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CAS No. : | 37619-24-2 | MDL No. : | MFCD00052747 |
Formula : | C7H9NO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | APHVGKYWHWFAQV-UHFFFAOYSA-N |
M.W : | 139.15 | Pubchem ID : | 142178 |
Synonyms : |
|
Num. heavy atoms : | 10 |
Num. arom. heavy atoms : | 5 |
Fraction Csp3 : | 0.29 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 36.97 |
TPSA : | 31.23 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.87 cm/s |
Log Po/w (iLOGP) : | 2.07 |
Log Po/w (XLOGP3) : | 1.8 |
Log Po/w (WLOGP) : | 0.81 |
Log Po/w (MLOGP) : | 0.37 |
Log Po/w (SILICOS-IT) : | 0.63 |
Consensus Log Po/w : | 1.14 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.07 |
Solubility : | 1.17 mg/ml ; 0.00842 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.07 |
Solubility : | 1.17 mg/ml ; 0.00842 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -1.22 |
Solubility : | 8.42 mg/ml ; 0.0605 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.44 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302 | 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 |
---|---|---|
89% | Stage #1: With sodium hydride In tetrahydrofuran at 0 - 20℃; for 0.5 h; Stage #2: at 20℃; for 17 h; |
To a mixture of methyl- lH-pyrrole-2-carboxylate (10 g, 79.9 mmol) in anhydrous THF (200 mL) was added NaH (3.52 g, 60percent w.t., 87.9 mmol) at 0°C. The resulting mixture was stirred at 20°C for 30 min, then CH3I (13.62 g, 95.9 mmol) was added. The reaction mixture was stirred at 20°C for 17 hrs. The mixture was then poured into an aqueous solution of NH4CI (200 mL). The aqueous layer was extracted with EtOAc (200 mL x 2). The combined organic layers were washed with brine (150 mL), dried (Na2S04), filtered, and concentrated in vacuo. The residue was purified by chromatography (silica, EtOAc/PE = 1/20) to afford methyl 1 -methyl- lH-pyrrole-2- carboxylate (9.88 g, 71 mmol, 89 percent) as a yellow oil. MS (EI+, m/z): 140.1 [M+H]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With aluminum (III) chloride In nitromethane; 1,2-dichloro-ethane at -25℃; for 0.5 h; | To a mixture of methyl- 1 -methyl- lH-pyrrole-2-carboxylate (10 g, 71.86 mmol), AlCb (21.08 g, 158.1 mmol) in 1,2-dichloroethane (100 mL), and MeN02 (100 mL) was added a solution of dichloro(methoxy)methane (8.26 g, 71.86 mmol) at -25°C. The resulting mixture was stirred at -25°C for 0.5 hr. The mixture was then poured into ice (100 mL). The mixture was partitioned between CH2CI2 (100 mL) and H20 (100 mL). The layers were separated. The CH2CI2 layer was dried over Na2S04, filtered, and concentrated in vacuo. The residue was purified by chromatography (silica, EtOAc/PE = 1/1) to afford methyl 4-formyl-l -methyl- lH-pyrrole-2- carboxylate (11.77 g, 70.42 mmol, 98percent) as a yellow solid. MS (EI+, m/z): 168.2 [M+H]+. MR (400 MHz, DMSO-^) δ 9.71 (s, 1H), 7.91 (d, J= 1.8 Hz, 1H), 7.22 (d, J= 1.8 Hz, 1H), 3.92 (s, 3H), 3.78 (s, 3H). NOESY confirmed this structure. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
53% | Stage #1: With n-butyllithium In tetrahydrofuran at -78℃; for 2 h; Inert atmosphere Stage #2: at 20℃; for 16 h; |
To a solution of methyl- 1 -methyl- lH-pyrrole-2-carboxylate (10.0 g, 71.86 mmol) in THF (200 mL) at -78°C was added n-BuLi (31.6 mL, 79.05 mmol) under nitrogen. The mixture was stirred at -78°C for 2 hrs. DMF (10.49 g, 143.72 mmol) was then added and the mixture was stirred for an additional 16 hrs while allowed to warm to rt. The mixture was then quenched with H20 (500 mL) and extracted with EtOAc (200 mL x 3). The combined organic layers were washed with brine, dried over Na2S04, filtered, concentrated, and purified by chromatography (silica, EtOAc/PE = 1/8) to afford methyl 4-formyl- 1 -methyl- lH-pyrrole-2-carboxylate (6.37g, 38.09 mmol, 53percent) as an oil. ESI-MS (EI+, m/z): 168.3 [M+H]+. |
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