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CAS No. : | 234082-35-0 | MDL No. : | MFCD06203675 |
Formula : | C8H6ClFO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | RUTYNTBIMOCJMW-UHFFFAOYSA-N |
M.W : | 188.58 | Pubchem ID : | 17733354 |
Synonyms : |
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H332-H335 | Packing Group: | N/A |
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 |
---|---|---|
With dimethyl sulfoxide; In water; ethyl acetate; | Methyl 3-chloro-4-(piperazin-1-yl)-benzoate Dimethyl sulfoxide (15 ml) was added to 4.5 g of piperazine to prepare a suspension, and 1.1 g of <strong>[234082-35-0]methyl 3-chloro-4-fluorobenzoate</strong> was added to the suspension. The mixture was heated to 80 C., and was stirred for 5 hr. The mixture was then cooled to room temperature. Ethyl acetate (1,000 ml) and 500 ml of water were added thereto. The organic layer was separated, dried over anhydrous magnesium sulfate, and concentrated under the reduced pressure. The residue was purified by column chromatography on silica gel (development system: methylene chloride-methanol=5:1) to prepare 905 mg of the title compound. Physicochemical Properties of Intermediate 31 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With dimethyl sulfoxide; In water; ethyl acetate; | Intermediate 46: Methyl 3-chloro-4-(4-hydroxypiperidin-1-yl)benzoate Dimethyl sulfoxide (10 ml) was added to 2.6 g of 4-hydroxypiperidine to prepare a solution. Methyl 3-chloro-4-fluorobenzoate (6.2 g) was added to the solution. The mixture was stirred at 120 C. for 2 hr. The reaction solution was then cooled to room temperature, and poured into 2,000 ml of water, followed by extraction twice with 1,000 ml of ethyl acetate. The combined organic layer was dried over anhydrous magnesium sulfate, and then concentrated under the reduced pressure to prepare 5.8 g of the title compound. Physicochemical Properties of Intermediate 46 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate; In acetonitrile; at 160℃; for 0.5h;Microwave irradiation; | Methyl 3-chloro-4-({3-[(1-methylethyl)oxy]-5-[(1,3-thiazol-2-ylamino)carbonyl]phenyl} oxy) benzoate; To a solution of 3-hydroxy-5-[(1-metl1ylethyl) oxy]-N-1, 3-thiazol-2-ylbenzamide (208 mg) and <strong>[234082-35-0]methyl 3-chloro-4-fluorobenzoate</strong> (141 mg) in acetonitrile (5 mL) was added potassium carbonate (104 mg) and the stirred mixture heated at 160C in a'Smith Creator Microwave' for 30 minutes. The mixture allowed to return to ambient temperature and pressure, the acetonitrile evaporated, and the residue partitioned between ethyl acetate (50 mL) and water (20 mL). The organic layer was separated, washed with brine, dried (MgS04), and evaporated to a residue which was chromatographed on silica, eluting with 30% ethyl acetate in isohexane, to give the desired ester (178 mg). 'H NMR 8 (CDC13) : 1.3 (d, 6H), 3.9 (s, 3H), 4.5-4. 6 (m, 1H), 6.75 (t, 1H), 6.95 (d, 1H), 7.0 (d, 1H), 7.1 (s, 1H), 7.2 (m, 1H), 7.3 (s, 1H), 7.9 (dd, 1H), 8. 05 (d, 1H) ; m/z 447 (M+H) + |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate; In acetonitrile; at 160℃; for 0.5h;Microwave; | The required esters for Example 18 & 18a-e were prepared as described below:; Methyl 3-chloro-4-(3-[(1S)-2-methoxy-(1-methylethyl)oxy]-5-[(1-methyl-1H-pyrazol-3- yl)amino]carbonyl}phenoxy)benzoate; To a solution of 3-hydroxy-5-[(1 S)-2-methoxy-(1-methylethyl) oxy]-N-(l-methyl-lH-pyrazol- 3-yl) benzamide (832 mg, 2.72 mmol) and methyl-3-chloro-4-fluorobenzoate (504 mg, 2.72 mmol) in acetonitrile (20 mL) was added potassium carbonate (364 mg, 2.72 mmol) and the stirred mixture heated at 160C in a'Smith Creator Microwave'for 30 minutes. The mixture was allowed to return to ambient temperature and pressure, filtered and evaporated to a residue which was chromatographed on silica with 0-50% ethyl acetate in hexane as eluant to give the desired compound (1.11 g). m/z 474 (M+H) + |
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