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CAS No. : | 133972-63-1 | MDL No. : | MFCD09878864 |
Formula : | C10H8N2O2S | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | JVDCBFYWWGXIRC-UHFFFAOYSA-N |
M.W : | 220.25 | Pubchem ID : | 11535888 |
Synonyms : |
|
Num. heavy atoms : | 15 |
Num. arom. heavy atoms : | 11 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 3 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 58.62 |
TPSA : | 90.46 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.73 cm/s |
Log Po/w (iLOGP) : | 1.43 |
Log Po/w (XLOGP3) : | 2.69 |
Log Po/w (WLOGP) : | 2.58 |
Log Po/w (MLOGP) : | 1.16 |
Log Po/w (SILICOS-IT) : | 2.23 |
Consensus Log Po/w : | 2.02 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.56 |
Log S (ESOL) : | -3.24 |
Solubility : | 0.125 mg/ml ; 0.000569 mol/l |
Class : | Soluble |
Log S (Ali) : | -4.24 |
Solubility : | 0.0126 mg/ml ; 0.0000572 mol/l |
Class : | Moderately soluble |
Log S (SILICOS-IT) : | -3.24 |
Solubility : | 0.126 mg/ml ; 0.00057 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.52 |
Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501 | UN#: | |
Hazard Statements: | H302-H312-H315-H319-H332-H335 | Packing Group: | |
GHS Pictogram: |
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* 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 |
---|---|---|
In water at 60℃; pH's from -1.00 to 4.71; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
52% | With sodium hydroxide Ambient temperature; | |
22% | With lithium hydroxide; water In tetrahydrofuran at 60℃; for 12h; | 65B Step 65B: A stirred solution of 65a (120 mg, 0.513 mmol) in a mixture of 1M aq LIOH (2 mL) and THF (2 mL) was heated at 60 °C in a sealed tube for 12 h. The reaction mixture was cooled to room temperature and the aqueous layer was separated, acidified to pH 2.0 and extracted with EtOAc (2 x 20 mL). The combined organic layers were dried (MGS04), filtered and the solvent was removed in vacuo to give 65-1 (25 mg, 22%) as a cream solid which was used without further purification : IH-NMR (300MHZ, DMSO-D6) 8 7.77 (1H, s), 7.47-7. 53 (2H, M), 7.20-7. 28 (2H, M) and 6.96 (1H, dd, J = 7.7, 7.7Hz) ; LC-MS 221.0 (MH+). |
Stage #1: methyl 2-phenylaminothiazole-5-carboxylate With lithium hydroxide In methanol; water at 20 - 50℃; for 3h; Stage #2: With hydrogenchloride In methanol; water | 2-Anilino-1,3-thiazole-5-carboxylic Acid (4-4); Methyl 2-anilino-1,3-thiazole-5-carboxylate (4-3, 0.200 g, 0.854 mmol) was dissolved in 4 mL of 3:1 MeOH/water. Lithium hydroxide hydrate (0.179 g, 4.27 mmol) was added and the reaction was stirred at ambient temperature for 1 hour. The mixture was heated to 50° C. for 2 hours and was then cooled and diluted with water. The solution was adjusted to pH 4 with 1M aqueous HCl. A precipitate formed which was filtered and washed with water. 1H NMR (DMSO-4) δ 12.8 (bs, 1H), 10.7 (s, 1H), 7.6 (d, 2H), 7.4 (t, 2H), 7.0 (t, 1H). MS [M+H]+=221.1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 38 percent / ethanol / 1 h / Heating 2: 52 percent / NaOH / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In DMF (N,N-dimethyl-formamide) for 3h; | 2-Anilino-N-benzyl-1.3-thiazole-5-carboxamide (4-5); 2-Anilino-1,3-thiazole-5-carboxylic acid (4-4, 0.025 g, 0.11 mmol), 1-(3-dimethylaminopropyl)3-ethylcarbodiimide hydrochloride (0.024 g, 0.13 mmol), 1-hydroxy-7-azabenzotriazole (0.016 g, 0.11 mol) and benzylamine (0.014 mL, 0.13 mmol) were dissolved in 1 mL dimethylformamide. After 3 hours the reaction was purified by reverse phase preparative HPLC followed by flash column chromatography to afford the pure title compound. 1H NMR (CD3OD) δ 7.81 (s, 1H), 7.53 (d, 2H, J=8.9 Hz), 7.35-7.22 (m, 7H), 7.04 (t, 1H, J=7.3 Hz), 4.50 (s, 2H). MS [M+H]+=310.0. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In DMF (N,N-dimethyl-formamide) | 2-Anilino-N,N-dimethyl-1,3-thiazole-5-carboxamide (4-6); 2-Anilino-1,3-thiazole-5-carboxylic acid (4-4, 0.025 g, 0.11 mmol), 1-(3-dimethylaminopropyl)3-ethylcarbodiimide hydrochloride (0.024 g, 0.13 mmol), 1-hydroxy-7-azabenzotriazole (0.016 g, 0.11 mol), dimethylamine hydrochloride (0.010 g, 0.10 mmol) and N,N-diisopropylethylamine (0.016 g, 0.13 mmol) were dissolved in 1 mL dimethylformamide. The reaction was stirred overnight and was then concentrated in vacuo. The residue was purified by flash column chromatography (gradient elution using 50% to 80% ethyl acetate in dichloromethane) to afford the pure title compound. 1H NMR (CDCl3) δ 7.84 (bs, 1H), 7.58 (s, 1H), 7.43-7.34 (m, 4H), 7.17-7.10 (m, 1H), 3.2 (s, 6H). MS [M+H]+=248.1. |