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CAS No. : | 182556-72-5 | MDL No. : | MFCD11847315 |
Formula : | C12H10ClNO | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | XZLZQERVHJHMAL-UHFFFAOYSA-N |
M.W : | 219.67 | Pubchem ID : | 53404197 |
Synonyms : |
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Num. heavy atoms : | 15 |
Num. arom. heavy atoms : | 12 |
Fraction Csp3 : | 0.08 |
Num. rotatable bonds : | 3 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 60.23 |
TPSA : | 22.12 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | Yes |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | Yes |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.31 cm/s |
Log Po/w (iLOGP) : | 2.58 |
Log Po/w (XLOGP3) : | 3.28 |
Log Po/w (WLOGP) : | 3.16 |
Log Po/w (MLOGP) : | 2.29 |
Log Po/w (SILICOS-IT) : | 3.49 |
Consensus Log Po/w : | 2.96 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.66 |
Solubility : | 0.0478 mg/ml ; 0.000218 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.42 |
Solubility : | 0.0836 mg/ml ; 0.000381 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -5.31 |
Solubility : | 0.00108 mg/ml ; 0.0000049 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.8 |
Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501 | UN#: | |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | |
GHS Pictogram: |
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* 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 |
---|---|---|
96% | With lithium hexamethyldisilazane In tetrahydrofuran at 65℃; for 0.5 h; | Example 10 ; [Show Image] Synthesis of N4-(4-(H-imidazo[1,2-a]pyridin-7-yloxy)-3-methylphenyl)-N6-(4,4-dimethyl-4,5-dihydrooxazol-2-yl)quinazoline-4,6-diamine Step A: Preparation of 4-(benzyloxy)pyridin-2-amine: To a mixture of 4-(benzyloxy)-2-chloropyridine (1.10 g, 5.01 mmol), Pd2dba3 (46 mg, 0.05 mmol) and 2-(dicyclohexylphosphino)-2',4',6'-tri-propyl-1,1'-biphenyl (57 mg, 0.120 mmol) in THF (10 mL) was added LHMDS (6 mL of 1.0 M solution). After heating to 65 °C for 30 minutes, the mixture was cooled to room temperature and concentrated onto silica gel. The product was eluted with 20:1 ethyl acetate/methanol to isolate a pale gold solid (0.97 g, 96percent). |
82% | Stage #1: With tris-(dibenzylideneacetone)dipalladium(0); lithium hexamethyldisilazane; CyJohnPhos In tetrahydrofuran at 65℃; for 1 h; Inert atmosphere Stage #2: With hydrogenchloride; water In tetrahydrofuran for 0.0833333 h; |
LiHMDS (105.4 mL, 1 M solution in THF, 105.4 mmol) was added to a solution of intermediate 10 ( 19.3 g, 87.9 mmol), Pd2(dba).5 (2.0 g, 2.2 mmol, 0.025 eq.) and 2- dicyclohexylphosphinobiphenyl (2.5 g, 5.2 mmol, 0.06 eq.) in anhydrous THF (90 mL) under a nitrogen atmosphere, the resulting mixture was stirred at 65 °C for 1 h. The reaction was then allowed to cool to room temperature and IN aqueous HC1 was added. Following 5 min of vigorous stirring, the reaction mixture was neutralized with saturated Na2CC"3 and extracted with CH2CI2. The combined organic phases were dried over MgS04 and concentrated under reduced pressure. The crude product was suspended in isopropyl ether and stirred for 15 min at reflux temperature, after which it was allowed to cool to room temperature overnight. The precipitate was filtered off and dried under high vacuum to give intermediate 11 ( 14.7 g, 82percent yield). |
70.2% | Stage #1: With lithium hexamethyldisilazane In tetrahydrofuran at 50℃; for 1.5 h; Stage #2: With hydrogenchloride; water In tetrahydrofuran at 20℃; for 2 h; |
Example 195 3-(5-bromo-2-C4-phenethylthiazol-2-ylamino)pyridin-4-yloxyV5- chloroisonicotinonitrile[00552] Step A: Preparation of ^fbenzyloxVlp yridiα-2-amine: A-(benzyloxy)-2-chloroρyridine (18.6 g, 84.7 mmol), XPHOS (4.04 g5 8.47 mmol), and Pd2dba3 (3.88 g, 4.23 mmol) were mixed in THF (250 mL). LHMDS (93.1 ml, 93.1 mmol) was added and the reaction was heated at 50 0C for 1.5 hours. The solution was cooled and diluted with IN HCl (50 mL) and stirred at ambient temperature for 2 hours. The reaction was concentrated and the residue was extracted with EtOAc. The aqueous layer was basified with saturated K2CO3 and the aqueous layer was extracted with EtOAc. The combined organic layers were dried and concentrated to give the desired product (11.9 g, 70.2percent yield) as a brown solid. |