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CAS No. : | 17402-91-4 | MDL No. : | MFCD18451789 |
Formula : | C8H7NS | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | XATYIBVSSKQMDX-UHFFFAOYSA-N |
M.W : | 149.21 | Pubchem ID : | 14765536 |
Synonyms : |
|
Num. heavy atoms : | 10 |
Num. arom. heavy atoms : | 9 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 0.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 46.23 |
TPSA : | 54.26 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) : | -5.61 cm/s |
Log Po/w (iLOGP) : | 1.7 |
Log Po/w (XLOGP3) : | 2.26 |
Log Po/w (WLOGP) : | 2.49 |
Log Po/w (MLOGP) : | 1.84 |
Log Po/w (SILICOS-IT) : | 2.97 |
Consensus Log Po/w : | 2.25 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.85 |
Solubility : | 0.208 mg/ml ; 0.0014 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.04 |
Solubility : | 0.137 mg/ml ; 0.000921 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -2.96 |
Solubility : | 0.162 mg/ml ; 0.00109 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.71 |
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 |
---|---|---|
1: 39% 2: 41% | at 500℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
34% | With bromine In dichloromethane at -78℃; for 1.5h; | P64.1 Step 1 : 4-Bromobenzo[b1thiophen-7-amine (P64a) Step 1 : 4-Bromobenzo[b1thiophen-7-amine (P64a) To a solution of benzo[b]thiophen-7-amine (4.65 g, 30 mmol) in DCM (100 mL) was added a solution of Br2 (4.99 g, 0.03 mL) in DCM (120 mL) at -78°C and the solution was stirred for 1.5 h at -78°C, quenched with water and extracted with DCM (3x). The combined organic layers were washed with water and brine, dried over Na2S04, filtered, concentrated and purified by CC (PE/EA = 30/1 ) to give of compound P64a (2.38 g, 34%) as a colorless solid. 'H-NMR (400 MHz, CD3OD) δ: 6.62 (d, J = 8.0 Hz, 1 H), 7.30 (d, J = 8.4 Hz, 1 H), 7.40 (d, J = 5.2 Hz, 1 H), 7.62 (d, J = 6.0 Hz, 1 H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: bromine / dichloromethane / 1.5 h / -78 °C 2.1: hydrogenchloride; acetic acid; sodium nitrite / water / 1 h / -5 - 0 °C 2.2: 2 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: bromine / dichloromethane / 1.5 h / -78 °C 2.1: hydrogenchloride; acetic acid; sodium nitrite / water / 1 h / -5 - 0 °C 2.2: 2 h / 20 °C 3.1: pyridine / dichloromethane / 1 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: hydrogenchloride / dimethyl sulfoxide; water / 24 h / 150 °C 2: palladium on activated charcoal; hydrogen / ethyl acetate / 4 h / 20 °C | ||
Multi-step reaction with 3 steps 1: sodium hydroxide; methanol / 2 h 2: copper(I) oxide / N,N-dimethyl-formamide / 2 h / 120 °C 3: palladium on activated charcoal; hydrogen / ethyl acetate / 4 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: potassium carbonate / N,N-dimethyl-formamide / 6 h / 10 °C / Inert atmosphere; Cooling with ice 2: hydrogenchloride / dimethyl sulfoxide; water / 24 h / 150 °C 3: palladium on activated charcoal; hydrogen / ethyl acetate / 4 h / 20 °C | ||
Multi-step reaction with 4 steps 1: potassium carbonate / N,N-dimethyl-formamide / 6 h / 10 °C / Inert atmosphere; Cooling with ice 2: sodium hydroxide; methanol / 2 h 3: copper(I) oxide / N,N-dimethyl-formamide / 2 h / 120 °C 4: palladium on activated charcoal; hydrogen / ethyl acetate / 4 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: copper(I) oxide / N,N-dimethyl-formamide / 2 h / 120 °C 2: palladium on activated charcoal; hydrogen / ethyl acetate / 4 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1.1 g | With palladium on activated charcoal; hydrogen In ethyl acetate at 20℃; for 4h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: potassium carbonate / isopropyl alcohol / 14 h / Reflux 2: hydrogenchloride / ethanol / 2 h / 55 °C / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: potassium carbonate / isopropyl alcohol / 14 h / Reflux 2: hydrogenchloride / ethanol / 2 h / 55 °C / Reflux 3: triethylamine / dichloromethane / 2 h / 10 °C / Cooling with ice | ||
Multi-step reaction with 4 steps 1.1: tetrahydrofuran / 12 h 2.1: triethylamine / dichloromethane / 10 °C / Cooling with ice 2.2: 3 h 3.1: potassium carbonate / acetonitrile / 16 h / Reflux 4.1: 2-chloropyridine; trifluoroacetyl triflate / dichloromethane / 1.5 h / 20 °C 4.2: 24 h / 20 °C | ||
Multi-step reaction with 4 steps 1.1: tetrahydrofuran / 12 h 2.1: triethylamine / dichloromethane / 10 °C / Cooling with ice 2.2: 3 h 3.1: potassium carbonate / acetonitrile / 16 h / Reflux 4.1: 2-chloropyridine; trifluoroacetyl triflate / dichloromethane / 1.5 h / 20 °C 4.2: 27 h / 20 °C / 150.01 - 375.04 Torr |
Multi-step reaction with 6 steps 1.1: tetrahydrofuran / 12 h 2.1: triethylamine / dichloromethane / 10 °C / Cooling with ice 2.2: 3 h 3.1: potassium carbonate / acetonitrile / 12 h / Reflux 4.1: palladium on activated charcoal; hydrogen / tetrahydrofuran / 8 h / 45 °C 5.1: potassium carbonate / acetonitrile 5.2: 8 h / 75 °C 6.1: 2-chloropyridine; trifluoroacetyl triflate / dichloromethane / 1.5 h / 20 °C 6.2: 24 h / 20 °C | ||
Multi-step reaction with 6 steps 1.1: tetrahydrofuran / 12 h 2.1: triethylamine / dichloromethane / 10 °C / Cooling with ice 2.2: 3 h 3.1: potassium carbonate / acetonitrile / 12 h / Reflux 4.1: palladium on activated charcoal; hydrogen / tetrahydrofuran / 8 h / 45 °C 5.1: potassium carbonate / acetonitrile 5.2: 8 h / 75 °C 6.1: 2-chloropyridine; trifluoroacetyl triflate / dichloromethane / 1.5 h / 20 °C 6.2: 27 h / 20 °C / 150.01 - 375.04 Torr | ||
Multi-step reaction with 6 steps 1.1: tetrahydrofuran / 12 h 2.1: triethylamine / dichloromethane / 10 °C / Cooling with ice 2.2: 3 h 3.1: potassium carbonate / acetonitrile / 12 h / Reflux 4.1: palladium on activated charcoal; hydrogen / tetrahydrofuran / 8 h / 45 °C 5.1: triethylamine / dichloromethane / 0.17 h / 25 °C 5.2: 24 h / 25 °C 6.1: 2-chloropyridine; trifluoroacetyl triflate / dichloromethane / 1.5 h / 20 °C 6.2: 24 h / 20 °C | ||
Multi-step reaction with 6 steps 1.1: tetrahydrofuran / 12 h 2.1: triethylamine / dichloromethane / 10 °C / Cooling with ice 2.2: 3 h 3.1: potassium carbonate / acetonitrile / 12 h / Reflux 4.1: palladium on activated charcoal; hydrogen / tetrahydrofuran / 8 h / 45 °C 5.1: triethylamine / dichloromethane / 0.17 h / 25 °C 5.2: 24 h / 25 °C 6.1: 2-chloropyridine; trifluoroacetyl triflate / dichloromethane / 1.5 h / 20 °C 6.2: 27 h / 20 °C / 150.01 - 375.04 Torr |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate In isopropyl alcohol for 14h; Reflux; | 6 Example 6 7-aminobenzothiophene (1.49g, 0.01mol), bis (2-chloroethyl) amine hydrochloride (1.77g, 0.01mol, 1eq), potassium carbonate (2.76g) prepared by the preparation method of Example 5 , 0.02mol, 2eq), isopropanol (40ml), mixed and stirred, heated to reflux for 14 hours. The solvent was spin-dried, the residue was stirred with water and ethyl acetate, and the layers were separated. The aqueous phase was extracted with ethyl acetate. The organic phases were combined, washed with saturated brine, dried over anhydrous sodium sulfate, filtered with suction, and spin-dried to obtain a crude yellow oil. 2.8g; Dissolve the above crude product (2.8g) in 20ml of ethanol, add 30% hydrogen chloride ethanol solution (3ml) and stir, a white solid precipitates. After stirring for 1h, filter with suction. The filter cake is rinsed with ice ethanol and dried to obtain 7-piper Azinylbenzothiophene hydrochloride, white solid 2.11g, yield 83%. The total yield from 3-nitrosalicylic aldehyde (Compound 2) to 7-piperazinylbenzothiophene hydrochloride was 74.7%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With potassium carbonate In isopropyl alcohol for 14h; Reflux; | 7 Example 7 7-aminobenzothiophene (1.49g, 0.01mol), N-Boc-bis (2-chloroethyl) amine (2.41g, 0.01mol, 1eq), potassium carbonate (2.76g, 0.02mol, 2eq), iso Propyl alcohol (40ml), mixed and stirred, heated to reflux for 14 hours. The solvent was spin-dried, the residue was stirred with water and ethyl acetate, and the liquid was separated. The aqueous phase was extracted with ethyl acetate. The combined organic phases were washed with saturated brine, dried over anhydrous sodium sulfate, filtered with suction, and spin-dried to obtain a crude yellow oil 3.7g. Column chromatography purification, eluent petroleum ether: ethyl acetate = 30: 1 ~ 10: 1, to obtain a white solid 2.4g (compound 9-2), 75% yield. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
3 g | With potassium carbonate In isopropyl alcohol for 14h; Reflux; | 9 Example 9 Compound 8-3 prepared in Example 8 (4.86g, 0.01mol), 7-aminobenzothiophene (Compound 7) (1.49g, 0.01mol, 1eq), potassium carbonate (2.76g, 0.02mol, 2eq) Mix with isopropanol (50ml), and heat to reflux for 14 hours. The solvent was spin-dried, the residue was stirred with water and ethyl acetate, and the liquid was separated. The aqueous phase was extracted with ethyl acetate. The combined organic phases were washed with saturated brine, dried over anhydrous sodium sulfate, filtered with suction, and spin-dried to obtain a crude yellow oil. 6g. Column chromatography purification, eluent petroleum ether: ethyl acetate = 1: 1 ~ 0: 1, to obtain compound 9-1, off-white solid 3g. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
0.84 g | With potassium carbonate In <i>tert</i>-butyl alcohol at 100℃; for 14h; | 11 Example 11 Compound 8-4 (1.83g, 0.004mol) prepared in Example 10, 7-aminobenzothiophene (Compound 7) (0.6g, 0.004mol), potassium carbonate (1.1g, 0.008mol, 2eq), tertiary Butanol (30 ml) was mixed and stirred, and the reaction was heated at 100 ° C for 14 hours. The solvent was spin-dried, the residue was stirred with water and ethyl acetate, and the liquid was separated. The aqueous phase was extracted with ethyl acetate. The combined organic phases were washed with saturated brine, dried over anhydrous sodium sulfate, filtered with suction, and spin-dried to obtain a crude yellow oil. 2g. Column chromatography purification, eluent dichloromethane: methanol = 50: 1 ~ 30: 1, to obtain an off-white solid 1.2g, recrystallized from ethyl acetate to obtain a white solid 0.84g (compound I). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: triethylamine / dichloromethane / 4 h / 10 °C / Cooling with ice 2: potassium carbonate / N,N-dimethyl-formamide / 6 h / 10 °C / Inert atmosphere; Cooling with ice 3: hydrogenchloride / dimethyl sulfoxide; water / 24 h / 150 °C 4: palladium on activated charcoal; hydrogen / ethyl acetate / 4 h / 20 °C | ||
Multi-step reaction with 5 steps 1: triethylamine / dichloromethane / 4 h / 10 °C / Cooling with ice 2: potassium carbonate / N,N-dimethyl-formamide / 6 h / 10 °C / Inert atmosphere; Cooling with ice 3: sodium hydroxide; methanol / 2 h 4: copper(I) oxide / N,N-dimethyl-formamide / 2 h / 120 °C 5: palladium on activated charcoal; hydrogen / ethyl acetate / 4 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: potassium carbonate / N,N-dimethyl-formamide / 6 h / 10 °C / Inert atmosphere; Cooling with ice 2: hydrogenchloride / dimethyl sulfoxide; water / 24 h / 150 °C 3: palladium on activated charcoal; hydrogen / ethyl acetate / 4 h / 20 °C | ||
Multi-step reaction with 4 steps 1: potassium carbonate / N,N-dimethyl-formamide / 6 h / 10 °C / Inert atmosphere; Cooling with ice 2: sodium hydroxide; methanol / 2 h 3: copper(I) oxide / N,N-dimethyl-formamide / 2 h / 120 °C 4: palladium on activated charcoal; hydrogen / ethyl acetate / 4 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: tetrahydrofuran / 12 h 2.1: triethylamine / dichloromethane / 10 °C / Cooling with ice 2.2: 3 h 3.1: potassium carbonate / acetonitrile / 16 h / Reflux | ||
Multi-step reaction with 5 steps 1.1: tetrahydrofuran / 12 h 2.1: triethylamine / dichloromethane / 10 °C / Cooling with ice 2.2: 3 h 3.1: potassium carbonate / acetonitrile / 12 h / Reflux 4.1: palladium on activated charcoal; hydrogen / tetrahydrofuran / 8 h / 45 °C 5.1: potassium carbonate / acetonitrile 5.2: 8 h / 75 °C | ||
Multi-step reaction with 5 steps 1.1: tetrahydrofuran / 12 h 2.1: triethylamine / dichloromethane / 10 °C / Cooling with ice 2.2: 3 h 3.1: potassium carbonate / acetonitrile / 12 h / Reflux 4.1: palladium on activated charcoal; hydrogen / tetrahydrofuran / 8 h / 45 °C 5.1: triethylamine / dichloromethane / 0.17 h / 25 °C 5.2: 24 h / 25 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: tetrahydrofuran / 12 h 2.1: triethylamine / dichloromethane / 10 °C / Cooling with ice 2.2: 3 h 3.1: potassium carbonate / acetonitrile / 12 h / Reflux | ||
Multi-step reaction with 3 steps 1.1: tetrahydrofuran / 12 h 2.1: triethylamine / dichloromethane / Cooling with ice 2.2: 3 h / 10 °C / Heating 3.1: potassium carbonate / acetonitrile / 12 h / Reflux | ||
Multi-step reaction with 3 steps 1: tetrahydrofuran / 12 h 2: N,N-dimethyl-formamide; oxalyl dichloride / dichloromethane / 3 h / 10 °C / Heating 3: potassium carbonate / acetonitrile / 12 h / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: tetrahydrofuran / 12 h 2.1: triethylamine / dichloromethane / 10 °C / Cooling with ice 2.2: 3 h 3.1: potassium carbonate / acetonitrile / 12 h / Reflux 4.1: palladium on activated charcoal; hydrogen / tetrahydrofuran / 8 h / 45 °C | ||
Multi-step reaction with 4 steps 1.1: tetrahydrofuran / 12 h 2.1: triethylamine / dichloromethane / Cooling with ice 2.2: 3 h / 10 °C / Heating 3.1: potassium carbonate / acetonitrile / 12 h / Reflux 4.1: palladium on activated charcoal; hydrogen / tetrahydrofuran / 8 h / 45 °C | ||
Multi-step reaction with 4 steps 1: tetrahydrofuran / 12 h 2: N,N-dimethyl-formamide; oxalyl dichloride / dichloromethane / 3 h / 10 °C / Heating 3: potassium carbonate / acetonitrile / 12 h / Reflux 4: palladium on activated charcoal; hydrogen / tetrahydrofuran / 8 h / 45 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: tetrahydrofuran / 12 h 2.1: triethylamine / dichloromethane / 10 °C / Cooling with ice 2.2: 3 h | ||
Multi-step reaction with 2 steps 1.1: tetrahydrofuran / 12 h 2.1: triethylamine / dichloromethane / Cooling with ice 2.2: 3 h / 10 °C / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In tetrahydrofuran for 12h; | 1 7-aminobenzothiophene (1.49g, 0.01mol),Ethylene oxide (4ml) and tetrahydrofuran (40ml) were mixed and stirred for 12h,Sampling to test the reaction is complete, spin the solvent,2.2g of compound II yellow oil was obtained, and the crude product was directly used in the next step; | |
In tetrahydrofuran for 12h; | 1; 4 Example 1 7-Aminobenzothiophene (1.49g, 0.01mol), ethylene oxide (4ml) and tetrahydrofuran (40ml) were mixed and stirred for 12h. The reaction was sampled and detected to be complete, and the solvent was spin-dried to obtain 2.2g of compound 2 as a yellow oil The crude product goes directly to the next step. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: tetrahydrofuran / 12 h 2.1: triethylamine / dichloromethane / Cooling with ice 2.2: 3 h / 10 °C / Heating 3.1: potassium carbonate / acetonitrile / 12 h / Reflux 4.1: palladium on activated charcoal; hydrogen / ethanol / 8 h / 45 °C 4.2: 0.5 h | ||
Multi-step reaction with 4 steps 1.1: tetrahydrofuran / 12 h 2.1: N,N-dimethyl-formamide; oxalyl dichloride / dichloromethane / 3 h / 10 °C / Heating 3.1: potassium carbonate / acetonitrile / 12 h / Reflux 4.1: palladium on activated charcoal; hydrogen / ethanol / 8 h / 45 °C 4.2: 0.5 h | ||
Multi-step reaction with 5 steps 1.1: tetrahydrofuran / 12 h 2.1: triethylamine / dichloromethane / Cooling with ice 2.2: 3 h / 10 °C / Heating 3.1: potassium carbonate / acetonitrile / 12 h / Reflux 4.1: palladium on activated charcoal; hydrogen / tetrahydrofuran / 8 h / 45 °C 5.1: hydrogenchloride / ethanol / 4 h / 55 °C |
Multi-step reaction with 5 steps 1: tetrahydrofuran / 12 h 2: N,N-dimethyl-formamide; oxalyl dichloride / dichloromethane / 3 h / 10 °C / Heating 3: potassium carbonate / acetonitrile / 12 h / Reflux 4: palladium on activated charcoal; hydrogen / tetrahydrofuran / 8 h / 45 °C 5: hydrogenchloride / ethanol / 4 h / 55 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: tetrahydrofuran / 12 h 2.1: triethylamine / dichloromethane / Cooling with ice 2.2: 3 h / 10 °C / Heating 3.1: potassium carbonate / acetonitrile / 12 h / Reflux 4.1: palladium on activated charcoal; hydrogen / tetrahydrofuran / 8 h / 45 °C | ||
Multi-step reaction with 4 steps 1: tetrahydrofuran / 12 h 2: N,N-dimethyl-formamide; oxalyl dichloride / dichloromethane / 3 h / 10 °C / Heating 3: potassium carbonate / acetonitrile / 12 h / Reflux 4: palladium on activated charcoal; hydrogen / tetrahydrofuran / 8 h / 45 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: tetrahydrofuran / 12 h 2: N,N-dimethyl-formamide; oxalyl dichloride / dichloromethane / 3 h / 10 °C / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: tetrahydrofuran / 12 h 2: phosphorus tribromide / dichloromethane / 3 h / 10 °C / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: tetrahydrofuran / 12 h 2.1: triethylamine / dichloromethane / Cooling with ice 2.2: 3 h / 10 °C / Heating 3.1: potassium carbonate / acetonitrile / 16 h / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: tetrahydrofuran / 12 h 2.1: triethylamine / dichloromethane / Cooling with ice 2.2: 3 h / 10 °C / Heating 3.1: potassium carbonate / acetonitrile / 16 h / Reflux | ||
Multi-step reaction with 4 steps 1.1: tetrahydrofuran / 12 h 2.1: triethylamine / dichloromethane / Cooling with ice 2.2: 3 h / 10 °C / Heating 3.1: potassium carbonate / acetonitrile / 16 h / Reflux 4.1: 2-chloropyridine; trifluoromethylsulfonic anhydride / dichloromethane / 1.5 h / 20 °C 4.2: 24 h / 20 °C |