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CAS No. : | 16135-36-7 | MDL No. : | MFCD00955996 |
Formula : | C7H8N2O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | OCARFFAPQGYGBP-UHFFFAOYSA-N |
M.W : | 152.15 | Pubchem ID : | 592353 |
Synonyms : |
|
Num. heavy atoms : | 11 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.14 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 39.92 |
TPSA : | 65.21 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) : | -6.82 cm/s |
Log Po/w (iLOGP) : | 1.39 |
Log Po/w (XLOGP3) : | 0.58 |
Log Po/w (WLOGP) : | 0.46 |
Log Po/w (MLOGP) : | -0.26 |
Log Po/w (SILICOS-IT) : | 0.47 |
Consensus Log Po/w : | 0.53 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.42 |
Solubility : | 5.78 mg/ml ; 0.038 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.52 |
Solubility : | 4.57 mg/ml ; 0.03 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -1.73 |
Solubility : | 2.87 mg/ml ; 0.0188 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.36 |
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 |
---|---|---|
55% | With lithium hydroxide monohydrate; water In ethanol at 20 - 80℃; for 2 h; | To a stirred solution of methyl 4-aminopyridine-3-carboxylate (2 g, 13.15 mmol) in EtOHwater(120 mL, 1:1), LiOH·H20 (1.21 g, 28.80 mmol) was added at RT and heated at 80 °Cfor 2 h (TLC indicated complete consumption of starting material). The volatiles wereremoved under reduced pressure to give the crude compound which was dissolved in water(30 mL), washed with EtOAc (2 x 25 mL) to remove the non-polar impurities. The aqueouslayer was acidified with 1 N HCl till pH= 1, and extracted with EtOAc (2 x 10 mL). Thecombined organic extracts were concentrated under reduced pressure to give the cruderesidue which was crystallized from MeOH (20 mL) to obtain 4-aminopyridine-3-carboxylicacid (1 g, 55percent) as an off-white solid.LCMS (ESI+): m/z: 139.31 [M+Ht. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99.1% | With trifluoroacetic acid In dichloromethane at 20℃; for 2 h; | [4-TERT-BUTOXYCARBONYLAMINO-NICOTINIC] acid methyl ester (9.08 g, 36.0 [MMOL)] was dissolved in 50/50 TFA/DCM (100 mL) solution and stirred for 2 hours at room temperature. Concentration of the mixture under reduced pressure was followed by [RE-DISSOLUTION] in DCM (100 mL), washing with saturated sodium bicarbonate, drying over sodium sulfate, and concentration under reduced pressure. The corresponding de- protected product of Formula 505,4-amino-nicotinic acid methyl ester (5.43 g, 99.1percent) was obtained was obtained in sufficient purity to be carried forward for use in the next step. MS [(CI)] M/E: 153.1. |
92% | for 0.75 h; | Methyl4- (Boc-amino) pyridine-3-carboxylate (2.38 g, 9.4 mmol) was dissolved in TFA (20 mL) and the solution was allowed to stir for 45 min. The solvent was removed in vacuo and the residue was partitioned between 25percent isopropanol in chloroform and satd aq sodium bicarbonate. The layers were separated and the aqueous phase was extracted again with 25percent isopropanol in chloroform. The combined organic extracts were dried(MgSO4), filtered and concentrated in vacuo to give a solid which was washed with diisopropyl ether and dried in vacuo to give the title compound (1. 327 g, 92percent) as an off-white solid. 1NMR' IS-MS, m/e 153.1 (mol) Analysis for C7H8N2 2 : Calcd : C, 55.26 ; H, 5.30 ; N, 18.41 ; Found: C, 55.31 ; H, 5.36 ; N, 18. 42. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
51% | With ammonium acetate In methanol at 80℃; for 2 h; Microwave irradiation | In a CEM microwave vial, 3-methyl-5-nitro-pyrimidin-4-one (300 mg, 1.94 mmol), methylacetoacetate (2.7 g, 23.27 mmol), ammonium acetate (1.79 g, 23.22 mmol) and MeOH (8.0mL) were added and irradiated at 80 °C for 2 h (TLC indicated complete consumption ofstarting material). The reaction mixture was concentrated under reduced pressure to give thecrude product which was purified by column chromatography (100-200 silica gel, 40 g, 5-10percent MeOH-DCM) to afford methyl 4-aminopyridine-3-carboxylate; this reaction mixturewas carried out in 6 batches (300 mg each), the crude material after work-up was combinedand purified to afford methyl 4-aminopyridine-3-carboxylate (900 mg, 51percent) as a yellowsolid.LCMS (ESI+): m/z: 153.43 [M+Ht. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67% | Reflux; Cooling | Step a): Methyl 4-aminopyridine-3-carboxylate A little at a time, 4400 mg (31.86 mmol) of 4-aminopyridine-3-carboxylic acid are added to 12 ml of ice-cooled concentrated sulfuric acid. 70 ml of methanol are then added slowly. The reaction mixture is stirred under reflux (oil bath temperature 75° C.) for 20 h. The reaction solution is poured onto about 120 g of ice and neutralized with sodium carbonate. After extraction with dichloromethane, the organic phase is dried over magnesium sulfate and filtered. After 24 h of standing, the title compound crystallizes from the filtrate. Yield: 3310 mg (67percent of theory) LC-MS (Method 9): Rt=1.59 min; MS (ESIpos): m/z=153 [M+H]+. |
10.3 g | at 0 - 85℃; | To a solution of 4-aminopyridine-3-carboxylic acid (17 g, 0.123 mol) in MeOH (300 mL) was added H2SO4 (45 mL) dropwise at 0 °C. The reaction mixture was heated to reflux at 85 °C overnight. The progress of reaction was monitored by TLC. After completion of the reaction, the mixture was concentrated under reduced pressure to remove MeOH, residue was basified with a saturated aqueous solution of Na2C03 (400 mL), extracted with EtOAc (3x500 mL). The combined organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford methyl 4-aminopyridine-3-carboxylate (10.3 g) as a white solid. |
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