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CAS No. : | 61323-26-0 | MDL No. : | MFCD18427704 |
Formula : | C7H9NO2S | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | SNOLCJGSEPTCMD-UHFFFAOYSA-N |
M.W : | 171.22 | Pubchem ID : | 12300671 |
Synonyms : |
|
Num. heavy atoms : | 11 |
Num. arom. heavy atoms : | 5 |
Fraction Csp3 : | 0.43 |
Num. rotatable bonds : | 3 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 43.17 |
TPSA : | 67.43 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) : | -5.99 cm/s |
Log Po/w (iLOGP) : | 2.31 |
Log Po/w (XLOGP3) : | 1.91 |
Log Po/w (WLOGP) : | 1.63 |
Log Po/w (MLOGP) : | 0.37 |
Log Po/w (SILICOS-IT) : | 2.64 |
Consensus Log Po/w : | 1.77 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.24 |
Solubility : | 0.978 mg/ml ; 0.00571 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.95 |
Solubility : | 0.192 mg/ml ; 0.00112 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -2.16 |
Solubility : | 1.19 mg/ml ; 0.00697 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.6 |
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 |
---|---|---|
68% | With Isovaleronitrile In tetrahydrofuranReflux | In a 3-neck round bottom flask mix 2-amino-5-methyl-thiazole-4-carboxylic acid ethyl ester (62.9 g, 338 mmol) and THF (630 mL). Heat to reflux and treat the reaction mixture with isoamyl nitrile (52.6 g, 60.1 mL, 449 mmol) dropwise. Upon completion of the addition, stir the reaction at reflux for 1 h, then concentrate the reaction mixture by rotavap (hi-vac) to give 70 g crude product as a thick orange oil. Purify on silica gel (400 g, 20-45percent EtOAc/hexanes) to afford 39.47 g (68percent) of the title compound as a yellow solid. LC-ES/MS m/z 172 (M+1), TR=1.5 min. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
54% | With diisobutylaluminium hydride In tetrahydrofuran; toluene at -78℃; for 0.5 h; Inert atmosphere | Step 1: 5-Methylthiazole-4-carbaldehyde. [00670] To a solution of ethyl 5-methylthiazole-4-carboxylate (794 mg, 5.05 mmol) in THF (21.6 mL) was added dropwise 1.0 M of DIBAL-H in toluene (5.56 mL, 5.56 mmol) under an atmosphere of argon at -78 °C and the reaction was stirred for 30 min. The reaction was quenched with water ( 12.4 mL) at -78 °C. The reaction was warmed to rt. The reaction was poured into 300 mL of saturated Rochelle salt in water and diluted with EtOAc. The layers were stirred together for 1 hour. The layers were separated and the aqueous layer was extracted with EtOAc (x3). The combined organics were washed with brine, dried over Na2S04, filtered and concentrated in vacuo. The residue was purified by ISCO column chromatography ( 10percent EtOAc in DCM as eluent) to give 642 mg (54 percent) of the title compound as yellow oil. NMR (400 MHz, Chloroform-if) δ 10.22 (s, 1 H), 8.62 (s, 1H), 2.83 (s, 3H). |
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