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CAS No. : | 1161730-21-7 | MDL No. : | MFCD20482768 |
Formula : | C8H6INS2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | BNVCQPDDDUOBRT-UHFFFAOYSA-N |
M.W : | 307.17 | Pubchem ID : | 66905885 |
Synonyms : |
|
Num. heavy atoms : | 12 |
Num. arom. heavy atoms : | 9 |
Fraction Csp3 : | 0.12 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 1.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 64.06 |
TPSA : | 66.43 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | Yes |
CYP2C9 inhibitor : | Yes |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.48 cm/s |
Log Po/w (iLOGP) : | 2.81 |
Log Po/w (XLOGP3) : | 3.8 |
Log Po/w (WLOGP) : | 3.62 |
Log Po/w (MLOGP) : | 2.99 |
Log Po/w (SILICOS-IT) : | 4.63 |
Consensus Log Po/w : | 3.57 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -4.63 |
Solubility : | 0.00724 mg/ml ; 0.0000236 mol/l |
Class : | Moderately soluble |
Log S (Ali) : | -4.89 |
Solubility : | 0.00396 mg/ml ; 0.0000129 mol/l |
Class : | Moderately soluble |
Log S (SILICOS-IT) : | -4.4 |
Solubility : | 0.0121 mg/ml ; 0.0000395 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.48 |
Signal Word: | Warning | Class: | |
Precautionary Statements: | P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313 | UN#: | |
Hazard Statements: | H315-H319 | 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 |
---|---|---|
76% | With potassium carbonate In tetrahydrofuran at 20℃; | 117.2 Step 2: To a stirred mixture of 6-iodobenzo[d]thiazole-2-thiol (0.5 g, 1.7 mmmol) and potassium carbonate(0.23 g, 1.7 mmol) in THF (10 mL) was added methyl iodide (0.12 mL, 1.1 mmol). After stirring at rt overnight, the mixturewas concentrated under reduced pressure to give a solid. The solid was partitioned between saturated aq sodiumcarbonate and DCM. The organic layer was dried over Na2SO4 and filtered, and concentrated under reduced pressureto give 6-iodo-2-(methylthio)benzo[d]thiazole as a off-white solid (0.4 g, 76%). 1H NMR (300 MHz, CDCl3) δ 8.07 (d, J= 1.2 Hz, 1H), 7.69 (dd, J = 1.8, 8.4 Hz, 1H), 7.58 (d, J = 8.4 Hz, 1H), 2.78 (s, 3H). LCMS (ESI) m/z 308 (M+H)+. |
With potassium carbonate In tetrahydrofuran at 20 - 30℃; | 6.6b 6-iodo-2-(methylthio)benzo[d]thiazole To a stirred, room temperature mixture of 6-iodobenzo[d]thiazole-2-thiol (Reference Example 6a, 1.5 g, 5.1 mmol) and potassium carbonate (0.707 g, 5.1 mmol) in tetrahydrofuran (30 mL) was added methyl iodide (0.35 mL, 5.6 mmol). The reaction mixture was stirred at room temperature overnight, then volatiles were removed under reduced pressure to give a solid. The solid was partitioned between saturated aqueous sodium carbonate and chloroform. The chloroform layer was dried (MgSO4) and filtered. The filtrate was concentrated under reduced pressure to provide 6-iodo-2-(methylthio)benzo[d]thiazole. 1H NMR (300 MHz, CDCl3) δ ppm 2.78 (s, 3H), 7.58 (d, J=9 Hz, 1H), 7.69 (dd, J=2, 9 Hz, 1H), 8.07 (d, J=2 Hz, 1H); MS (DCI/NH3) m/z 308 (M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium permanganate; water; acetic acid at 20 - 30℃; for 68h; | 6.6c 6-iodo-2-(methylsulfonyl)benzo[d]thiazole To a stirred, room temperature solution of 6-iodo-2-(methylthio)benzo[d]thiazole (Reference Example 6b, 1.22 g, 4.0 mmol) in acetic acid (100 mL) was added dropwise a solution of potassium permanganate (0.190 g, 1.2 mmol) in water (60 mL). The reaction mixture was stirred at room temperature for 68 hours, then quenched with aqueous sodium sulfite. The resulting mixture was vigorously stirred at room temperature overnight. The resulting precipitate was collected by filtration and rinsed with water. The solid was dissolved in ethyl acetate, dried (MgSO4), and filtered. The filtrate was concentrated under reduced pressure to provide 6-iodo-2-(methylsulfonyl)benzo[d]thiazole. 1H NMR (300 MHz, CDCl3) δ ppm 3.41 (s, 3H), 7.93 (d, J=1 Hz, 2H), 8.38 (t, J=1 Hz, 1H); MS (DCI/NH3) m/z 340 (M+H)-, 357 (M+NH4)-. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: palladium diacetate; tris-(o-tolyl)phosphine; sodium hydrogencarbonate / N,N-dimethyl-formamide / 4 h / 100 °C / Inert atmosphere 2: <i>L</i>-proline; N-chloro-succinimide / dichloromethane / 0 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: palladium diacetate; tris-(o-tolyl)phosphine; sodium hydrogencarbonate / N,N-dimethyl-formamide / 4 h / 100 °C / Inert atmosphere 2: <i>L</i>-proline; N-chloro-succinimide / dichloromethane / 0 - 20 °C 3: butan-1-ol / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: palladium diacetate; tris-(o-tolyl)phosphine; sodium hydrogencarbonate / N,N-dimethyl-formamide / 4 h / 100 °C / Inert atmosphere 2: <i>L</i>-proline; N-chloro-succinimide / dichloromethane / 0 - 20 °C 3: butan-1-ol / Reflux 4: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: palladium diacetate; tris-(o-tolyl)phosphine; sodium hydrogencarbonate / N,N-dimethyl-formamide / 4 h / 100 °C / Inert atmosphere 2: <i>L</i>-proline; N-chloro-succinimide / dichloromethane / 0 - 20 °C 3: butan-1-ol / Reflux 4: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / 0 °C 5: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 48 h / 140 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: palladium diacetate; tris-(o-tolyl)phosphine; sodium hydrogencarbonate / N,N-dimethyl-formamide / 4 h / 100 °C / Inert atmosphere 2: <i>L</i>-proline; N-chloro-succinimide / dichloromethane / 0 - 20 °C 3: butan-1-ol / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: palladium diacetate; tris-(o-tolyl)phosphine; sodium hydrogencarbonate / N,N-dimethyl-formamide / 4 h / 100 °C / Inert atmosphere 2: <i>L</i>-proline; N-chloro-succinimide / dichloromethane / 0 - 20 °C 3: butan-1-ol / Reflux 4: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: palladium diacetate; tris-(o-tolyl)phosphine; sodium hydrogencarbonate / N,N-dimethyl-formamide / 4 h / 100 °C / Inert atmosphere 2: <i>L</i>-proline; N-chloro-succinimide / dichloromethane / 0 - 20 °C 3: butan-1-ol / Reflux 4: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / 0 °C 5: N-ethyl-N,N-diisopropylamine / 1-methyl-pyrrolidin-2-one / 48 h / 140 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: palladium diacetate; tris-(o-tolyl)phosphine; sodium hydrogencarbonate / N,N-dimethyl-formamide / 4 h / 100 °C / Inert atmosphere 2: <i>L</i>-proline; N-chloro-succinimide / dichloromethane / 0 - 20 °C 3: butan-1-ol / 15 h / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: palladium diacetate; tris-(o-tolyl)phosphine; sodium hydrogencarbonate / N,N-dimethyl-formamide / 4 h / 100 °C / Inert atmosphere 2: <i>L</i>-proline; N-chloro-succinimide / dichloromethane / 0 - 20 °C 3: butan-1-ol / 15 h / Reflux 4: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: palladium diacetate; tris-(o-tolyl)phosphine; sodium hydrogencarbonate / N,N-dimethyl-formamide / 4 h / 100 °C / Inert atmosphere 2: <i>L</i>-proline; N-chloro-succinimide / dichloromethane / 0 - 20 °C 3: butan-1-ol / 15 h / Reflux 4: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / 0 °C 5: N-ethyl-N,N-diisopropylamine / 1-methyl-pyrrolidin-2-one / 48 h / 140 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: palladium diacetate; tris-(o-tolyl)phosphine; sodium hydrogencarbonate / N,N-dimethyl-formamide / 4 h / 100 °C / Inert atmosphere 2: <i>L</i>-proline; N-chloro-succinimide / dichloromethane / 0 - 20 °C 3: butan-1-ol / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: palladium diacetate; tris-(o-tolyl)phosphine; sodium hydrogencarbonate / N,N-dimethyl-formamide / 4 h / 100 °C / Inert atmosphere 2: <i>L</i>-proline; N-chloro-succinimide / dichloromethane / 0 - 20 °C 3: butan-1-ol / Reflux 4: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: palladium diacetate; tris-(o-tolyl)phosphine; sodium hydrogencarbonate / N,N-dimethyl-formamide / 4 h / 100 °C / Inert atmosphere 2: <i>L</i>-proline; N-chloro-succinimide / dichloromethane / 0 - 20 °C 3: butan-1-ol / Reflux 4: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / 0 °C 5: N-ethyl-N,N-diisopropylamine / 1-methyl-pyrrolidin-2-one / 24 h / 140 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: palladium diacetate; tris-(o-tolyl)phosphine; sodium hydrogencarbonate / N,N-dimethyl-formamide / 4 h / 100 °C / Inert atmosphere 2: <i>L</i>-proline; N-chloro-succinimide / dichloromethane / 0 - 20 °C 3: butan-1-ol / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: palladium diacetate; tris-(o-tolyl)phosphine; sodium hydrogencarbonate / N,N-dimethyl-formamide / 4 h / 100 °C / Inert atmosphere 2: <i>L</i>-proline; N-chloro-succinimide / dichloromethane / 0 - 20 °C 3: butan-1-ol / Reflux 4: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: palladium diacetate; tris-(o-tolyl)phosphine; sodium hydrogencarbonate / N,N-dimethyl-formamide / 4 h / 100 °C / Inert atmosphere 2: <i>L</i>-proline; N-chloro-succinimide / dichloromethane / 0 - 20 °C 3: butan-1-ol / Reflux 4: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / 0 °C 5: N-ethyl-N,N-diisopropylamine / 1-methyl-pyrrolidin-2-one / 24 h / 130 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: palladium diacetate; tris-(o-tolyl)phosphine; sodium hydrogencarbonate / N,N-dimethyl-formamide / 4 h / 100 °C / Inert atmosphere 2: <i>L</i>-proline; N-chloro-succinimide / dichloromethane / 0 - 20 °C 3: butan-1-ol / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: palladium diacetate; tris-(o-tolyl)phosphine; sodium hydrogencarbonate / N,N-dimethyl-formamide / 4 h / 100 °C / Inert atmosphere 2: <i>L</i>-proline; N-chloro-succinimide / dichloromethane / 0 - 20 °C 3: butan-1-ol / Reflux 4: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: palladium diacetate; tris-(o-tolyl)phosphine; sodium hydrogencarbonate / N,N-dimethyl-formamide / 4 h / 100 °C / Inert atmosphere 2: <i>L</i>-proline; N-chloro-succinimide / dichloromethane / 0 - 20 °C 3: butan-1-ol / Reflux 4: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / 0 °C 5: N-ethyl-N,N-diisopropylamine / 1-methyl-pyrrolidin-2-one / 48 h / 140 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: palladium diacetate; tris-(o-tolyl)phosphine; sodium hydrogencarbonate / N,N-dimethyl-formamide / 4 h / 100 °C / Inert atmosphere 2: <i>L</i>-proline; N-chloro-succinimide / dichloromethane / 0 - 20 °C 3: butan-1-ol / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: palladium diacetate; tris-(o-tolyl)phosphine; sodium hydrogencarbonate / N,N-dimethyl-formamide / 4 h / 100 °C / Inert atmosphere 2: <i>L</i>-proline; N-chloro-succinimide / dichloromethane / 0 - 20 °C 3: butan-1-ol / Reflux 4: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: palladium diacetate; tris-(o-tolyl)phosphine; sodium hydrogencarbonate / N,N-dimethyl-formamide / 4 h / 100 °C / Inert atmosphere 2: <i>L</i>-proline; N-chloro-succinimide / dichloromethane / 0 - 20 °C 3: butan-1-ol / Reflux 4: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / 0 °C 5: N-ethyl-N,N-diisopropylamine / 1-methyl-pyrrolidin-2-one / 135 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
52% | With palladium diacetate; sodium hydrogencarbonate; tris-(o-tolyl)phosphine In N,N-dimethyl-formamide at 100℃; for 4h; Inert atmosphere; | 117.3 Step 3: A mixture of 6-iodo-2-(methylthio)benzo[d]thiazole (5.0 g, 16.3 mmol), allyl alcohol (2.2 mL, 32.6 mmol),Pd(OAc)2 (0.36 g, 1.63 mmol), tris(o-tolyl) phosphine (1.0 g, 3.3 mmol) and NaHCO3 (2.8 g, 32.6 mmol) in DMF (75 mL)was stirred at 100 °C under nitrogen atmosphere for 4 h. Then the mixture was cooled to rt and water (300 mL) wasadded. The mixture was extracted with EtOAc (200 mL3 3). The combined organic layers were washed with brine, driedover Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatographyeluting with 10: 1 to 5: 1 petroleum ether/EtOAc to afford 3-(2-(methylthio)benzo[d]thiazol-6-yl)propanal as a dark yellowoil (2.0 g, 52%). 1H NMR (300 MHz, CDCl3) δ 9.83 (t, J = 1.2 Hz, 1H), 7.78 (d, J = 8.4 Hz, 1H), 7.58 (d, J = 1.2 Hz, 1H),7.23 (dd, J = 1.8, 8.4 Hz, 1H), 3.05 (t, J = 7.5 Hz, 2H), 2.85 (t, J = 7.5 Hz, 2H), 2.78 (s, 3H). LCMS (ESI) m/z 238 (M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: N,N-dimethyl-formamide / 5 h / 95 °C 2: potassium carbonate / tetrahydrofuran / 20 °C |