harmful if swallowed |
H303 | May be harmful if swallowed |
H304 | May be fatal if swallowed and enters airways |
H305 | May be harmful if swallowed and enters airways |
H310 | Fatal in contact with skin |
H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
H313 | May be harmful in contact with skin |
H314 | Causes severe skin burns and eye damage |
H315 | Causes skin irritation |
H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
Sorry,this product has been discontinued.
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