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CAS No. : | 198821-79-3 | MDL No. : | MFCD03844645 |
Formula : | C10H10N2O2 | Boiling Point : | No data available |
Linear Structure Formula : | - | InChI Key : | KYCMMXMEXWSPCV-UHFFFAOYSA-N |
M.W : | 190.20 | Pubchem ID : | 15462732 |
Synonyms : |
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Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P280-P305+P351+P338 | UN#: | |
Hazard Statements: | H302-H315-H319-H332-H335 | Packing Group: | |
GHS Pictogram: |
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* 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 ethanol; | General procedure: The mixture of the compound 15 (190.2 mg, 1.0 mmol) and 2-thiophenecarboxaldehyde (123.4 mg, 1.1 mol) in anhydrous ethanol (3.0 mL) was stirred over night at room temperature or reflux temperature. The corresponding imine was reduced with solid sodium borohydride (75.7 mg, 2.0 mmol) which was added slowly, the mixture was further stirred over night at room temperature. An additional ethanol (2.0 mL) was added to the reaction vessel after which 10percent hydrochloric acid aqueous solution was added to quench excess sodium borohydride. The acidic mixture was basified with 25percent aqueous ammonia solution. The desired product was extracted with dichloromethane (3 20 mL) and the solution was dried over sodium sulphate anhydrous. The solvent was removed under reduced pressure and the residue was purified by flash chromatography on silica gel, eluting with a gradient of 40-60percent ethyl acetate in petroleum ether to give the title compound 17a1 [164.9 mg, 57.6percent (from 15)] as a white solid, mp 100-101 °C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
54.6% | Dissolve 3-methoxy-4-(oxazol-5-yl) aniline (190.2 mg, 1 mmol) in absolute ethanol (3 ml), add in 5-formyl-2-thiophene-carboxylic acid (1.1 mmol), stir at room temperature until the starting material 3-methoxy-4-(oxazol-5-yl) aniline disappears. Add a reducing agent (e.g. NaBH4, 2 mmol) at 0-10° C., then warm at ambient temperature until the disappearance of the intermediate. Dissolve the mixture under heating with ethanol, filter, and evaporate part of the solvent, let stand the mixture to obtain a yellow solid product 7, yield: 54.6percent. 1H NMR (DMSO-d6, delta) 3.82 (s, 3H, -OCH3), 4.39 (br, 1H, -NH), 4.40 (s, 2H, -CH2-), 6.32 (d, J=8.5 Hz, 1H, 6-Ph), 6.39 (s, 1H, 2-Ph), 6.85 (d, J=3 Hz, 1H, 3-Th); 7.03 (d, J=3.5 Hz, 1H, 4-Th), 7.18 (s, 1H, 4-Ox), 7.37 (d, J=8.5 Hz, 1H, 5-Ph); 8.21 (s, 1H, 2-Ox). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
44% | With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide; at 20℃; for 12h; | To a stirred solution of 3-methoxy-4- (oxazol-5-yl) aniline (75 mg, 0.395 mmol) and 3, 4-dihydro-2H-l-benzopyran-4- carboxylic acid (105.3 mg, 0.592 mmol) in DMF (3 mL) were added DIPEA (0.15 mL) and HATU (226 mg, 0.592 mmol) at room temperature and the reaction was stirred for 12 h at rt. After completion of the reaction, the reaction mixture was purified by preparative HPLC to yield N-(3-methoxy-4- (oxazol-5-yl) phenyl) chromane-4-carboxamide (60.07 mg, 44%). Analytical HPLC Method A. Rt: 1.42 min; MS: 351.2 (M+H) . |
44% | With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide; at 20℃; for 16h; | To a stirred solution of 3-methoxy-4-(oxazol-5-yl)aniline (75 mg, 0.395 mmol) and 3,4-dihydro-2H-1-benzopyran-4- carboxylic acid (105.3 mg, 0.592 mmol) in DMF (3 mL) were added DIPEA (0.15 mL) and HATU (226 mg, 0.592 mmol) at room temperature and the reaction was stirred for 12 h at room temperature. After completion of the reaction, the reaction mixture was purified by preparative HPLC to yield N-(3-methoxy-4-(oxazol-5-yl)phenyl)chromane-4-carboxamide (60.07 mg, 44%). Analytical HPLC Method A. Rt: 1.42 min; MS: 351.2 (M+H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
48% | With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide; at 20℃; for 12h; | To a stirred solution of 3-methoxy-4- (oxazol-5-yl) aniline (75 mg, 0.395 mmol) and 6-methoxy-3, 4-dihydro-2H-l- benzopyran-3-carboxylic acid (123.1 mg, 0.592 mmol) in DMF (3 ioL) were added DIPEA (0.15 mL) and HATU (226 mg, 0.592 mmol) at room temperature and the reaction was stirred for 12 h at rt. After completion of the reaction, the reaction mixture was purified by preparative HPLC to yield 6-methoxy-N- (3-methoxy-4- (oxazol-5-yl) phenyl) chromane-3- carboxamide (72.3 mg, 48%). Analytical HPLC Method A. Rt: 1.55 min; MS: 381.2 (M+H) . |
48% | With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide; at 20℃; for 12h; | To a stirred solution of 3-methoxy-4-(oxazol-5-yl)aniline (75 mg, 0.395 mmol) and 6-methoxy-3,4-dihydro-2H-1- benzopyran-3-carboxylic acid (123.1 mg, 0.592 mmol) in DMF (3 mL) were added DIPEA (0.15 mL) and HATU (226 mg, 0.592 mmol) at room temperature and the reaction was stirred for 12 h at room temperature. After completion of the reaction, the reaction mixture was purified by preparative HPLC to yield 6-methoxy-N-(3-methoxy-4- (oxazol-5-yl)phenyl)chromane-3-carboxamide (72.3 mg, 48%). Analytical HPLC Method A. Rt: 1.55 min; MS: 381.2 (M+H). |
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