Structure of 85279-30-7
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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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Batch number can be found on the product's label following the word 'Batch'.
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CAS No. : | 85279-30-7 |
Formula : | C8H9NO |
M.W : | 135.16 |
SMILES Code : | CC(=O)C1=NC=CC=C1C |
MDL No. : | MFCD08062668 |
InChI Key : | SYISHRLXIIZBHJ-UHFFFAOYSA-N |
Pubchem ID : | 13068669 |
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 |
---|---|---|
With potassium tert-butylate; In tetrahydrofuran; at -20 - 10℃; for 2h; | Dissolve 2-AMINO-4-CHLORONICOTINALDEHYDE (156 mg, 1.0 mmol) and 2-acetyl-3- methylpyridine (136 mg, 1.0 mmol) in anhydrous THF (5.0 mL) and cool it to-20C under N2 atmosphere. Add in portion t-BuOK (224 mg, 2.0 mmol) to the reaction mixture and stir the mixture at 10C for 2 hours. Concentrate the reaction mixture under vacuum, dilute the residue with water (10 mL), filter the solid, wash the solid with water and dry under high vacuum to afford the title product as a yellow colored solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
*2-Bromoacetyl-3-methylpyridine hydrobromide was prepared from <strong>[85279-30-7]2-acetyl-3-methylpyridine</strong> (T.A.Crabb et al., Org. Magn. Reson., 1982, 20 , 242) according to the procedure for preparing 2-bromoacetyl-4-methylpyridine hydrobromide described in step 5 of Example 1. 1H-NMR (DMSO-d6) delta: 8.56 (1H, d, J=3.6Hz), 7.84 (1H, d, J=7.7Hz), 7.56-7.60 (1H, m), 5.01 (2H, s), 4.01 (3H, s). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With sodium hydride; In mineral oil; at 90℃; for 4h; | To a stirred solution of <strong>[85279-30-7]1-(3-methylpyridin-2-yl)ethanone</strong> (500 mg, 3.70 mmol, 1 eq) in diethyl carbonate (30 ml) was added NaH (60% in oil, 887.6 mg, 22.2 mmol, 6 eq) protionwise at 25 oC. The grey suspension was then stirred at 90 oC for 4 hours. Acetic acid (2.1 ml) in diethyl ether (21 ml) was added dropwise to quench the reaction. The resulting mixture was filtered through a pad of celite. The filtrate was concentrated and purified on silica gel (80 g) with a gradient of ethyl acetate in hexanes from 0 : 1 to 3 : 7 to give a dark brown oil (650 mg, 85%). 1H NMR (300 MHz, CDCl3): delta 8.52-8.46 (m, 1H), 7.63-7.59 (m, 1H), 7.35 (dd, J = 7.9, 4.5 Hz, 1H), 4.24-4.10 (m, 4H), 2.63 (s, 3H), 1.23 (t, J = 7.0 Hz, 3H); Calculated for C11H13NO3, 207.09; MS (ESI) (m/z) observed 208.2 (M + 1)+. |
85% | With sodium hydride; In mineral oil; at 25 - 90℃; for 4h; | To a stirred solution of <strong>[85279-30-7]1-(3-methylpyridin-2-yl)ethanone</strong> (500 mg, 3.70 mmol, 1 eq) in diethyl carbonate (30 ml) was added NaH (60% in oil, 887.6 mg, 22.2 mmol, 6 eq) protionwise at 25 C. The grey suspension was then stirred at 90 C for 4 hours. Acetic acid (2.1 ml) in diethyl ether (21 ml) was added dropwise to quench the reaction. The resulting mixture was filtered through a pad of celite. The filtrate was concentrated and purified on silica gel (80 g) with a gradient of ethyl acetae in hexances from 0 : 1 to 3 : 7 to give a dark brown oil (650 mg, 85%). NMR (300 MHz, CDCh): delta 8.52-8.46 (m, 1H), 7.63-7.59 (m, 1H), 7.35 (dd, J = 7.9, 4.5 Hz, 1H), 4.24-4.10 (m, 4H), 2.63 (s, 3H), 1.23 (t, J = 7.0 Hz, 3H); Calculated for CI 1H13N03, 207.09; MS (ESI) (m/z) observed 208.2 (M + 1)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With sodium hydroxide; In methanol;Reflux; | General procedure: A suspension of aldehyde intermediate 4 (0.64 mmol) and ketone 5a-5i (0.64 mmol) in methanol (5 mL) was treated with solid sodium hydroxide (0.83 mmol) and refluxed for 3-4 h. After completion of the process, the precipitated solid was filtered off, washed with water and dried under vacuum to give a pure compounds 6a-6i. |