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CAS No. : | 19017-52-8 | MDL No. : | MFCD00152035 |
Formula : | C11H10ClNO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | OAIODEZFMSXHFQ-UHFFFAOYSA-N |
M.W : | 223.66 | Pubchem ID : | 2068157 |
Synonyms : |
|
Num. heavy atoms : | 15 |
Num. arom. heavy atoms : | 9 |
Fraction Csp3 : | 0.18 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 59.82 |
TPSA : | 53.09 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) : | -5.86 cm/s |
Log Po/w (iLOGP) : | 1.45 |
Log Po/w (XLOGP3) : | 2.54 |
Log Po/w (WLOGP) : | 2.76 |
Log Po/w (MLOGP) : | 1.95 |
Log Po/w (SILICOS-IT) : | 3.32 |
Consensus Log Po/w : | 2.4 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.85 |
Log S (ESOL) : | -3.14 |
Solubility : | 0.162 mg/ml ; 0.000726 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.3 |
Solubility : | 0.112 mg/ml ; 0.000499 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -4.07 |
Solubility : | 0.0189 mg/ml ; 0.0000845 mol/l |
Class : | Moderately soluble |
PAINS : | 1.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.8 |
Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P280-P301+P312-P302+P352-P305+P351+P338 | UN#: | |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | |
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 |
---|---|---|
With zinc(II) chloride Erwaermen des Reaktionsprodukts mit methanol. KOH; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sulfuric acid for 1h; Heating; Yield given; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride; N-benzyl-trimethylammonium hydroxide 1.) THF, reflux, 10 h, 2.) ethanol, room temp., 1 h; Multistep reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | With 2-chloro-1-methylpyrimidinium iodide; triethylamine In dichloromethane for 2h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With water; sodium hydroxide In ethanol at 20℃; for 3h; | |
With sodium hydroxide In ethanol for 1h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
64% | R.84 2-(5-chloro-2-methyl-1H-indol-3-yl)acetic acid Reference Example 84 2-(5-chloro-2-methyl-1H-indol-3-yl)acetic acid Reaction was conducted in the same manner as Reference Example 81, except that 4-chlorophenylhydrazine hydrochloride was used instead of 4-trifluoromethoxyphenylhydrazine hydrochloride, to obtain the title compound (64% yield). The NMR data for the obtained compound were as follows. NMR: (300 MHz, DMSO-d6) δ: 2.31 (3H,s), 3.55 (2H,s), 6.98 (1H,dd), 7.26 (1H,d), 7.39 (1H,d), 11.05 (1H,s), 11.8-12.2 (1H,m) | |
4-(2-Methyl-1,3-dioxolanyl-2)-6-chlor-2-oxo-1,2,3,4-Tetrahydro-chinolin. konz. HCl, (Siedetemp., 15min); | ||
(5-Chlor-2-methyl-1-acetyl-indolyl-3)-essigsaeure-ethylester (IV), NaOH, sd. wss. Me.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 1.) CH3COONa, 1 M CH3COOH, 2.) H2SO4 / 2.) EtOH, reflux, 3 h 2: 6 M NaOH / ethanol / 1 h / Heating | ||
Multi-step reaction with 2 steps 1.1: sodium acetate / acetic acid / 70 °C 1.2: Reflux 2.1: sodium hydroxide; water / ethanol / 3 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 1.) CH3COONa, 1 M CH3COOH, 2.) H2SO4 / 2.) EtOH, reflux, 3 h 2: 6 M NaOH / ethanol / 1 h / Heating | ||
Multi-step reaction with 2 steps 2: ZnCl2 / Erwaermen des Reaktionsprodukts mit methanol. KOH | ||
Multi-step reaction with 2 steps 1.1: sodium acetate / acetic acid / 70 °C 1.2: Reflux 2.1: sodium hydroxide; water / ethanol / 3 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: conc.H2SO4 / 1 h / Heating 2: LiAlH4 / tetrahydrofuran / 2 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: conc.H2SO4 / 1 h / Heating 2: LiAlH4 / tetrahydrofuran / 2 h / Heating 3: SOCl2 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: conc.H2SO4 / 1 h / Heating 2: LiAlH4 / tetrahydrofuran / 2 h / Heating 3: SOCl2 4: triethylamine / benzene |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere 1.2: 20 °C 2.1: water; lithium hydroxide / tetrahydrofuran; methanol / 2 h / 20 °C | ||
Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere 1.2: -78 - 20 °C / Inert atmosphere 1.3: 24 h / 20 °C / Inert atmosphere 2.1: water; lithium hydroxide / tetrahydrofuran; methanol / 2 h / 20 °C | ||
Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 1.2: Inert atmosphere 1.3: 19 h / 20 °C 2.1: lithium hydroxide / 1,4-dioxane; water / 1.5 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: sodium acetate / toluene / 16 h / 200 °C / Inert atmosphere 2: hydrazine / isopropyl alcohol / 16 h / Inert atmosphere; Reflux 3: potassium carbonate / N,N-dimethyl-formamide / 16 h / 85 °C 4: water; lithium hydroxide / tetrahydrofuran; methanol / 2 h / 20 °C | ||
Multi-step reaction with 5 steps 1: sodium acetate / 16 h / 200 °C / Inert atmosphere; Sonication 2: hydrazine / isopropyl alcohol / 16 h / Inert atmosphere; Reflux 3: potassium carbonate / N,N-dimethyl-formamide / 16 h / 85 °C / Inert atmosphere 4: potassium carbonate / N,N-dimethyl-formamide / 16 h / Inert atmosphere; Heating 5: water; lithium hydroxide / tetrahydrofuran; methanol / 2 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: sodium acetate / toluene / 16 h / 200 °C / Inert atmosphere 2: hydrazine / isopropyl alcohol / 16 h / Inert atmosphere; Reflux | ||
Multi-step reaction with 2 steps 1: sodium acetate / 16 h / 200 °C / Inert atmosphere; Sonication 2: hydrazine / isopropyl alcohol / 16 h / Inert atmosphere; Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: sodium acetate / toluene / 16 h / 200 °C / Inert atmosphere 2: hydrazine / isopropyl alcohol / 16 h / Inert atmosphere; Reflux 3: potassium carbonate / N,N-dimethyl-formamide / 16 h / 85 °C | ||
Multi-step reaction with 3 steps 1: sodium acetate / 16 h / 200 °C / Inert atmosphere; Sonication 2: hydrazine / isopropyl alcohol / 16 h / Inert atmosphere; Reflux 3: potassium carbonate / N,N-dimethyl-formamide / 16 h / 85 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: sodium acetate / toluene / 16 h / 200 °C / Inert atmosphere 2.1: hydrazine / isopropyl alcohol / 16 h / Inert atmosphere; Reflux 3.1: potassium carbonate / N,N-dimethyl-formamide / 16 h / 85 °C 4.1: potassium carbonate / N,N-dimethyl-formamide / 0.27 h / 85 °C / Inert atmosphere 4.2: 20 °C | ||
Multi-step reaction with 4 steps 1: sodium acetate / 16 h / 200 °C / Inert atmosphere; Sonication 2: hydrazine / isopropyl alcohol / 16 h / Inert atmosphere; Reflux 3: potassium carbonate / N,N-dimethyl-formamide / 16 h / 85 °C / Inert atmosphere 4: potassium carbonate / N,N-dimethyl-formamide / 16 h / Inert atmosphere; Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | With sodium acetate In toluene at 200℃; for 16h; Inert atmosphere; | 84.3 To a 100 mL round bottom flask under an atmosphere of nitrogen added intermediate 115, 2-(5-chloro-2-methyl-1H-indol-3-yl)acetic acid (3.59 g, 16.13 mmol, 1.0 equiv), phthalic anhydride (2.39 g, 16.13 mmol, 1.0 equiv) and sodium acetate (7.94 g, 96.81 mmol, 6.0 equiv). 40 mL of toluene was added, and the suspension was sonicated for 5 minutes. The toluene was then removed in vacuo and the resulting powder heated neat to 200° C. for 16 hours. After cooling to room temperature, the resulting brown solid was washed with 1.2N HCl and water and dried. The resulting material was carried on crude (4.08 g, 77%). |
77% | With sodium acetate at 200℃; for 16h; Inert atmosphere; Sonication; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | Stage #1: methyl 2-(5-chloro-2-methyl-1H-indol-3-yl)acetate With water; lithium hydroxide In tetrahydrofuran; methanol at 20℃; for 2h; Stage #2: With hydrogenchloride In tetrahydrofuran; methanol; water | 84.2 To a 250 mL round bottom flask was added intermediate 114, methyl 2-(5-chloro-2-methyl-1H-indol-3-yl)acetate (4.53 g, 19.07 mmol, 1.0 equiv) and 50 mL THF. To this was added a solution of Lithium hydroxide (2.28 g, 95.37 mmol, 5.0 equiv) in 25 mL water. To the resulting biphasic mixture was added methanol dropwise until a single layer formed. The resulting solution was stirred for 2 hours at room temperature. It was then poured into 1.2 N HCl(aq) and the aqueous layer was extracted with three 100 mL portions of ethyl acetate. The combined organic layers were washed with water and brine and dried over magnesium sulfate. Filtration and removal of solvent in vacuo gave the desired product (3.59 g, 84%). 1H NMR (400 MHz, DMSO-d6) δ 2.32 (s, 3H) 3.56 (s, 2H) 6.98 (dd, J=8.5, 2.1 Hz, 1H) 7.25 (d, J=8.6 Hz, 1H) 7.40 (d, J=2.0 Hz, 1H) 11.05 (s, 1H) 12.12 (s, 1H). |
84% | With water; lithium hydroxide In tetrahydrofuran; methanol at 20℃; for 2h; | |
With lithium hydroxide In 1,4-dioxane; water for 1.5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 6 h / 140 °C 2: ethanol / 8 h / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 6 h / 140 °C 2: ethanol / 8 h / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 6 h / 140 °C 2: ethanol / 8 h / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 6 h / 140 °C 2: ethanol / 8 h / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 6 h / 140 °C 2: ethanol / 8 h / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 6 h / 140 °C 2: ethanol / 8 h / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 6 h / 140 °C 2: ethanol / 8 h / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 6 h / 140 °C 2: ethanol / 8 h / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | at 140℃; for 6h; | 2.1.2. General Procedure for the Synthesis of 4-amino-5-mercapto-3-[(5-substituted-2-methyl-1H-indol-3-yl)-methyl]-1,2,4-triazoles (2a-c) General procedure: 4-Amino-5-mercapto-3-[(5-substituted-2-methyl-1H-indol-3-yl)methyl]-1,2,4-triazoles (2a-c) were synthesized by the fusion reaction of 5-substituted-2-methylindole-3-acetic acids 1a-c (50 mmol) with thiocarbohydrazide (50 mmol) in oil bath at 140°C for 6 hours. The solid formed was neutralized by saturated sodium bicarbonate solution. The crude triazole was then purified by recrystallization using hot ethanol[38]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79 mg | With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 17h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / N,N-dimethyl-formamide / 0 °C 1.2: 0 - 20 °C 2.1: lithium aluminium tetrahydride / tetrahydrofuran / 48 h / 0 - 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / N,N-dimethyl-formamide / 0 °C 1.2: 0 - 20 °C 2.1: lithium aluminium tetrahydride / tetrahydrofuran / 48 h / 0 - 20 °C / Inert atmosphere 3.1: sodium hydride / N,N-dimethyl-formamide / 0 °C / Inert atmosphere 3.2: 12 h / 20 - 50 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / N,N-dimethyl-formamide / 0 °C 1.2: 0 - 20 °C 2.1: lithium aluminium tetrahydride / tetrahydrofuran / 48 h / 0 - 20 °C / Inert atmosphere 3.1: sodium hydride / N,N-dimethyl-formamide / 0 °C / Inert atmosphere 3.2: 12 h / 20 - 50 °C / Inert atmosphere 4.1: trifluoroacetic acid / dichloromethane / 16 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / N,N-dimethyl-formamide / 0 °C 1.2: 0 - 20 °C 2.1: lithium aluminium tetrahydride / tetrahydrofuran / 48 h / 0 - 20 °C / Inert atmosphere 3.1: N,N,N,N,N,N-hexamethylphosphoric triamide; potassium hexamethylsilazane / tetrahydrofuran; toluene / 0.5 h / -78 - -22 °C / Inert atmosphere 3.2: -78 - 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / N,N-dimethyl-formamide / 0 °C 1.2: 0 - 20 °C 2.1: lithium aluminium tetrahydride / tetrahydrofuran / 48 h / 0 - 20 °C / Inert atmosphere 3.1: N,N,N,N,N,N-hexamethylphosphoric triamide; potassium hexamethylsilazane / tetrahydrofuran; toluene / 0.5 h / -78 - -22 °C / Inert atmosphere 3.2: -78 - 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | Stage #1: 2-(5-chloro-2-methyl-1H-indol-3-yl)acetic acid With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 0℃; Stage #2: morpholine In N,N-dimethyl-formamide at 0 - 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 6 h / 140 °C 2: L-Tartaric acid / ethanol / 3 h / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 6 h / 140 °C 2: L-Tartaric acid / ethanol / 3 h / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 6 h / 140 °C 2: L-Tartaric acid / ethanol / 3 h / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 6 h / 140 °C 2: L-Tartaric acid / ethanol / 3 h / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 6 h / 140 °C 2: L-Tartaric acid / ethanol / 3 h / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 6 h / 140 °C 2: L-Tartaric acid / ethanol / 3 h / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 6 h / 140 °C 2: L-Tartaric acid / ethanol / 3 h / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 6 h / 140 °C 2: L-Tartaric acid / ethanol / 3 h / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 6 h / 140 °C 2: L-Tartaric acid / ethanol / 3 h / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 6 h / 140 °C 2: L-Tartaric acid / ethanol / 3 h / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 6 h / 140 °C 2: L-Tartaric acid / ethanol / 3 h / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | at 140℃; for 6h; | 3.1.2. General procedure for the synthesis of 4-amino-5-mercapto-3-[(5-chloro-2-methyl-1H-indol-3-yl)methyl]1,2,4-triazole (2) 4-Amino-5-mercapto-3-[(5-chloro-2-methyl-1H-indol-3-yl)methyl]1,2,4-triazole 2 was synthesized by the fusion reactionof 5-chloro-2-methylindole-3-acetic acid 1 (50 mmol)and thiocarbohydrazide (50 mmol) in oil bath at 140°C for 6hours. The solid formed was cooled down to room temperaturebefore washed with a saturated sodium bicarbonate solution.The crude triazole was then recrystallized by using hotethanol. Yield is 83% [3, 25]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With oxone||potassium monopersulfate triple salt; sodium hydrogencarbonate In water; acetone at 20℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
49% | With glucose-6-phosphate; 6-phosphate dehydrogenase; oxygen; Fre protein of Escherichia coli; TsrE protein of Escherichia coli; nicotinamide adenine dinucleotide; flavin adenine dinucleotide In aq. buffer at 20℃; for 0.5h; Enzymatic reaction; enantioselective reaction; |
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