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CAS No. : | 1040682-92-5 | MDL No. : | MFCD09965907 |
Formula : | C9H8N2O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | VLFGZDBQUVCFJQ-UHFFFAOYSA-N |
M.W : | 176.17 | Pubchem ID : | 26076445 |
Synonyms : |
|
Num. heavy atoms : | 13 |
Num. arom. heavy atoms : | 9 |
Fraction Csp3 : | 0.11 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 47.37 |
TPSA : | 54.98 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) : | -6.54 cm/s |
Log Po/w (iLOGP) : | 1.57 |
Log Po/w (XLOGP3) : | 1.17 |
Log Po/w (WLOGP) : | 1.35 |
Log Po/w (MLOGP) : | 0.23 |
Log Po/w (SILICOS-IT) : | 1.84 |
Consensus Log Po/w : | 1.23 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.05 |
Solubility : | 1.57 mg/ml ; 0.00892 mol/l |
Class : | Soluble |
Log S (Ali) : | -1.92 |
Solubility : | 2.12 mg/ml ; 0.012 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -2.98 |
Solubility : | 0.183 mg/ml ; 0.00104 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.69 |
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 |
---|---|---|
25% | With N-chloro-succinimide; In N,N-dimethyl-formamide; at 20℃; for 18h; | EXAMPLE 11 Synthesis of 3,6-dichloro-4-methoxycarbonyl-1 H-pyrrolo[3,2- c]pyridine (Compound 22-132)1 1.1 Preparation of 3-chloro-4-methoxycarbonyl-1 H-pyrrolo[3,2-c]pyridineA solution of 4-methoxycarbonyl-1 H-pyrrolo[3,2-c]pyridine (0.25 g, 1.4 mmol) and N- chlorosuccinimide (0.23 g, 1.7 mmol) in dimethylformamide (5 ml) was stirred at ambient temperature for 18 hours, then poured into water. The resulting mixture was extracted with diethyl ether and the combined organic phases evaporated under reduced pressure to provide a yellow solid. This was purified using a FractionLynx hplc, to provide 3- chloro-4-methoxycarbonyl-l H-pyrrolo[3,2-c]pyridine as a solid (74 mg, 25%).Characterising data for the compound are as follows:1H NMR (400 MHz, CD3OD) delta 8.22 (1 H, d), 7.57 (1 H, d), 7.56 (1 H, s), 4.60 (1 H, br s), 4.02 (3H, s) ppm |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | A solution of <strong>[1040682-92-5]methyl 1H-pyrrolo[3,2-c]pyridine-4-carboxylate</strong> (501.7 mg, 2.85 mmol; commercially available from, for example, Matrix Scientific) in DMF (10 mL) was cooled to approx. 0 C in an ice bath under nitrogen. To this stirring mixture was added sodium hydride (6O% dispersion in mineral oil, 179.1 mg, 4.48 mmol) portionwise to afford a bright yellow solution. This was stirred at 0 C forapprox. 10 mm, after which 4-toluenesulfonyl chloride (700.1 mg, 3.67 mmol) was added. The mixture was allowed to warm to rt while stirring and was stirred for a further 2.25 h. To the reaction mixture was added water (10 mL) and it was stirred for a further 5 mm. To this mixture was added sat. aqueous lithium chloride (25 mL) and water (25 mL). The resulting cloudy yellow solution was extracted with ethyl acetate (3 x 50 mL). The organic phases were combined and filtered through acartridge fitted with a hydrophobic frit. The filtrate was evaporated in vacuo to give a light yellow solid; methyl 1-tosyl-1H-pyrrolo[3,2-c]pyridine-4-carboxylate (837.9 mg, 2.54 mmol, 89 % yield).LCMS (2 mm high pH) Rt = 1.07 mi m/z= 331 for [MH]1H NMR (400 MHz, CDCI3) O ppm 8.62 (d, J=5.4 Hz, 1 H) 8.09 (dd, J=5.6, 0.7 Hz, 1 H) 7.79 (d, J=8.3 Hz, 2 H) 7.73 (d, J=3.7 Hz, 1 H) 7.42 (d, J=3.2 Hz, 1 H) 7.24 - 7.31 (m, 2 H) 4.04 (5, 3 H)2.37 (5, 3 H) |
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