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CAS No. : | 35570-68-4 | MDL No. : | MFCD14706178 |
Formula : | C6H3ClN2O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | ZWGWZXKNFDGBJP-UHFFFAOYSA-N |
M.W : | 170.55 | Pubchem ID : | 13614459 |
Synonyms : |
|
Num. heavy atoms : | 11 |
Num. arom. heavy atoms : | 9 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 39.64 |
TPSA : | 58.89 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.61 cm/s |
Log Po/w (iLOGP) : | 1.28 |
Log Po/w (XLOGP3) : | 1.03 |
Log Po/w (WLOGP) : | 1.17 |
Log Po/w (MLOGP) : | 0.66 |
Log Po/w (SILICOS-IT) : | 2.22 |
Consensus Log Po/w : | 1.27 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.15 |
Solubility : | 1.2 mg/ml ; 0.00705 mol/l |
Class : | Soluble |
Log S (Ali) : | -1.86 |
Solubility : | 2.37 mg/ml ; 0.0139 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -3.06 |
Solubility : | 0.149 mg/ml ; 0.000873 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.32 |
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 |
---|---|---|
80% | at 130℃; for 16 h; | A suspension of 6-chlorooxazolo[4,5-b]pyridin-2(3H)-one (6.Og, 35.3mmol) in 10percent NaOH solution (200mL) was stirred at 130 00 for 16h. TLC showed the reaction to be complete. The reaction mixture was cooled to rt , neutralized with 6.0 N HCI and extracted with EtOAc (3x200mL). The organic layer was washed with brine (200mL), dried (Na2SO4), filtered and concentrated under reduced pressure to afford 2-amino-5-chloropyridin-3-ol as a brown solid. Yield: 4.Og (80percent); 1H NMR (400 MHz, DMSO-d6): 10.03 (bs, 1H), 7.41 (d, J= 2.1 Hz, 1H), 6.82 (d, J= 2.1 Hz, 1H), 5.68 (bs, 2H); MS (ESl+) for CHNOS m/z 145.13 [M+H]. |
420 g | for 10 h; Reflux | Example 2 To a 50L single-neck round flask with magnetic stirrer was added sodium hydroxide (355 g, 8.883 mol) and water (3.5mL). After all sodium hydroxide was dissolved, the obtained 6-chlorooxazole[4,5-b] pyridine-2(3H)-one (3.14 g, 0.018 mol) was added to the reaction flask and a reflux condenser was added in the reaction flask. The reaction mixture was heated under reflux for 10 hours. TLC and GC analysis indicated the reaction was complete. With 12mol / L hydrochloric acid, the reaction mixture was adjusted to pH 8 (with a lot of precipitate formed). Afterwhich it was filtered and the cake was washed with water (400 ml). Drying obtained the product 2-amino-3-hydroxy-5-chloropyridine 420 g, yield 98percent, purity 97.9percent (GC). Melting point 197°C ~ 202°C (literature 198°C ~ 201°C). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With N-chloro-succinimide In N,N-dimethyl-formamide at 20 - 40℃; Autoclave; Large scale | DMF (9 L) was added to a 100 L autoclave.Start the mechanical stirrer and add2,3-dihydropyrido [2, 3-d] [1,3] oxazol-2-one(10 kg).The 2,3-dihydropyrido [2,3-d] [1,3] oxazol-2-one was completely dissolved by stirring.N-chlorosuccinimide (12.16 kg)Was dissolved in DMF (30 L).And then slowly dropping N-chlorosuccinimide into the reactor,Control the reaction temperature does not exceed 40 (If necessary, use a circulating condensate pump to cool).After the dropwise addition, the mixture was stirred overnight at room temperature.The reaction was followed by TLC and GC.After completion of the reaction, 39 L of water was slowly added under cooling.The reaction mixture was stirred for 60 minutes and filtered.The filter cake was washed twice with water and dried in vacuo to give a crude product of 11.8 kg. The crude product was recrystallized from dichloromethane and ethyl acetate to give pure product6-chloroxazole [4,5-b] pyridine-2 (3H) -one(11.1 kg),Yield 89percent |
81% | With N-chloro-succinimide In N,N-dimethyl-formamide at 20 - 40℃; | Example 2 DMF was added to a 10L three-neck round bottom flask (2000mL) with reflux condenser on each neck. Oxazole [4,5-b]pyridine-2(3H)-one (497g) was added with mechanical stirring until it was dissolved. N- chlorosuccinimide (608g) was dissolved in DMF (2500mL). Transferred to a pressure-equalizing dropping funnel, N-chlorosuccinimide was slowly added dropwise to the reaction flask, the reaction temperature is controlled not to exceed 40°C (cooling with ice-water if necessary). Afterwhich, the ice bath was removed, then stirred at room temperature overnight. The reaction was monitored by TLC and GC. After completion of the reaction, 4000mL water was slowly added under cooling with ice water. The reaction mixture was stirred for 30 minutes and filtered. The filter cake was washed twice with water and dried under vacuum to give crude 530g. The crude product was recrystallized from ethyl acetate and methylene chloride to give pure product 6-chlorooxazole[4,5-b]pyridine-2(3H)-one (505g), yield 81percent, purity 99.1percent (GC) . Melting point 184°C ~ 187°C (literature 183°C ~ 186°C). |
55% | With N-chloro-succinimide In acetonitrile at 90℃; for 2 h; | To a solution of oxazolo[4,5-b]pyridin-2(3H)-one (5.Og, 36.7mmol) was added Nchlorosuccinimide (5.Og, 45.8mmol) at rt. The resulting reaction mixture was stirred at 90 °C for 2h. TLC showed the reaction to be complete. The solvent was removed under reduced pressure and the residue was diluted with H20 (lOOmL) and extracted with EtOAc (3xlOOmL). The organic layer was washed with H20 (lOOmL), dried (Na2504), filtered and concentrated under reduced pressure to 6- chlorooxazolo[4,5-b]pyridin-2(3H)-one as a brown solid. Yield: 5.Og (55percent); 1H NMR (400 MHz, DMSO-d6): 12.88 (bs, 1H), 8.08 (d, J= 1.8 Hz, 1H), 7.91 (d, J= 1.8 Hz, 1H); MS (ESl+) for CHNOS m/z 170.98 [M+H]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With pyridine In (2S)-N-methyl-1-phenylpropan-2-amine hydrate; chloroform | Example 6 Phosgene is introduced at 40°-50° C., after the addition of 20 parts of pyridine, into a solution of 10 parts of 2-amino-3-hydroxy-5-chloropyridine in 200 parts of chloroform, and stirring is maintained for one hour at room temperature; the chloroform and the pyridine are evaporated off in a water-jet vacuum, and ice-water is added to the residue. The precipitate is filtered off and dried at 40°-50° C. in vacuo. There are obtained 10 parts of 6-chloro-oxazolo[4,5-b]pyridin-2-(3H)-one (85percent of theory), m.p. 184°-186° C. |
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