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CAS No. : | 58483-95-7 | MDL No. : | MFCD06659499 |
Formula : | C6H5ClN2O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | WCZUTMZMEAPPIX-UHFFFAOYSA-N |
M.W : | 172.57 | Pubchem ID : | 22736791 |
Synonyms : |
|
Num. heavy atoms : | 11 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 40.61 |
TPSA : | 76.21 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) : | -6.49 cm/s |
Log Po/w (iLOGP) : | 0.89 |
Log Po/w (XLOGP3) : | 1.21 |
Log Po/w (WLOGP) : | 1.02 |
Log Po/w (MLOGP) : | -1.1 |
Log Po/w (SILICOS-IT) : | 0.68 |
Consensus Log Po/w : | 0.54 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.56 |
Log S (ESOL) : | -2.01 |
Solubility : | 1.69 mg/ml ; 0.00978 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.41 |
Solubility : | 0.676 mg/ml ; 0.00392 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -1.65 |
Solubility : | 3.85 mg/ml ; 0.0223 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.65 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H332-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 |
---|---|---|
88% | With sodium acetate In 2-methoxy-ethanol at 120℃; for 6 h; | A mixture of compound 5-amino-2-chloropyridine-4-carboxylic acid(1000 g, 5.8 mol) was dissolved in 5000 mlEthylene glycol monomethyl ether, AddedFormamidine hydrochloride(1867 g, 23.2 mol), sodium acetate (2360 g, 17.4 mol). The reaction was heated to 120 ° C for 6 hours. After the reaction was complete, the reaction was cooled to room temperature, poured into 4000 ml of water and extracted twice with ethyl acetate. The organic phase was combined, dried and concentrated to afford the crude product which was filtered to give 6-chloropyridine And [3,4-d] pyrimidin-4 (3H) ketone (924 g, 5-1 mol) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81.5% | at 120℃; for 4 h; | Step 1: containing 1.3 g of 5-amino-2-chloro nicotinic acid (7.6 mmol) and 0.66 g methyl acyl imide amide (formimidamide) (15.1 mmol, 2.0 equiv.) Of acetic acid was heated to 120 acid to give 6-chloro-pyrrolo for 4 hours, the solvent is removed after the addition of an aqueous solution containing sodium hydrogen carbonate solution is adjusted to a value of 8, filtered, and then [3,4-d] pyrimidin -4 (3H) - one (1.1 g, yield 81.5percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83.9% | at 140℃; | Step (e): 6-CHLORO-3H-PYRIDO [3, 4-D] PYRIMIDIN-4-ONE A suspension of 5-amino-2-chloro-isonicotinic acid in formamide (240 mL) was heated at an internal temperature of 140°C overnight with stirring. The mixture was cooled to room temperature, diluted with water (600mL), and stirred for 1 hour. The resulting solid was collected by filtration, washed with water, and dried to give 17. 20g of 6-chloro-3H-pyrido [3, 4-d] PYRIMIDIN-4-ONE as a brown solid (83. 9percent yield). 1H NMR (400 MHz, DMSO-D6) d ppm 7.9 (s, 1H), 8.2 (s, 1H), 8.9 (s, 1H), 12.7 (bs, 1H) MS (APCI) M+1 = 182.0 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | for 18 h; Heating / reflux | Step (e) 6-Chloro-3H-pyrido [3,4-d] pyrimidin-4-one A 1 L round bottomed flask was charged with 5-amino-2-chloro- isonicotinic acid (69.5 g, 0.40 moles), formamidine acetate (84 g, 0.81 moles, 2 mole equivalents), and 600 mL of methoxyethanol. The resulting solution was heated at reflux for 18 hours. After cooling to 5°C, a precipitate was collected by filtration, washed twice with methoxyethanol, and dried overnight in the vacuum oven at 45°C. The reaction yielded 67 g (92percent total yield) of 6-chloro-3H- pyrido [3, 4-D] PYRIMIDIN-4-ONE as a tan solid that was sufficiently pure by NMR to use in the next reaction. 8H (DMSO) 12.70 (1 H, s), 8.86 (1 H, d), 8. 19 (1 H, s), 7.93 (1 H, d) MS [M+H3+ 182 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With trifluoroacetic acid In dichloromethane | 5-Amino-2-chloropyridine-4-carboxylic acid. A stirred suspension of 5-[N-(tert-butoxycarbonyl)amino]-2-chloropyridine-4-carboxylic acid (1.91 g, 7 mmol) in CH2 Cl2 (200 mL) is treated slowly with trifluoroacetic acid until homogeneous (ca. 12 mL). The solution is stirred overnight and extracted with dilute NH4 OH, and the aqueous layer is then acidified with dilute HCl to gave a precipitate of 5-amino-2-chloropyridine-4-carboxylic acid (1.05 g, 87percent yield). 1 H NMR (DMSO) δ 9.01 (2H, m), 8.03 (1H, s), 7.48 (1H, s). |
80% | With trifluoroacetic acid In dichloromethane at 20℃; | Step (d): 5-AMINO-2-CHLORO-ISONICOTINIC acid A suspension of 5-tert-butoxycarbonylamino-2-chloro-isonicotinic acid in methylene chloride (600mL) was treated dropwise at room temperature with TFA until the solid had dissolved into solution (95 mL). The reaction mixture was stirred overnight under nitrogen at room temperature, evaporated to dryness, diluted with water, and the solid collected by filtration. The solid was washed with water, dried under low heat and house vacuum, to afford 19.55g of 5-amino- 2-chloro-isonicotinic acid as a yellow solid (93.6percent yield). 1H NMR (400 MHz, DMSO-D6) 8 ppm 7.5 (s, 2H), 8.0 (s, 2H) MS (APCI) M+1= 173.0; Step (d): 5-AMINO-2-CHLORO-ISONICOTINIC acid A 3 L round bottomed flask was charged with 5-tert- BUTOXYCARBONYLAMINO-2-CHLORO-ISONICOTINIC acid (138 g, 0.51 moles), 1 L of CH2C12, and 400 mL of TFA. The resulting orange solution was stirred overnight at room temperature. One liter of H20 was added to the reaction solution, which caused a solid to precipitate out. The solid was collected, washed once with H2O and dried overnight in the vacuum oven at 45°C. The reaction yielded 69.6 g (80percent total yield) of 5-amino-2-chloro-isonicotinic acid as a pale yellow solid, which was pure enough by NMR to use in the next reaction. ON (DMSO) 7.99 (1 H, d), 7.45 (1 H, d) MS [M+H] + 173 |
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