Structure of 16401-14-2
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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. : | 16401-14-2 |
Formula : | C4H3NO2 |
M.W : | 97.07 |
SMILES Code : | O=CC1=CC=NO1 |
MDL No. : | MFCD07778412 |
InChI Key : | GSIPOZWLYGLXDM-UHFFFAOYSA-N |
Pubchem ID : | 21817604 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302 |
Precautionary Statements: | P280-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 |
---|---|---|
45% | With Dess-Martin periodane; In dichloromethane; at 20℃; for 1.5h; | Step 2Isoxazole-5-carbaldehydeIn a round-bottomed flask, isoxazol-5-yl-methanol (511 mg, 5.16 mmol) was dissolved in dichloromethane (30 ml). Dess-Martin periodinane (2.3 g, 5.41 mmol) was added and the reaction mixture was stirred at room temperature for 1.5 h. The reaction was quenched with 50 ml of a 1 :1 solution of 10%> aqueous Na2S203 and saturated aqueous NaHCC>3 and then extracted with dichloromethane (2x). The organic layers were washed with saturated aqueous NaHCC>3, water and brine. The aqueous layers were back extracted with dichloromethane. The organic layers were combined, dried over sodium sulfate, filtered and concentrated. The residue was chromato graphed over silica gel with EtOAc/hexanes (gradient 0-40% EtOAc) to afford 226 mg (45%) of isoxazole-5-carbaldehyde as a colorless oil. 1H NMR (CDC13, 300 MHz): ? (ppm)10.05 (s, 1H), 8.44 (d, J=1.9 Hz, 1H), 7.02 (d, J=1.9 Hz, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
By reacting any of the following aldehydes: ... 3-furaldehyde, isoxazolyl-3-carboxaldehyde and isoxazole-5-carboxaldehyde |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With diisobutylaluminium hydride; In dichloromethane; at -78℃; for 1h; | Experiment 2If; Isoxazole-S-carboxylic acid, which was commercially available from TCI, was converted to the methyl ester, and then reduced by DIBAL-H to afford the isoxazole-5-carbaldehyde (1.05 g, yield 60 %). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium hydroxide; mesitylenesulfonylhydroxylamine; | EXAMPLE 91 7-Bromo-2-isoxazol-5-yl-[1,2,4]triazolo[1,5-a]pyridin-5-ylamine The title compound, MS m/e (%): 280 (M+, 100), was prepared in accordance with the general method of example 63 from 4-bromo-pyridine-2,6-diamine, O-mesitylene-sulfonylhydroxylamine, and <strong>[16401-14-2]isoxazole-5-carbaldehyde</strong>. The purification was performed with reversed phase HPLC eluting with an acetonitrile/water gradient. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
General procedure: A solution of 19 (300 mg, 0.70 mmol) in tetrahydrofuran (3 mL) was slowly added to a solution of lithium diisopropylamide (LDA) in heptane/tetrahydrofuran/ethylbenzene (2 M, 0.38 mL, 0.76 mmol) at 78oC, and the resultant solution was stirred at -78oC for 30 minutes. Chlorotitanium triisopropoxide (1 M, 2.8 mL) was then added slowly, and the resulting mixture was stirred at 40oC for 1 hour. The reaction was cooled to -78oC, and propionaldehyde (49 mg, 0.84 mmol) was added slowly. This mixture was then warmed to 40oC, and stirred at 40oC for 2 hours. The reaction mixture was quenched with saturated aqueous ammonium chloride solution (1 mL), diluted with 10 mL of tetrahydrofuran, and treated with Celite for 1 hour. The resultant slurry was filtered and concentrated. The resultant residue was purified by silica gel chromatography (gradient: 95:5 hexanes:ethyl acetate to 65:35 hexanes:ethyl acetate) to provide 20 as a white solid. Yield: 230 mg, 68%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
59% | With N-(2,2,2-trifluoroethyl)-1H-imidazole-1-carboxamide; sodium tris(acetoxy)borohydride; In acetonitrile; at 20℃; for 1.5h; | Example 53 N,3-dimethyl-5-({4-[(1R,5S)-8-(1,2-oxazol-5-ylmethyl)-3,8-diazabicyclo[3.2.1]oct-3-yl]pyrimidin-2-yl}amino)pyridine-2-carboxamide To a solution of N-(2,2,2-trifluoroethyl)-1H-imidazole-1-carboxamide (Preparation 82) and 5-((4-((1R,5S)-3,8-diazabicyclo[3.2.1]octan-3-yl)pyrimidin-2-yl)amino)-N,3-dimethylpicolinamide hydrochloride (Preparation 1, 50 mg, 0.12 mmol) and <strong>[16401-14-2]5-isoxazolecarboxaldehyde</strong> (32 mg, 0.33 mmol) in MeCN (1 mL) was added sodium triacetoxyborohydride (76 mg, 0.35 mmol) and the reaction was stirred at room temperature for 1.5 hours. The reaction was quenched by the addition of saturated aqueous NaHCO3 solution and extracted into EtOAc three times. The organic layer was collected, dried over magnesium sulfate and concentrated in vacuo. The residue was purified by silica gel column chromatography eluting with 0-10% MeOH in DCM followed by trituration with diethylether to afford the title compound (30 mg, 59%). LCMS Rt=0.69 minutes; MS m/z 435 [M+H]+ |
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