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CAS No. : | 1681-37-4 | MDL No. : | MFCD00160304 |
Formula : | C5H5N3O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | IUPPEELMBOPLDJ-UHFFFAOYSA-N |
M.W : | 139.11 | Pubchem ID : | 548803 |
Synonyms : |
|
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 : | 1.0 |
Molar Refractivity : | 37.46 |
TPSA : | 84.73 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.76 cm/s |
Log Po/w (iLOGP) : | 0.81 |
Log Po/w (XLOGP3) : | 0.55 |
Log Po/w (WLOGP) : | 0.58 |
Log Po/w (MLOGP) : | -0.53 |
Log Po/w (SILICOS-IT) : | -1.44 |
Consensus Log Po/w : | -0.01 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.43 |
Solubility : | 5.2 mg/ml ; 0.0374 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.9 |
Solubility : | 1.75 mg/ml ; 0.0126 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -1.02 |
Solubility : | 13.3 mg/ml ; 0.0957 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 2.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.97 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-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 |
---|---|---|
97% | With palladium 10% on activated carbon; hydrogen In tetrahydrofuran at 10℃; for 24 h; | The commercially available 3-nitropyridin-4-amine (50 g, 395 mmol) in the mixture of methanol (500 ml) and THF (500 ml) was hydrogenated with 10 percent Pd/C (5 g) as a catalyst at 10°C (1 atm) for 24 h. After uptake of (3 eq), the catalyst was filtered off and the filtrate was evaporated. 38 g of the title intermediate 8 was obtained, (Yield 97 percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | at 100℃; Sealed tube | A mixture of 3-nitropyridin-4-amine (LXVIII) (10 g, 71.88 mmol) and acetic acid (100 ml) was added to a sealed tube followed by addition of NaOAc (29.50 g, 359 mmol) and dropwise addition of bromine (4.43 ml 86.3 mmol) under stirring. The sealed tube was heated at 100° C. for overnight. The reaction mixture was concentrated under vacuum to obtain a solid which was dissolved in water, basified with saturated aqueous NaHCO3 and extracted with DCM. The combined organic extracts were dried and concentrated to produce 3-bromo-5-nitropyridin-4-amine (LXIX) as a yellow solid (13.7 g, 62.8 mmol, 87percent yield). 1H NMR (DMSO-d6, 500 MHz) δ ppm 8.58 (s, 1H), 9.19 (s, 1H); ESIMS found for C5H4BrN3O2 m/z 218.1 (M+H). |
77% | Stage #1: at 100℃; for 28 h; in sealed tube Stage #2: With sodium hydrogencarbonate In water |
Step 1[00202] A mixture of 3-nitropyridin-4-amine (XLV) (10 g, 71.94mmol) and acetic acid (120 ml) was added to a sealed tube followed by addition of NaOAc (29.50g, 93.52mmol) and dropwise addition of bromine (4.7ml 359.7 mmol) under stirring. The sealed tube was heated at 100°C for 28 h until TLC showed consumption of starting material. The reaction mixture was concentrated to obtain a solid which was dissolved in water, basified with NaHC03 and extracted with EtOAc. The combined organic extracts were dried and concentrated to produce 3-bromo-5-nitropyridin-4-amine (XLVI) as a yellow solid (12 g, 55 mmol, 77percent yield). 1H NMR (DMSO-d6) δ ppm 9.19 ( s, 1H), 8.58 (s, 1H); ESIMS found for C5H4BrN302m/z 217, 219 (M+, M+2). |
77% | at 100℃; for 28 h; | A mixture of 3-nitropyridin-4-amine (LVII) (10 g, 71.94 mmol) and acetic acid (120 mL) was added to a sealed tube followed by addition of NaOAc (29.50 g, 93.52 mmol) and dropwise addition of bromine (4.7 ml 359.7 mmol) under stirring. The sealed tube was heated at 100° C. for 28 h until TLC showed consumption of starting material. The reaction mixture was concentrated to obtain a solid which was dissolved in water, basified with NaHCO3 and extracted with EtOAc. The combined organic extracts were dried and concentrated to produce 3-bromo-5-nitropyridin-4-amine (LVIII) as a yellow solid (12 g, 55 mmol, 77percent yield). 1H NMR (DMSO-d6) δ ppm 9.19 (s, 1H), 8.58 (s, 1H); ESIMS found for C5H4BrN3O2 m/z 217, 219 (M+, M+2). |
77% | With bromine; sodium acetate; acetic acid In water at 100℃; for 28 h; Sealed tube | Step a;A mixture of 3-nitropyridin-4-amine (XII) (10 g, 71.94 mmol) and acetic acid (120 ml) was added to a sealed tube followed by addition of NaOAc (29.50g, 93.52mmol) and dropwise addition of bromine (4.7ml 359.7 mmol) under stirring. The sealed tube was heated at 100°C for 28 h until TLC showed consumption of starting material.The reaction mixture was concentrated to obtain a solid which was dissolved in water, basified with NaHCO3 and extracted with ethyl acetate. The combined organic extracts were dried and concentrated to produce 3-bromo-5-nitropyridin-4-amine (XIII) as a yellow solid (12 g, 55 mmol, 77percent yield). 1H NMR (DMSO-d6) δ ppm 9.19 (s, 1H), 8.58 (s, 1H); ESIMS found for C5H4BrN3O2 m/z 217, 219 (M+, M+2). |
77% | With bromine; sodium acetate In acetic acid at 100℃; for 28 h; | Step 1 (0852) A mixture of 3-nitropyridin-4-amine (LXVI) (10 g, 71.94 mmol) and acetic acid (120 mL) was added to a sealed tube followed by addition of NaOAc (29.50 g, 93.52 mmol) and dropwise addition of bromine (4.7 ml 359.7 mmol) under stirring. The sealed tube was heated at 100° C. for 28 h until TLC showed consumption of starting material. The reaction mixture was concentrated to obtain a solid which was dissolved in water, basified with NaHCO3 and extracted with EtOAc. The combined organic extracts were dried and concentrated to produce 3-bromo-5-nitropyridin-4-amine (LXVII) as a yellow solid (12 g, 55 mmol, 77percent yield). 1H NMR (DMSO-d6) δ ppm 9.19 (s, 1H), 8.58 (s, 1H); ESIMS found for C5H4BrN3O2 m/z 217, 219 (M+, M+2). |
76.5% | at 100℃; for 28 h; Sealed tube | [0667] A mixture of 3-nitropyridin-4-amine (LXVIII) (10 g, 71.94 mmol) and acetic acid (120 mL) was added to a sealed tube followed by addition of NaOAc (29.50g, 93.52mmol) and dropwise addition of bromine (4.7 mL, 359.7 mmol) under stirring. The sealed tube was heated at 100°C for 28 h until TLC showed consumption of starting material. The reaction mixture was concentrated to obtain a solid which was dissolved in water, basified with NaHCC and extracted with EtOAc. The combined organic extracts were dried and concentrated to produce 3-bromo-5- nitropyridin-4-amine (LXIX) as a yellow solid (12 g, 55 mmol, 76.5percent yield). NMR (DMSO- d6) δ ppm 9.19 ( s, 1H), 8.58 (s, 1H); ESIMS found for CjiLBrNsOz mlz 217, 219 (M+, M+2). |
67% | at 20℃; for 48 h; | To a stirred mixture of 38 (3.0 g, 21.6 mmol) and NaOAc (2.7 g, 32.4 mmol) in glacial AcOH (72 mL) was added dropwise a mixture of Br2 (3.8 g, 23.8 mmol) in glacial AcOH (24 mL), then the mixture was stirred for 48 h at room temperature. The reaction was quenched with saturated aqueous Na2S2O3 (10 mL), then the solvent was removed under reduced pressure. The resulting yellow solid was collected by filtration and washed with water (50 mL), then dried under vacuum. The crude product was recrystallized from n-hexane/EtOAc (3:1) to give 39 (3.2 g, 67percent yield) as yellow crystals. 1H and 13C NMR data were in agreement with those previously reported.28 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | at 20 - 90℃; for 8 h; | Under ice bath, pyridin-4-amine (5.0 g, 50.0 mmol) was solubilizedin concentrated sulfuric acid (20 mL), then fuming nitric acid(2.5 mL) was added drop-wise at 0–10 C. After stirring for 5 h at rt,90 C for 3 h and continue to stir at rt overnight. Then the mixturewas poured into ice-water, adjust the pH value to 7 with ammonia,The resulting precipitate was filtered, dried under reduced pressureto yield the title compound as a yellow solid (5.1 g, 70percent).MS [M+H]+ m/z: 140.04. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86.6% | With ammonium acetate; triethylamine In water; ethyl acetate | EXAMPLE 1 Preparation of 3-Nitro-4-aminopyridine A 500 ml 3-neck round bottom flask equipped with a condenser, thermometer and mechanical stirrer was charged with 78.4 g (0.383 mol) of 4-ethoxy-3-nitropyridine hydrochloride, 118.1 g (1.53 mol) of ammonium acetate and 183 ml of water. The stirred reaction mixture was refluxed for 71/2 hours and the progress of the reaction was followed by thin layer chromatography employing a 10:1 ethyl acetate:triethylamine solvent system. The reaction flask was chilled to approximately 4° C. after the pH of the mixture was adjusted from 5.2 to 8.1 with 60 ml of concentrated ammonium hydroxide. The yellow precipitate was collected by filtration, washed twice with chilled water and dried under vacuum at 50° C. for 10 hours. A total dry weight of 46.15 g (86.6percent yield) of 3-nitro-4-aminopyridine was obtained. The product was verified by NMR and compared to an authentic sample. Analysis calculated for C5 H5 N3 O2: Theory: C, 43.17; H, 3.62; N, 30.21; Found: C, 42.93; H, 3.81; N, 29.97. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With ammonium acetate; triethylamine In phosphorus pentaoxide; ethyl acetate | EXAMPLE 2 Preparation of 3-Nitro-4-aminopyridine A 25 ml round bottom flask was fitted with a reflux condenser and magnetic stirrer and placed in an oil bath. The flask was charged with 1.0 g (5.95 mmol) of 4-ethoxy-3-nitropyridine and 5.0 g (65 mmol) of ammonium acetate. The reaction mixture was heated at 120° C. to provide a homogeneous liquid. The progress of the reaction was followed by thin layer chromotography employing a 10:1 ethyl acetate:triethylamine solvent system. After 21/2 hours the reaction mixture was cooled and poured into water. The yellow precipitate was collected by filtration, washed with water and dried in vacuo at 60° C. over phosphorus pentoxide. A total of 620 mg of 3-nitro-4-aminopyridine was obtained and chromatographically verified by comparison to an authentic reference standard. Yield 75percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79.3%. | With ammonium acetate In hydrogenchloride | EXAMPLE 3 Preparation of 3-Nitro-4-aminopyridine A 22 liter 4-neck flask fitted with a reflux condenser, thermometer and mechanical stirrer was charged with 1300 g (6.35 mol) of 4-ethoxy-3-nitropyridine hydrochloride, 2438 g (31.62 mol) of ammonium acetate and 13 1. of glacial acetic acid. The reaction mixture was refluxed for 3 hours and cooled. The volatiles were evaporated under reduced pressure and the residue was dissolved in 1N hydrochloric acid. The insoluble material was removed by filtration and the pH of the filtrate was adjusted to approximately 8.5 with concentrated ammonium hydroxide. The precipitated solid was collected by filtration, washed with water and dried in a forced air oven to provide 701 g of 3-nitro-4-aminopyridine. Yield 79.3percent. mp=187°-195° C. The identity of the product was also confirmed by chromatography in a 10:1 ethyl acetate:triethylamine solvent system by comparison to a reference standard. |
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