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CAS No. : | 4664-01-1 |
Formula : | C7H4N2O2 |
M.W : | 148.12 |
SMILES Code : | O=C1NC(C2=C1C=CN=C2)=O |
MDL No. : | MFCD00013439 |
InChI Key : | SJSABZBUTDSWMJ-UHFFFAOYSA-N |
Pubchem ID : | 72926 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 11 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.0 |
Num. rotatable bonds | 0 |
Num. H-bond acceptors | 3.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 39.61 |
TPSA ? Topological Polar Surface Area: Calculated from |
59.06 ?2 |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
0.59 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
-0.35 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
-0.42 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
0.06 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
1.05 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
0.19 |
Log S (ESOL):? ESOL: Topological method implemented from |
-0.94 |
Solubility | 16.9 mg/ml ; 0.114 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (Ali)? Ali: Topological method implemented from |
-0.43 |
Solubility | 55.3 mg/ml ; 0.373 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-2.38 |
Solubility | 0.61 mg/ml ; 0.00412 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 |
No |
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 |
-7.45 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 |
1.0 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) |
1.37 |
* 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% | With bromine; sodium hydroxide; In water; at 90℃; for 0.666667h;Cooling with ice; | Step 1 To 10percent aqueous sodium hydroxide solution (100 mL) was added bromine (1.93 mL, 38.6 mmol) under ice-cooling, and 1H-pyrrolo[3,4-c]pyridine-1,3(2H)-dione (5.20 g, 35.1 mmol) was subsequently added. 10percent-Aqueous sodium hydroxide solution (60 mL) was added to the reaction mixture, and the mixture was stirred with heating at 90° C. for 40 min. After allowing to cool to room temperature, 50percent sulfuric acid was added to adjust the reaction mixture to pH 3. The precipitated insoluble material was collected by filtration, and the solid was washed with water to give 3-aminoisonicotinic acid as a pale-yellow powder (5.00 g, 100percent). 1H-NMR (200 MHz, DMSO-d6) delta: 7.46 (1H, d, J=5.1 Hz), 7.73 (1H, d, J=5.1 Hz), 8.21 (1H, s). |
68.33% | NaOH (10percent aqueous, 640 ml) was cooled to 7° C. and bromine (15 ml, 286.82 mmol) added dropwise. Pyrrolo[3,4-c]pyridine-1,3-dione (41.711 g, 281.6 mmol) was then added to the reaction mixture before it was heated to 80° C. for 30 minutes. After this time the reaction was allowed to warm to 37° C. and the pH modified to 5.5 by the addition of acetic acid (70 ml). A suspension formed that was removed by filtration and washed with 20 ml of ice cold methanol to give the title compound (26.58 g, 68.33percent) in a suitably clean form to be used without any further purification. m/z (LC-MS, ESP): 139 [M+H]+, R/T=0.72 mins. | |
67% | Bromine (3. 5 ml, 69.0 mmol) was added to a solution of 10 percent aqueous sodium hydroxide (120 ml) at 0 C to give a pale yellow solution. To this solution was added 3,4-pyridinedicarboximide (10 g, 67. 5 mmol) and the reaction was heated at 80 C for 45 min. The reaction was cooled in a water bath and acidified by the addition of acetic acid (12. 5 ml) causing precipitation. The solid was collected, rinsed with water(50 ml), thenMeOH(50 ml) and dried to give the title compound as a beige solid (6.28 g, 67 percent).1H NMR (360 MHz, DMSO)5 8. 06 (1H, s), 7.60(1H, d,J5. 1), 7.34(1H, d,J5. 1), 3.19 (2H, brs). M/z (ES+) 139 (M+H+). |
64% | Following the procedures of Zhou et al (2001) Bioorg. Med. Chem. Lett.9(8):2061-2071, bromine (1.22 ml, 23.9 mmol) was slowly added to a cooled (50C) 2.5N solution of NaOH (60 ml, 150 mmol) and after stirring for 5 minutes pyrrolo[3,4-c]pyridine- 1,3-dione (3.5 g, 23.6 mmol) was added. The temperature was raised to 8O0C and the mixture was stirred for 1 hour before being cooled to ambient temperature. Acetic acid (5.9 ml, 98.3 mmol) was cautiously added (N.B.: gas evolution) and the solution stirred for 10 minutes whereby a precipitate formed that was collected by filtration. The solid was washed with water (20 ml) and MeOH (20 ml) then dried to afford the title compound as a yellow solid (2.1 g, 64percent). | |
62% | With sodium hydroxide; bromine; In water; at 0 - 80℃; for 0.75h; | A solution of10percent aqueousNaOH (416 mL) was cooled to0 C and treated with bromine (28.2 g 176 mmol) portionwise via pipette while keeping the temperature below 5 C. To this mixture was added 3,4-pyridinedicarboximide (25.78 g, 174mmol), and the cooling bath was removed. The reaction was heated to80 C for 45 min, then allowed to cool in an ice bath. When the temperature fell to 60 C, the dropwise addition of HOAc (50 mL) was started. Cooling was continued until the temperature reached 15 C. A yellow precipitate formed. The solid was filtered, rinsed with water, then dried under vacuum to give 14.9 g of product (108 mmol,62percent). 1NMR IS-MS, m/e 139(m+1) |
57% | With bromine; In sodium hydroxide; | Preparation 18 3-Aminopyridine-4-carboxylic acid To an ice cold mixture of 3,4-pyridinedicarboximide (5.2 g, 35.11 mmol) in 10percent sodium hydroxide (85 mL) was added bromine (1.84 mL, 35.8 mmol), dropwise. The resulting solution was heated to 80° C. for 1 hour, cooled on ice, and the acidity was carefully adjusted to pH 5.5 with acetic acid. The precipitate was collected, washed well with water and air dried to afford 3-aminopyridine-4-carboxylic acid (2.74 g, 57percent). NMR (DMSO d6) delta8.20 (s, 1H), 7.72 (d, J=5 Hz, 1H), 7.45 (d, J=5 Hz, 1H). The material was used without purification. |
57% | Step A: 3-Aminoisonicotinic acid: 2H-Pyrrolo[3,4-c]pyridine-1,3-dione (204.16 g, 1378.4 mmol) was dissolved in 10percent NaOH (3.3 L) and the solution was cooled to an internal temperature of 7° C. (ice/salt bath). Bromine (73.424 mL, 1433.5 mmol) was added dropwise while maintaining the internal temperature below 10° C. After completion of the addition, the reaction was heated to an internal temperature of 80-85° C. for 90 minutes. The reaction mixture was cooled to 20-30° C. in an ice bath then acetic acid (323.21 mL, 5651.2 mmol) was added dropwise. The reaction was stirred and cooled to 5° C. The solids were collected by vacuum filtration, washed with cold water then air-dried to provide the product (108.86 g, 57percent). | |
57% | With bromine; In sodium hydroxide; | Preparation 18 3-Aminopyridine-4-carboxylic acid To an ice cold mixture of 3,4-pyridinedicarboximide (5.2 g, 35.11 mmol) in 10percent sodium hydroxide (85 mL) was added bromine (1.84 mL, 35.8 mmol), dropwise. The resulting solution was heated to 80° C. for 1 hour, cooled on ice, and the acidity was carefully adjusted to pH 5.5 with acetic acid. The precipitate was collected, washed well with water and air dried to afford 3-aminopyridine-4-carboxylic acid (2.74 g, 57percent). 1H NMR (DMSO d6) delta8.20 (s,1 H), 7.72 (d, J=5 Hz, 1 H), 7.45 (d, J=5 Hz, 1 H). The material was used without purification. |
Preparation 5 Step 1: 3,4 Pyridine-dicarboximide (10.0 g, 67.5 [MMOL)] was dissolved in 10percent aqueous [NAOH] (162 g) and the solution was cooled to an internal temperature [OF 7 OC] in an ice-salt bath. Bromine (3.6 ml ; 70 [MMOL)] was added dropwise. After the addition, the solution was heated for 45 min at a bath temperature of 80-85 [°C.] The yellow solution was then cooled to an internal temperature of 37 [°C,] and [GLACIAL ACOH] (17 ml) were added dropwise to a pH of 5.5. The resulting mixture was refrigerated overnight. The solid formed was filtered and washed with water (5 ml) and CH30H (5 [ML).] The reaction yielded 6.35 g. of product, m. p. 280-285 [°C] (decomp. ). | ||
With sodium hydroxide; bromine; In water; at 0 - 85℃; for 0.75h; | 3,4 Pyridine-dicarboximide 288 (10.0 g; 67.5 mmoles) was dissolved in 162 g. of 10percent aqueous NaOH and the solution was cooled to an internal temperature of 70C in an ice-salt bath. Bromine (3.6 ml; 70 mmoles) was added dropwise. After the addition, the solution was heated for 45 minutes at a bath temperature of 80-85 0C. The yellow solution was then cooled to an internal temperature of 37 0C, then 17 ml of glacial acetic acid were added dropwise to a pH of 5.5. The resulting mixture was saved overnight in a refrigerator. The solid formed was filtered and washed with 5 ml of water and 5 ml of methanol. The reaction yielded 6.35 g. of product 289 melting at 280-285 0C (decomp.). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With bromine; In tetrahydrofuran; methanol; sodium hydroxide; water; acetic acid; | EXAMPLE 29 3,4 Pyridine-dicarboximide 288 (10.0 g; 67.5 mmoles) was dissolved in 162 g. of 10% aqueous NaOH and the solution was cooled to an internal temperature of 7 C. in an ice-salt bath. Bromine (3.6 ml; 70 mmoles) was added dropwise. After the addition, the solution was heated for 45 minutes at a bath temperature of 80-85 C. The yellow solution was then cooled to an internal temperature of 37 C., then 17 ml of glacial acetic acid were added dropwise to a pH of 5.5. The resulting mixture was saved overnight in a refrigerator. The solid formed was filtered and washed with 5 ml of water and 5 ml of methanol. The reaction yielded 6.35 g. of product 289 melting at 280-285 C. (decomp.). Solid Compound 289 (9.5 gr.; 69 mmoles) was carefully added in three aliquots to a slurry of lithium aluminum hydride (9.5 gr.; 250 mmoles) in 200 ml of dry tetrahydrofuran. The resulting hot mixture was stirred at room temperature for two days. After cooling in an ice bath, the reaction was quenched with very careful sequential dropwise addition of 10 ml of water, followed by 10 ml of 15% aqueous NaOH, then by 30 ml of water. The resulting solid was filtered through a pad of Celite and washed several times with THF. The oil obtained after evaporation of the solvent, solidified on standing. The reaction mixture was purified by flash chromatography on silica gel using 5%MeOH(NH3)/EtOAc as eluent yielding 6.21 (72%) of Compound 290. LC-MS: m/z=125 (M+1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
57% | With bromine; In sodium hydroxide; | Preparation 18 3-Aminopyridine-4-carboxvlic acid To an ice cold mixture of 3,4-pyridinedicarboximide (5.2 g, 35.11 mmol) in 10percent sodium hydroxide (85 mL) was added bromine (1.84 mL, 35.8 mmol), dropwise. The resulting solution was heated to 80°C for 1 hour, cooled on ice, and the acidity was carefully adjusted to pH 5.5 with acetic acid. The precipitate was collected, washed well with water and air dried to afford 3-aminopyridine4-carboxylic acid (2.74 g, 57percent). NMR (DMSO d6) delta 8.20 (s, 1 H), 7.72 (d, J = 5 Hz, 1 H), 7.45 (d, J = 5 Hz, 1 H). The material was used without purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62% | Step lTo a solution of compound [137] (3 g, 20.2 mmol, leq) in glacial acetic acid (30 ml), Zn dust (5.26 g, 81.0 mmol, 4 eq.) was added and the reaction mixture was refluxed at 100 C for 4 h. The reaction mixture was cooled to room temperature and the solvent was evaporated. The reaction mass was made basic with aqueous NaHC03 to pH 8 and extracted with chloroform. The aqueous layer was concentrated and further extracted with chloroform. The combined organic layer was dried over Na2S04 and evaporated to give [138] as a peach white solid (1.7 g, 62%).ESIMS: 135 (M+ + 1) |
Tags: 4664-01-1 synthesis path| 4664-01-1 SDS| 4664-01-1 COA| 4664-01-1 purity| 4664-01-1 application| 4664-01-1 NMR| 4664-01-1 COA| 4664-01-1 structure
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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 |
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