Structure of 59576-28-2
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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. : | 59576-28-2 |
Formula : | C8H9NO2 |
M.W : | 151.16 |
SMILES Code : | COC1=CC(=NC=C1)C(C)=O |
MDL No. : | MFCD10697664 |
InChI Key : | VYESAHFYMWMHMN-UHFFFAOYSA-N |
Pubchem ID : | 21816816 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-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 |
---|---|---|
2-Acetyl-4-methoxypyridine: The title compound was prepared from 4-methoxy-2-piridinecarbonitrile by using the procedure described for the preparation of 2-acetyl4-chloropyridine. 1H-NMR (CDCl3)δ 8.49 (1H, d, J=5.5 Hz), 7.58 (1H, d, J=2.6 Hz), 6.98 (1H, dd, J=2.6, 5.5 Hz), 3.91 (3H, s), 2.72 (3 H, s). | ||
With manganese(IV) oxide; In chloroform; at 80℃; for 1.0h; | General procedure: Manganese dioxide (233 mg) was added to a solution of N,N-diethyl-2-(4-(6-(hydroxymethyl)pyridin-2-yl)piperazin-1-yl)acetamide (61 mg) obtained in Reference Example 21-1-1 (1) in chloroform (0.7 mL), followed by stirring at 80 C. for 1 hour. The reaction mixture was filtered using Celite, whereby the insoluble materials were removed. The solvent was distilled off under reduced pressure, whereby N,N-diethyl-2-(4-(6-formylpyridin-2-yl)piperazin-1-yl)acetamide (61 mg) was obtained. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | [Referential Example 16]; 1-(4-Methoxy-2-pyridyl)ethanone ; [] In an argon atmosphere, 0.93M methylmagnesium bromide in tetrahydrofuran (13.8 mL) was added dropwise to 4-methoxypyridine-2-carbonitrile (1.56 g) in tetrahydrofuran (31 mL) at -78C, followed by stirring for 15 minutes. Subsequently, the reaction mixture was stirred at 0C for 15 minutes, and then at room temperature for 5 hours. Water was added dropwise to the reaction mixture. The resultant mixture was partitioned between water and ethyl acetate. The organic layer was dried over sodium sulfate anhydrate, followed by filtration. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane - ethyl acetate), to thereby give the title compound as a solid substance (1.30 g, 73%) .1H-NMR(400MHz,CDCl3) δ: 2.72(3H,s), 3.91(3H,s), 6.97-6.99(1H,m), 7.57-7.58(1H,m), 8.48-8.50(1H,m). MS(ESI)m/z: 152(M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
2-(Bromoacetyl)-4-methoxypyridine hydrobromide: 2-(Bromoacetyl)-4-methoxypyridine hydrobromide was prepared from <strong>[59576-28-2]2-acetyl-4-methoxypyridine</strong> according to the method of H. McKennis, Jr., L. B. Turnbull, E. R. Bowman, and E. Tamaki (in J. Org. Chem., 1963, 28, 383-387). 1H-NMR (DMSO-d6) δ: 8.61 (1 H, d, J=5.9 Hz), 7.66 (1 H, dd, J=2.6 Hz), 7.37 (1 H, dd, J=2.6, 5.9 Hz), 5.03 (2H, s), 3.97 (3H, s) | ||
*2-Bromoacetyl-4-methoxypyridine hydrobromide was prepared from <strong>[59576-28-2]2-acetyl-4-methoxypyridine</strong> (B Case et al., J. Org. Chem., 1961, 26 , 4415) according to the procedure for preparing 2-bromoacetyl-4-methylpyridine hydrobromide described in step 5 of Example 1. 1H-NMR (DMSO-d6) δ: 8.59-8.62 (1H, m), 7.63-7.65 (1H, m), 7.33-7.37 (1H, m), 5.03 (2H, s), 3.96 (3H, s). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
3.60 g (60%) | With MeMgI; In benzene; | 2-Acetyl-4-methoxypyridine: To a solution of 4-methoxy-2-pyridinecarbonitrile (5.35 g, 38.6 mmol) in benzene (50 ml) and ether (50 ml) cooled to 0 C. was added dropwise over 20 min a 2M slution of MeMgI in ether (23 ml, 46.3 mmol). After 0.5 h, the mixture was allowed to warm to ambient temperature, and stirring continued for 2 h. The mixture was cooled to 0 C. and 2M aqueous HCI (100 ml) added. The mixture was made basic with saturated aqueous sodium bicarbonate (~80 ml) and the organic layer separated and dried (MgSO4). After removal of solvent, the residue was purified by flash chromatography eluding with ethyl acetate/hexane (1:5) to afford 3.60 g (60%) of 2-acetyl-4-methoxypyridine. 1H-NMR (CDCl3) δ: 8.49 (1 H, d, J=5.5 Hz), 7.58 (1 H, d, J=2.6 Hz), 6.98 (1 H, dd, J=2.6, 5.5 Hz), 3.91 (3H, s), 2.72 (3 H, s) |
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