Structure of 1352925-73-5
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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.
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CAS No. : | 1352925-73-5 |
Formula : | C13H15NO |
M.W : | 201.26 |
SMILES Code : | O=C1C(C2)CC2CN1CC3=CC=CC=C3 |
MDL No. : | MFCD21099569 |
InChI Key : | ZVTFKRPHPDTFOT-UHFFFAOYSA-N |
Pubchem ID : | 71743005 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P280-P301+P312-P302+P352-P305+P351+P338 |
* 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 |
---|---|---|
93% | With lithium hexamethyldisilazane; In tetrahydrofuran; tert-butyl alcohol; at -20℃; for 1.0h; | (±) Compound 6(3.2 g, 9.72 mmol) was dissolved in anhydrous THF (5 mL) and LHIVIDS (1M soln./THF, 9.72 mL) was added at -20C. The solution was stirred for one hour before being quenched with H20 (15 mL). EtOAc (20 mL) was added and the organic layer was separated. The aqueous layer was extracted with EtOAc (3 x 15 mL). The organic layers were combined, dried over Mg504 and concentrated in vacuo. The crude oil was filtered through a short silica column (cyclohexane/EtOAc, 2:1) to give Compound 7(1.82 g, 93% yield) as a yellow/orange oil. (Rf=0.24, cyclohexane/EtOAc, 50:50). H (500 MFIz; CDC13) 7.36-7.22 (5H, m, PhH), 4.61 (2H, s,PhCH2), 3.26 (2H, d, J= 1.5, NCH2), 2.84 (1H, q, J = 5.7 Hz, C=OCH), 2.72-2.65 (1H, m,NCH2CI]), 2.38-2.28 (2H, m, C=OCH(CHH)2, 1.73-1.63 (2H, m, C=OCH(CHJ])2 C (126IVIFIz; CDC13) 175.7, 137.4, 128.5, 128.0, 127.2, 50.0, 48.0, 41.1, 33.2, 30.9; m/z (ES) 202.1222(M+W C13H16N0 requires 202.1232). |
65.6% | With lithium hexamethyldisilazane; In tetrahydrofuran; at -20℃; for 1.5h;Inert atmosphere; | To a solution of 12-S5 (1.5 g, 4.56 mmol) in THF (45 mL) under an atmosphere of nitrogen was added LiHIVIDS (1 M solution in THF, 13.68 mL, 13.68 mmol) at -20 CC. The reaction mixture was stirred at -20 C for 1.5 hours under an atmosphere of nitrogen. The reaction mixture was quenched by addition of water5 and extracted with EtOAc (50 mL). The organic phase was washed with brine, dried with anhydrous Na2SO4, and concentrated. The remaining residue was purified by column chromatography on silica gel (eluted with PE/EtOAc = 8:1) to afford the title compound (600 mg, 65.5% yield) as a colorless oil. LC/MS (ESI) m/z: 202 (M+H)t |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | With ammonia; lithium; In tetrahydrofuran; tert-butyl alcohol; at -78℃; | Compound 7 (1.5 g, 7.45 mmol) was dissolved in anhydrous THF/tBuOH, 10:1(10 mL) and the mixture was added to a stirring liquid ammonia at -78 C. Metallic Li pellets were added slowly to the stirring solution until a constant blue/black colour was observed. The reaction was then quenched by the addition of solid ammonium chloride. After removal of the NH3, EtOAc (30 mL) and H20 (8 ml) were added. The organic layer was separated and the aqueous layer was extracted with EtOAc (3 x 15 mL). The organic layers were combined, dried over Mg504 and concentrated in vacuo. The crude oil was filtered through a short silica column (cyclohexane/EtOAc, 1:1) to give Compound 8(800mg, 94% yield) as a yellow oil. (Rf= 0.1, cyclohexane/EtOAc, 50:50). H (500 IVIFIz; CD3OD) 7.46-7.13 (1H, m, NH) 3.43 (2H, d, J= 2.0, NCH2), 2.8 1-2.71 (1H, m, NCH2CI]), 2.60 (1H, q, J=5.6 Hz, C=OCH), 2.48-2.37 (2H, m, C=OCH(CHH)2, 1.70-1.62 (2H, m, C=OCH(CHJ])2). C (126 IVIFIz; CD3OD) 181.5, 46.3, 42.0, 34.3, 31.4; m/z (EI+) 111.0684 (M+W C6H9NO requires 111.0684). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
53.7% | With borane-THF; In tetrahydrofuran; at 0 - 20℃; for 3.0h;Inert atmosphere; | To a solution of 12-S6 (600 mg,2.99 mmol) in THF (45 mL) under an atmosphere of nitrogen was added BH3•THF (1 M solutionin THF, 8.97 mL, 8.97 mmol) at 0 C. The reaction mixture was stirred at room temperature for 3 hours under an atmosphere of nitrogen. The reaction mixture was quenched with MeOH at 0 C and concentrated. The remaining residue was diluted with EtOH (4.5 mL) and water (0.5 mL) and then stirred at 100 C for 3 hours. The mixture was concentrated, diluted with EtOAc, and washedwith water and brine. The organic phase was dried over anhydrous Na2SO4 and concentrated to dryness. The remaining residue was purified by column chromatography on silica gel (eluted with DCM/MeOH = 50:1) to afford the title compound (300 mg, 53.7% yield) as a colorless oil. LC/MS (ESI) m/z: 188 (M+H). |
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