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CAS No. : | 280566-45-2 | MDL No. : | MFCD01862658 |
Formula : | C7H3ClF3NO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | DXRBTBMFFGEVCX-UHFFFAOYSA-N |
M.W : | 225.55 | Pubchem ID : | 2778210 |
Synonyms : |
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Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P301+P312-P302+P352-P304+P340-P305+P351+P338 | UN#: | |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | |
GHS Pictogram: |
* 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 |
---|---|---|
28% | With dmap; triethylamine; In tetrahydrofuran; dichloromethane; | 2. Preparation of 2-chloro-N-(5-ethyl-1,3,4-oxadiazol-2-yl)-6-(trifluoromethyl)nicotinamide (Ex. No. 7-3) 200 mg (0.887 mmol) of 2-chloro-6-(trifluoromethyl)nicotinic acid and 100 mg (0.887 mmol) of 5-ethyl-1,3,4-oxadiazol-2-amine are dissolved at RT in 8 ml of CH2Cl2. Then 846 mg (1.33 mmol) of 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane 2,4,6-trioxide (50% solution in THF) are added, the mixture is stirred at RT for one hour and then 0.618 ml (4.43 mmol) of triethylamine, 22 mg (0.177 mmol) of 4-dimethylaminopyridine are added. The reaction mixture is stirred at RT for 20 h and then washed twice with 4 ml each time of water, dried over sodium sulfate and concentrated. The residue is purified by column chromatography (prep. HPLC; acetonitrile/water). Yield 80 mg (28%). 1H NMR (400 MHz; DMSO-d6): 12.59 ppm (s broad 1H); 8.49 (d, 1H), 8.11 (d, 1H), 2.85 (q, 2H), 1.28 (t, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
51.3% | With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In chloroform; at 20℃; for 96h; | A mixture of HBTU (185 mg, 0.490 mmol), DIPEA (170 gL, 0.980 mmol), 2- chloro-6-(trifluoromethyl)pyridine-3-carboxylic acid (100 mg, 0.440 mmol) and 3- methylsulfonylaniline (79.7 mg, 0.470 mmol) in chloroform (5 mL) was stirred at room temperature for 4 days (for convenience). The contents were treated with 5% Na2C03 and extracted with CHCb (3x). The organic extracts were combined and the solvent removed in vacuo to give a residue which was purified by automated normal- phase chromatography (0-100% EtO Ac/heptane, 12 g silica gel cartridge) to give 2- chloro-N-(3-methylsulfonylphenyl)-6-(trifluoromethyl)pyridine-3-carboxamide (86.2 mg, 0.229 mmol, 51.3 % yield) as ayellow solid. MS, ES+m/z 379.0 [M+H]+. -NMR (400 MHz, DMSO-rie) 5 11.19 (s, 1 H), 8.48 (d, J=7.83 Hz, 1 H), 8.37 (t, J=l .77 Hz, 1 H), 8.17 (d, J=7.58 Hz, 1 H), 7.92 (dt, J=7.7l, 1.83 Hz, 1 H), 7.72 - 7.76 (m, 1 H), 7.67 - 7.72 (m, 1 H), 3.25 (s, 3 H). |