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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
Phenothiazine, a dopamine2 (D2) receptor antagonist, could reduce the expression of dopamine in the brain.
Synonyms: Thiodiphenylamine; ENT 38; NSC-2037 NSC2037
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Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
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CAS No. : | 92-84-2 |
Formula : | C12H9NS |
M.W : | 199.27 |
SMILES Code : | C12=CC=CC=C1NC3=C(C=CC=C3)S2 |
Synonyms : |
Thiodiphenylamine; ENT 38; NSC-2037 NSC2037
|
MDL No. : | MFCD00005015 |
InChI Key : | WJFKNYWRSNBZNX-UHFFFAOYSA-N |
Pubchem ID : | 7108 |
GHS Pictogram: |
![]() ![]() ![]() |
Signal Word: | Danger |
Hazard Statements: | H302-H315+H320-H370-H373-H317-H335-H410 |
Precautionary Statements: | P501-P273-P272-P260-P270-P271-P264-P280-P302+P352-P391-P337+P313-P305+P351+P338-P308+P311-P362+P364-P333+P313-P301+P312+P330-P304+P340+P312-P403+P233-P405 |
Class: | 9 |
UN#: | 3077 |
Packing Group: | Ⅲ |
* 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 |
---|---|---|
45% | With N-Bromosuccinimide In tetrahydrofuran at 0℃; for 16 h; Inert atmosphere | In a nitrogen-flushed 250 mL round-bottom flask with a magnetic stir bar and septum 10Hphenothiazine (7.97 g, 40.0 mmol) was dissolved in dry THF (60 mL) under nitrogen. The dark solution was deaerated by a constant stream of nitrogen through a syringe for 10 min and cooled to 0 °C (ice bath/water). N-Bromosuccinimide (7.12 g, 40.0 mmol) was slowly added to the reaction mixture under nitrogen, then stirred for 16 h and allowed to come to room tempetature. To this solution was added a saturated aqueous solution of sodium sulfite (150 mL) and the aqueous layer was extracted several times with dichloromethane. The combined organic layers were dried with anhydrous magnesium sulfate and filtered. Thesolvents were removed in vacuo and the residue was adsorbed onto celite®and purified by chromatography on silica gel (n-hexane/ethyl acetate 20:1) to give 4.95 g (45percent) of 3-bromo-10H-phenothiazine as a colorless solid, Rf (n-hexane/acetone 4:1) = 0.33. The 1H NMRspectrum was in agreement with the literature.1H NMR (CDCl3, 300 MHz): 5.89 (s, br, 1 H), 6.52 (m, 1 H), 6.61 (m, 1 H), 6.83-7.15 (m, 5 H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
EXAMPLE 4 Synthesis of Bis(trimethylsilyl)methylacrylate Bis(trimethylsilyl)chloromethane (Aldrich) 39 g, 0.2 mole), <strong>[7446-81-3]sodium acrylate</strong> (28 g, 0.3 mole), Adogen 464 (Aldrich) (6.96 g), and phenothiazine (0.10 grams) were placed in a round bottom flask equipped with a condenser, mechanical stirrer and a nitrogen inlet. The flask was charged with 100 ml of butyronitrile and heated to reflux while stirring. After 6 hours, the mixture was diluted with 150 ml hexanes and filtered to remove the solids. The solvents were removed under reduced pressure. Fractional distillation of the residue under reduced pressure gave 35.5 grams 975percent) of the desired product at 45-58° C. at 0.5 mm pressure. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
45% | With N-Bromosuccinimide; In tetrahydrofuran; at 0℃; for 16h;Inert atmosphere; | In a nitrogen-flushed 250 mL round-bottom flask with a magnetic stir bar and septum 10Hphenothiazine (7.97 g, 40.0 mmol) was dissolved in dry THF (60 mL) under nitrogen. The dark solution was deaerated by a constant stream of nitrogen through a syringe for 10 min and cooled to 0 C (ice bath/water). N-Bromosuccinimide (7.12 g, 40.0 mmol) was slowly added to the reaction mixture under nitrogen, then stirred for 16 h and allowed to come to room tempetature. To this solution was added a saturated aqueous solution of sodium sulfite (150 mL) and the aqueous layer was extracted several times with dichloromethane. The combined organic layers were dried with anhydrous magnesium sulfate and filtered. Thesolvents were removed in vacuo and the residue was adsorbed onto celiteand purified by chromatography on silica gel (n-hexane/ethyl acetate 20:1) to give 4.95 g (45%) of 3-bromo-10H-phenothiazine as a colorless solid, Rf (n-hexane/acetone 4:1) = 0.33. The 1H NMRspectrum was in agreement with the literature.1H NMR (CDCl3, 300 MHz): 5.89 (s, br, 1 H), 6.52 (m, 1 H), 6.61 (m, 1 H), 6.83-7.15 (m, 5 H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | 1.41 g of phenothiazine,240 mg of 70% oil dispersion of sodium hydride and.20 ml of tetrahydrofuran was added to a 50 ml single-neck round bottom flask,After refluxing under argon for 30 minutes, 0.75 g of 4,7-dichloro-1,10 phenanthroline were added., Then refluxed at 60 C for 24 hours,After cooling to room temperature, saturated saline was quenched,Dichloromethane extraction,The organic phase was dried over anhydrous sodium sulfate,Filtered, and dried.A methanol: dichloromethane volume ratio of 1:30 to obtain the product 1.38 grams. Light yellow solid, yield 80% |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86.98% | Phenothiazine 16.20mmol 48.49mmol added sodium t-butoxide and 33ml toluene was added after the reaction flask under a nitrogen blanket. After stirring 10min, tris (dibenzylideneacetone) dipalladium 0.203mmol, tri-tert-butylphosphine 1.295 mmol,<strong>[62162-97-4]2-bromophenanthrene</strong> 24.3mmol, ventilation three times, 110 reflux overnight. After the reaction, dichloromethane 100ml extraction, evaporation of organic phase after a small amount of dichloromethane dissolved with petroleum ether precipitation products, the product of petroleum ether 100ml wash 3 times, ethanol 100ml, washed 2 times to get light yellow Product 14.09 mmol, yield 86.98percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
58% | With copper; potassium carbonate; In 1-methyl-pyrrolidin-2-one; for 48h;Inert atmosphere; Reflux; | Intermediate a (3.61 g, 9 mmol) obtained in Intermediate Preparation Example and phenothiazine (4.48 g, 22.5 mmol) were dissolved in 50 mL of NMP under nitrogen atmosphere and then catalyst copper (1.72 g, 27 mmol) Acid-binding agent and potassium carbonate (4.97g, 36mmol). The system was heated to reflux for 48 hours, naturally cooled to 20 ~ 25 ° C after adding 100mL water quenched reaction, the product was filtered to give the crude product.Silica gel column chromatography, eluent methylene chloride: n-hexane = 1: 7 (V / V), to give a white powder, the resulting powder using chemical vapor deposition system further sublimation purification, sublimation temperature of 250 ° C, to give compound C15 , Yield 58percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With tri-tert-butyl phosphine; palladium diacetate; sodium t-butanolate; In tetrahydrofuran; toluene; at 110℃; for 6h;Inert atmosphere; | A mixture of <strong>[171408-84-7]2,7-dibromo-9,9'-spirobi[fluorene]</strong> (SP, 1 g, 1 equiv.), 10H-phenothiazine (2, 0.88 g,2.1 equiv.), Pd(OAc)2 (0.05 g, 0.1 equiv.), t-Bu3P (10% in toluene, 0.15 mL, 0.03 equiv.), NaOt-Bu(0.81 g, 4 equiv.), and anhydrous toluene (100 mL) were added together and stirred under a nitrogenatmosphere for 6 hours at 110 C. After completion of the reaction, the crude mixture was extractedwith dichloromethane three times. The organic layer was dried over anhydrous sodium sulphate andconcentrated through a rotary evaporation process. The residue was purified by using chloroformand n-hexane solvents through a recrystallization process to achieve SP2 as a yellow solid. Yield: 92%;1H-NMR (500 MHz, CDCl3) delta 8.12-8.14 (d, J = 10 Hz, 2H), 7.75-7.77 (d, J = 10 Hz, 2H), 7.44-7.46 (d, J =10 Hz, 2H), 7.31-7.34 (t, J = 10 Hz, 4H), 7.11-7.14 (t, J = 10 Hz, 4H), 6.87-6.94 (m, 10H), 6.81 (s, 2H),6.08-6.10 (d, 4H); 13C NMR (500 MHz, CDCl3) delta 152.66, 147.34, 141.93, 140.86, 128.34, 128.12, 126.83,126.68, 123.60, 122.21, 120.45, 115.70, 66.18; GC-MS: 710.50 for C49H30N2S2 [M+H+]. |
General procedure: 10H-phenothiazine (2.0 g, 2.2 equiv.), dibromide (1 equiv.),Pd2(dba)3 (1.3 g, 0.3 equiv.) and t-Bu3PHBF4 (0.7 g, 0.5 equiv.) were dissolved in dry and degassed toluene (100 mL). After the mixture wasstirred for 10 min, sodium tert-butoxide (1.0 g, 2.2 equiv.) was addedand the mixture was stirred at 110 C for 24 h. After cooling down toroom temperature, the reaction system was extracted with EtOAc(3×50 mL). The organic layer was then separated and dried over sodiumsulfate (Na2SO4). The solvent was removed under reduced pressureto give a crude product, which was purified by column chromatographywith petroleum ether/dichloromethane (5/1, v/v) as eluent toobtain the final product. 2.1.1.1. 2?,7?-di(10H-phenothiazin-10-yl)spiro[cyclopropane-1,9?-fluorene] (1). Orange yellow solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | With copper(l) iodide; caesium carbonate; ethylenediamine; In toluene; for 24h;Reflux; | Compound D3 (5.97 g, 30.0 mmol), <strong>[221037-98-5]3-iodobenzeneboronic acid</strong> (8.67 g, 35 mmol), cuprous iodide (2.85 g, 15.0 mmol), ethylenediamine (0.90 mg, 15.0 mmol) were sequentially added to the reaction flask. , cesium carbonate (30.0g, 92.0mmol) and toluene(200 mL), stirred under reflux for 24 hours. After the reaction was completed, the reaction mixture was extracted with ethyl acetate.Concentrated under reduced pressure,The obtained crude product was subjected to column purification to yield Compound E3 (7.28 g, 76percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
66.7% | 6.93 g (35 mmol) of thiazideAdd to a 250 ml three-necked flask and add 100 ml of N,N-dimethylformamide as the reaction solvent in an ice bath.Stir on a magnetic stirrer for 10 min. 0.72 g (30 mmol) of NaH was added in portions to the reaction flaskIn the middle, continue stirring for 1 h.Dissolve 2.07 g (10 mmol) of <strong>[3029-64-9]2,4,6-trichloro-5-cyanopyrimidine</strong> in 40 ml of N,N-dimethylformylThe amine solution was added dropwise to the reaction system, and after the addition was completed, the reaction was carried out at room temperature for 24 hours. After the reaction was completed, the reaction solution was poured into 200 ml of 10percent diluted hydrochloric acid, and the mixture was filtered under reduced pressure, washed with water and dried, and the crude product was obtained from petroleum ether and dichloromethane (PE: DCM=10: 1) Pass the column for the mobile phase. 4.64 g of a white solid powder was obtained in a yield of 66.7percent. |
Tags: Phenothiazine | Thiodiphenylamine | Aryls | Dopamine Receptor | Organic-dye Photoredox Catalysts | Organic Building Blocks | Neuronal Signaling | GPCR/G Protein | Parkinson'S Disease and Alzheimer'S Disease | Photoredox Catalysts | 92-84-2
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