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CAS No. : | 130473-26-6 | MDL No. : | MFCD10697530 |
Formula : | C8H6N2O | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | SHTJIHCOCNIHLP-UHFFFAOYSA-N |
M.W : | 146.15 | Pubchem ID : | 14644283 |
Synonyms : |
|
Num. heavy atoms : | 11 |
Num. arom. heavy atoms : | 9 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 41.48 |
TPSA : | 45.75 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) : | -6.64 cm/s |
Log Po/w (iLOGP) : | 0.64 |
Log Po/w (XLOGP3) : | 0.77 |
Log Po/w (WLOGP) : | 1.38 |
Log Po/w (MLOGP) : | -0.32 |
Log Po/w (SILICOS-IT) : | 2.17 |
Consensus Log Po/w : | 0.93 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.77 |
Solubility : | 2.48 mg/ml ; 0.017 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.31 |
Solubility : | 7.14 mg/ml ; 0.0489 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -2.84 |
Solubility : | 0.213 mg/ml ; 0.00146 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 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: | 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 |
---|---|---|
81% | With water; toluene-4-sulfonic acid In acetonitrile for 5 h; Heating / reflux | C173 (800 mg, 4.21 mmol) is dissolved in 44 mL 10percent aqueous acetonitrile. p-Toluene sulfonic acid (630 mg, 3.3 mmol) is added, and the mixture is heated to reflux for 5 h. The mixture is cooled to rt, is concentrated in vacuo, and the resultant residue is diluted with 15 mL saturated NaHCO3. A pale yellow solid is collected, washed with water, and is dried to afford 1H-PYRROLO [2,3-c] PYRIDINE-5-CARBALDEHYDE (C174) (81percent yield). HRMS (FAB) calculated for CGH6N2O+H : 147.0558, found 147.0564 (M+H) +. |
81% | With toluene-4-sulfonic acid In acetonitrile | 5-(1,3-Dioxolan-2-yl)-1H-pyrrolo[2,3-c]pyridine (800 mg, 4.21 mmol) is dissolved in 44 ml 10percent aqueous acetonitrile in a flask. The solution is treated with p-toluene sulfonic acid (630 mg, 3.3 mmol), and the mixture is heated to reflux for 5 h. The mixture is cooled to rt, is concentrated in vacuo, and the resultant residue is diluted with 15 ml saturated NaHCO3. The pale yellow solid is collected, washed with water, and is dried to give 500 mg (81percent) of 1H-pyrrolo[2,3-c]pyridine-5-carbaldehyde. HRMS (FAB) calcd for C8H6N2O+H: 147.0558, found 147.0564 (M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67% | With sodium hydroxide; dihydrogen peroxide In formic acid; water | C174 (500 mg, 3.42 mmol) is dissolved in 1.5 mL formic acid. The solution is cooled in an ice bath, 30percent aqueous hydrogen peroxide (722 μL, 6.8 mmol) is added drop-wise, and the reaction is stirred 1 h in an ice bath, and allowed to stand overnight at 5° C. The mixture is diluted with H2O, the solid is collected, washed with H2O and is dried to give 522 mg of an off-white solid. The formate salt is added to 7 mL H2O, 3 mL 2N NaOH is added, and the pH is adjusted to 3 with 5percent aqueous HCl. The precipitate is collected and is dried to afford 1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid (C176) (67percent yield). HRMS (FAB) calculated for C8H6N2O2+H: 163.0508, found 163.0507 (M+H). Example 23(i) can be obtained by coupling either exo-[2.2.1]-3-Amine or endo-[2.2.1]-3-Amine with C176. |
67% | With sodium hydroxide; dihydrogen peroxide In formic acid; water | C174 (500 mg, 3.42 mmol) is dissolved in 1.5 mL formic acid. The solution is cooled to in an ice bath, 30percent aqueous hydrogen peroxide (722 μL, 6.8 mmol) is added drop-wise, and the reaction is stirred 1 h in an ice bath, and allowed to stand overnight at 5° C. The mixture is diluted with water, the solid is collected, washed with water and is dried to give 522 mg of an off-white solid. The formate salt is added to 7 mL water, 3 mL 2N NaOH is added, and the pH is adjusted to 3 with 5percent aqueous HCl. The precipitate is collected and is dried to afford 1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid (C176) (67percent yield). HRMS (FAB) calculated for C8H6N2O2+H: 163.0508, found 163.0507 (M+H)+. |
67% | Stage #1: With dihydrogen peroxide In formic acid; water at 5℃; Stage #2: With sodium hydroxide In water Stage #3: With hydrogenchloride In water |
C174 (500 mg, 3.42 mmol) is dissolved in 1.5 mL formic acid. The solution is cooled to in an ice bath, 30percent aqueous hydrogen peroxide (722 RL, 6.8 mmol) is added drop-wise, and the reaction is stirred 1 h in an ice bath, and allowed to stand overnight at 5C. The mixture is diluted with water, the solid is collected, washed with water and is dried to give 522 mg of an off-white solid. The formate salt is added to 7 mL water, 3 mL 2N NAOH is added, and the pH is adjusted to 3 with 5percent aqueous HC1. The precipitate is collected and is dried to afford 1H-pyrrolo [2,3-c] pyridine-5- carboxylic acid (C176 (67percent yield). HRMS (FAB) calculated for CGH6N202+H : 163.0508, found 163.0507 (M+H) +. |
67% | With dihydrogen peroxide In formic acid; water | 1H-Pyrrolo[2,3-c]pyridine-5-carbaldehyde (500 mg, 3.42 mmol) is dissolved in 1.5 ml formic acid. The solution is cooled in an ice bath, is treated drop-wise with 30percent aqueous hydrogen peroxide (722 μL, 6.8 mmol), is stirred 1 h in an ice bath, and allow to stand overnight at 5° C. The mixture is diluted with water, the solid is collected, washed with water and is dried to give 522 mg of an off-white solid. The formate salt is combined with 7 ml water, is diluted with 3 ml 2N NaOH, and the pH is adjusted to 3 with 5percent aqueous HCl. The precipitate is collected and is dried to give 370 mg (67percent) of 1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid. HRMS (FAB) calcd for C8H6N2O2+H: 163.0508, found 163.0507 (M+H)+. |
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