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CAS No. : | 181139-49-1 | MDL No. : | MFCD09038520 |
Formula : | C16H16N2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | NWDYSRZJOLDMRE-QDIHITRGSA-N |
M.W : | 236.31 | Pubchem ID : | 2794493 |
Synonyms : |
|
Signal Word: | Danger | Class: | 9 |
Precautionary Statements: | P501-P273-P260-P270-P264-P280-P391-P314-P337+P313-P305+P351+P338-P301+P312+P330 | UN#: | 3077 |
Hazard Statements: | H302-H319-H372-H410 | Packing Group: | Ⅲ |
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 |
---|---|---|
80% | With sulphate sodium salt In chloroform for 24h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
53% | With triethylamine In dichloromethane at 0 - 20℃; for 4h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In dichloromethane at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine In dichloromethane at 0℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine In dichloromethane at 0℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine In dichloromethane at 0℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine In dichloromethane at 0℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine In dichloromethane at 0℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine In dichloromethane at 0℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | With triethylamine In dichloromethane at 0 - 20℃; for 1h; | 2 4.2. (R,R)-11-(2-Pyridinesulfonamido)-12-amino-9,10-dihydro-9,10-ethanoanthracene 14 A solution of 2-pyridinesulfonyl chloride (0.641 g, 3.61 mmol) in CH2Cl2 (10 mL) was slowly added to a solution of (R,R)-ethanoanthracene diamine (0.853 g, 3.61 mmol) and triethylamine (0.750 mL, 0.547 g, 5.41 mmol) in CH2Cl2 (30 mL) at 0 °C. After the addition was complete, the mixture was warmed to room temperature and stirred for 1 h. The reaction was quenched with water and extracted with CH2Cl2 (3 * 20 mL). The organic phase was dried over anhydrous sodium sulfate and the solvent was removed at reduced pressure. The residue was purified by column chromatography on deactivated silica gel (Et3N/SiO2 = 2.0% v/w, EtOAc/MeOH 9:1) to afford the product (71%) as a white solid. White solid, mp 209-211 °C. [α]D20 = -31.4 (c 1.0, CHCl3). 1H NMR (200 MHz, CDCl3): δ 2.87 (t, J = 2.8 Hz, 1H), 3.33 (t, J = 2.8 Hz, 1H), 4.06 (d, J = 2.8 Hz, 1H), 4.14 (d, J = 2.6 Hz, 1H), 7.05-7.31 (m, 9H), 7.43-7.49 (m, 2H), 7.80-7.99 (m, 2H), 8.61-8.65 (m, 2H). 13C NMR (50 MHz, CDCl3): δ 50.6, 51.9, 60.8, 64.3, 121.7, 124.0, 124.1, 125.7, 125.8, 126.1, 126.2, 126.4, 126.5, 137.3, 137.6, 141.5, 149.4, 157.6. IR (KBr) νmax 3345, 3282, 3023, 2961, 2824, 2791, 2708, 1732, 1581, 1484, 1460, 1426, 1387, 1324, 1281, 1240, 1169, 1127, 1100, 1985, 1060, 1023 cm-1. HRMS (FAB+) m/z calcd for [C21H20N3O2S]: 378.1276, found 378.1266. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: triethylamine / dichloromethane / 0 °C 2.1: chloroformic acid ethyl ester; triethylamine / tetrahydrofuran / 0.5 h / 0 °C 2.2: 2 h / 0 °C 3.1: trifluoroacetic acid / dichloromethane / 24 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: triethylamine / dichloromethane / 1 h / 0 - 20 °C 2.1: chloroformic acid ethyl ester; triethylamine / tetrahydrofuran / 0.5 h / 0 °C 2.2: 2 h / 0 °C 3.1: trifluoroacetic acid / dichloromethane / 24 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: triethylamine / dichloromethane / 0 °C 2.1: chloroformic acid ethyl ester; triethylamine / tetrahydrofuran / 0.5 h / 0 °C 2.2: 2 h / 0 °C 3.1: potassium carbonate / acetone / 4 h / Reflux 4.1: trifluoroacetic acid / dichloromethane / 24 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: triethylamine / dichloromethane / 0 °C 2.1: chloroformic acid ethyl ester; triethylamine / tetrahydrofuran / 0.5 h / 0 °C 2.2: 2 h / 0 °C 3.1: sodium tetrahydroborate / methanol / 1.5 h / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: triethylamine / dichloromethane / 0 °C 2.1: chloroformic acid ethyl ester; triethylamine / tetrahydrofuran / 0.5 h / 0 °C 2.2: 2 h / 0 °C 3.1: trifluoroacetic acid / dichloromethane / 24 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: triethylamine / dichloromethane / 0 °C 2.1: chloroformic acid ethyl ester; triethylamine / tetrahydrofuran / 0.5 h / 0 °C 2.2: 2 h / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: triethylamine / dichloromethane / 0 °C 2.1: chloroformic acid ethyl ester; triethylamine / tetrahydrofuran / 0.5 h / 0 °C 2.2: 2 h / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: triethylamine / dichloromethane / 0 °C 2.1: chloroformic acid ethyl ester; triethylamine / tetrahydrofuran / 0.5 h / 0 °C 2.2: 2 h / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: triethylamine / dichloromethane / 0 °C 2.1: chloroformic acid ethyl ester; triethylamine / tetrahydrofuran / 0.5 h / 0 °C 2.2: 2 h / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: triethylamine / dichloromethane / 0 °C 2.1: chloroformic acid ethyl ester; triethylamine / tetrahydrofuran / 0.5 h / 0 °C 2.2: 2 h / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: triethylamine / dichloromethane / 1 h / 0 - 20 °C 2.1: chloroformic acid ethyl ester; triethylamine / tetrahydrofuran / 0.5 h / 0 °C 2.2: 2 h / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: triethylamine / dichloromethane / 0 °C 2.1: chloroformic acid ethyl ester; triethylamine / tetrahydrofuran / 0.5 h / 0 °C 2.2: 2 h / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: triethylamine / dichloromethane / 0 °C 2.1: chloroformic acid ethyl ester; triethylamine / tetrahydrofuran / 0.5 h / 0 °C 2.2: 2 h / 0 °C 3.1: potassium carbonate / acetone / 4 h / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: triethylamine / dichloromethane / 0 °C 2.1: chloroformic acid ethyl ester; triethylamine / tetrahydrofuran / 0.5 h / 0 °C 2.2: 2 h / 0 °C 3.1: trifluoroacetic acid / dichloromethane / 24 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: triethylamine / dichloromethane / 0 °C 2.1: chloroformic acid ethyl ester; triethylamine / tetrahydrofuran / 0.5 h / 0 °C 2.2: 2 h / 0 °C 3.1: trifluoroacetic acid / dichloromethane / 24 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: triethylamine / dichloromethane / 0 °C 2.1: chloroformic acid ethyl ester; triethylamine / tetrahydrofuran / 0.5 h / 0 °C 2.2: 2 h / 0 °C 3.1: trifluoroacetic acid / dichloromethane / 24 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate In toluene at 85℃; Schlenk technique; Inert atmosphere; | General Procedure (Scheme 2): General procedure: To an oven-dried Schlenk flask were added diamine 3 (1.0 equiv),Pd2(dba)3 (5 mol%), rac-BINAP (10 mol%), NaOtBu (3.0 equiv), and toluene under Ar atmosphere.Then 8-haloqunoline 4 (2.2 equiv) was added directly. The flask was sealed, and the reaction wasstirred at 85 °C until the complete consumption of the starting material 3. The mixture was cooled toroom temperature, filtered through a silica plug, and the plug was washed with EA. The combinedfiltrates were concentrated under reduced pressure, and the residue was purified by silica gelchromatography to give the desired product Ln. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate In toluene at 90℃; Inert atmosphere; |
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