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CAS No. : | 1877-71-0 | MDL No. : | MFCD00029972 |
Formula : | C9H8O4 | Boiling Point : | No data available |
Linear Structure Formula : | - | InChI Key : | WMZNGTSLFSJHMZ-UHFFFAOYSA-N |
M.W : | 180.16 | Pubchem ID : | 601880 |
Synonyms : |
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Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | |
Hazard Statements: | 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 |
---|---|---|
82% | With methanol; triethylamine;palladium diacetate; 1,3-bis-(diphenylphosphino)propane; at 100℃; under 25858.1 Torr; for 15h; | The following were introduced into a vessel: [10.] Og (40.3 mmol) of <strong>[618-89-3]methyl 3-bromobenzoate</strong>, 2.5g (mmol) of 1, 3-bis (diphenylphosphino) propane ("DPPP"), 14 mL of triethylamine, 0.905 g of palladium acetate, and 140 ml of methanol. The vessel was sealed and pressurized with carbon monoxide to a pressure of 500 psi. The vessel was heated to [100 C] for 15 hours. The mixture was then cooled and concentrated on a rotary evaporator before partitioning between EtOAc and 2M HC1. The layers were separated, and the aqueous layer was extracted with EtOAc [(LX).] The organic extracts were combined and washed with saturated aqueous [NACL] solution and dried [(MGSO4).] Concentration provided a solid, which is slurred in hexane and filtered. The material is dried in a vacuum oven at- 10mmHg at [70 C] ; yield 5.9g [(82%).] NMR: [DMSO'H 8] (ppm) 3.54 (3H, s); 7. [18-7.] 21 [(1H,] m); 7. [34- 7.] 40 [(1H,] m); 7. 46- 7.49 (1H m); 7. [87- 7.] 89 [(1H,] m). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | Example 169 Amethyl 3-(4-(cyclopropanecarbonyl)piperazine-1-carbonyl)benzoate; To a solution of 3-(methoxycarbonyl)benzoic acid (0.9 g, 5 mmol) in dichloromethane (20 mL), 1-hydroxybenzotriazole (0.75 g, 5.5 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (1.06 g, 5.5 mmol) and triethyl amine (2 mL) were added. The mixture was stirred at room temperature for 30 min, and then <strong>[59878-57-8]cyclopropyl(piperazin-1-yl)methanone</strong> (1.0 g, 5 mmol) was added and the mixture was stirred at room temperature for 16 h. The resulting mixture was added water (50 mL) and extracted with dichloromethane (100 mL×3), the organic phase was washed with sodium bicarbonate, brine and concentrated. The crude product was purified by column chromatography (silica gel, petroleum ether/ethyl acetate 20:1 to 2:1), 0.95 g of methyl 3-(4-(cyclopropanecarbonyl)piperazine-1-carbonyl)benzoate as an oil was obtained, Yield 60%. 1H-NMR (400 MHz, CDCl3) 0.80-0.82 (m, 2H), 1.00-1.04 (m, 2H), 1.24-1.27 (m, 1H), 3.25-3.78 (m, 8H), 3.94 (s, 3H), 7.52-7.55 (t, J=7.6 Hz, 1H), 7.63-7.65 (d, J=7.6 Hz, 1H), 8.09-8.14 (m, 2H); LC-MS (ESI) m/z: 317(M+1)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃; | <strong>[777-12-8]6-(trifluoromethyl)benzo[d]thiazol-2-amine</strong> (commercially available or prepared according to Step 1 and 2 of Example 1) (1 eq), 3-(methoxycarbonyl)benzoic acid (1.05eq) and DIPEA (5 eq) were dissolved in DMF (2 ml). HI3TU(1.2 eq) was added and the reaction were stirred overnightat ambient temperature before extraction with ethylacetate,washed thoroughly 2 times with dilute acid and dried. Thecrude product, methyl 3-((6-(trifluoromethyl)benzo[d]thi-azol-2-yl)carbamoyl)benzoate, was isolated by evaporationof the solvent under reduced pressure. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 25.0℃; for 16h; | General procedure: To a solution of 7c (45mg, 0.215mmol) in dry CH2Cl2 (2mL), N-(3-dimethylaminopropyl)-N’-ethylcarbodiimide hydrochloride (EDCI) (62mg, 0.322mmol), and 1-hydroxybenzotriazole hydrate (HOBt) (50mg, 0.322mmol) were added followed by amine 10a (27mg, 0.215mmol) and diisopropylethylamine (225μL, 1.290mmol). The reaction mixture was stirred at 25C for 16h then CH2Cl2 was added and the resulting solution was washed with saturated aqueous NH4Cl and water. The organic layers were dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (EtOAc/n-hexane 1:4) |
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