Structure of 92901-88-7
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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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CAS No. : | 92901-88-7 |
Formula : | C6H7NO2 |
M.W : | 125.13 |
SMILES Code : | O=CC1=C(C)OC(C)=N1 |
MDL No. : | MFCD03923827 |
InChI Key : | MLYKOGIEABSYKL-UHFFFAOYSA-N |
Pubchem ID : | 7537478 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H319 |
Precautionary Statements: | P337+P313-P305+P351+P338-P264-P280 |
* 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 |
---|---|---|
In diethyl ether; at 20℃; for 1h; | Preparation 49 l-(2,5-dimethyloxazol-4-yl)ethanol To a solution of <strong>[92901-88-7]2,5-dimethyloxazole-4-carbaldehyde</strong> (1 g, 7.99 mmol) in ether (26.6 ml) at rt was added methylmagnesium bromide (7.99 ml, 1 1.19 mmol) dropwise, and the reaction mixture was stirred at rt for 1 h. Hydrochloric acid ( 11.19 ml, 1 1.19 mmol) was added, and the aqueous layer was extracted with EtOAc (x3). The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, and filtered, and the filtrate was evaporated in vacuo to give the crude product (1.2 g, 100%). This crude product was used without purification. XH NMR (500MHz, CHLOROFORM-d) δ 4.79 (quin, J=6.4 Hz, 1H), 2.41 (s, 3H), 2.30 (s, 3H), 1.53 (d, J=6.6 Hz, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Example 1.1.10: l-( 2,5-dimethyloxazol-4-yl ) -N-methylmethanamine[0287] Ti(0,PR)4 (1. 08 mL, 3.69 mmoles) was added with stirring to MeNH2 ( 4.3 mL, 2.0 M in MeOH, 8.5 mmoles ) at 0 C under Ar. After 15 min the aldehyde ( 360 mg, 2. 83 mmoles) was added, and the reaction was stirred for 2-3 h. NaBH4 (139 mg, 3.69 mmoles) was added in batches, and the reaction was stirred at 0 C to RT overnight. The solvent was removed via rotary evaporation. The residue was diluted with water/CH2Cl2. A white ppt formed and was removed via filtration through Celite. The layers were separated. The aqueous layer was extracted with CH2C12 (x3) and the combined organics were dried over Na2S04. The inorganics were filtered off, and the solvent was removed via rotary evaporation to give 300 mg of l-(2,5-dimethyloxazol-4-yl)-N-methylmethanamine. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
55% | [007441 To a stirred solution of 2,5-dirnethyloxazole-4-carbaldehyde (272 mg, 2.17 mrnol) and ammonium carbonate (564 mg, 5.87 rnrnol) in EtOH (6 rnL) and water (2 mL) at 50C was added dropwise over 20 minutes a solution of potassium cyanide (177 mg, 2.72 mnol) in water (3.8 mL). The solution was stirred at 60C for 16 h. The EtOH was distilled off at 80C and HC1 added (0.2 rnL of a 37% aqueous solution). The mixture was allowed to cool to room temperature and the precipitate collected by filtration, washing successively with water (5 rnL) and iso-hexanes (2 x 5 mL). This was dissolved in MeOH (14 mL) with stirring and treated with potassium hydroxide (5.2 mL of a 2.5 M aqueous solution, 13.1 rnrnol) and the solution stirred at 60C for 100 h. The mixture was allowed to cool and acidified with HC1. Solvents were evaporated and the residue treated with MeOH (10 rnL). The mixture was filtered and the filtrate evaporated to afford 205 mg (55%) of 2-arnino-2-(2,5-dirnethyloxazol-4-yl)acetic acid hydrochloride as an orange oil. LCMS-ESI (ni/z) calculated for C7H10N203: 170.1; found 171.1 [M±H],tR = 0.23 mm (Method 1i).’H NMR (400 MHz, DMSO) 8.71 (br s, 3H), 5.13 (s. 1H), 2.38 (s, 3H), 2.34 (s, 3H). |
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