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CAS No. : | 3284-47-7 | MDL No. : | MFCD01006747 |
Formula : | C8H11NO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | FGILMAYWLMWCQA-UHFFFAOYSA-N |
M.W : | 153.18 | Pubchem ID : | 5324582 |
Synonyms : |
|
Num. heavy atoms : | 11 |
Num. arom. heavy atoms : | 5 |
Fraction Csp3 : | 0.38 |
Num. rotatable bonds : | 3 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 41.85 |
TPSA : | 42.09 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) : | -6.08 cm/s |
Log Po/w (iLOGP) : | 1.96 |
Log Po/w (XLOGP3) : | 1.63 |
Log Po/w (WLOGP) : | 1.5 |
Log Po/w (MLOGP) : | 0.71 |
Log Po/w (SILICOS-IT) : | 2.01 |
Consensus Log Po/w : | 1.56 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.95 |
Solubility : | 1.7 mg/ml ; 0.0111 mol/l |
Class : | Very soluble |
Log S (Ali) : | -2.13 |
Solubility : | 1.14 mg/ml ; 0.00747 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -2.46 |
Solubility : | 0.532 mg/ml ; 0.00348 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.86 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H332-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 |
---|---|---|
83% | With sodium hydroxide In ethanol; water at 20℃; | 10.0 g (65.3 mmol) of ethyl 3-methyl-1 H-pyrrole-2-carboxylate (purchased from Astatech®, cat. no. 59362) was dissolved in 200 ml of ethanol. 150 ml of a 2 M solution of sodium hydroxide were added and the resulting solution was stirred at room temperature overnight. The organics were removed under reduced pressure and the resulting aqueous solution was neutralized with a 5 M solution of hydrochloric acid. A white solid precipitated, which was filtered, washed with water and dried in the oven. 6.80 g (83percent yield) of the title compound were obtained. LRMS (m/z): 126 (M+1 )+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With sodium ethanolate In ethanol at 20℃; for 5 h; | 3-Alkyl pyrrole derivatives were prepared according to the procedure outlined in Scheme 1. Glycine ethyl ester, 5, was treated with p- toluenesulfonyl chloride (Ts-Cl) to give 6, which upon treatment with 4- diethylaminobutan-2-one in the presence of f-BuOK gave 7. Dehydration with POCl3 yielded the dihydropyrrole derivative 8. Elimination in the presence of sodium ethoxide generated pyrrole derivative 9. The pyrrole nitrogen was deprotonated with sodium hydride and alkylated to give 10. The ester was hydrolyzed with aqueous KOH in MeOH and then the corresponding acid 11 was converted to amides (81), (82), and (83) using EDCI. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuranHeating / reflux | Pyrroline 83 (8.80 g, 28.48 mmol) was dissolved in THF (70 mL). DBU (9.78 mL, 65.50 mmol) was added dropwise and the resulting solution stirred under reflux overnight. The mixture was cooled to room temperature, diluted with ether and washed with 5percent aq. HCl, 5percent sodium bicarbonate solution and water. The organic layer was dried over sodium sulfate, filtered and evaporated under reduced pressure to give the crude solid 84 (4.30 g, 98percent). 1H-NMR (400 MHz, CDCl3): δ 1.37 (t, 3H), 2.35 (s, 3H), 4.31 (q, 2H), 6.08 (d, 1H), 6.81 (d, 1H), 8.90 (s broad, 1H) ppm. 13C-NMR (100 MHz, CDCl3): δ 12.76, 14.53, 59.96, 112.58, 119.35, 121.53, 127.96, 162.01 ppm. DEPT (100 MHz, CDCl3): CH3 carbons: 12.76, 14.53; CH2 carbons: 59.96; CH carbons: 112.58, 121.53 ppm. LC/MS: 90.74percent, m/z=153. |
6.86 g | With sodium ethanolate In ethanol | mixture of Compound IV (16.70 g) and a solution of sodium ethoxide in ethanol (20percent, 160 mL) was stirred overnight. To the reaction solution was added saturated aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate. The organic layer was dried over sodium sulfate and concentrated under reduced pressure, and then the residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate = 4/1) to give Compound V (6.86 g). |
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