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CAS No. : | 21615-34-9 | MDL No. : | MFCD00000664 |
Formula : | C8H7ClO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | RZNHSEZOLFEFGB-UHFFFAOYSA-N |
M.W : | 170.59 | Pubchem ID : | 88969 |
Synonyms : |
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Signal Word: | Danger | Class: | 8 |
Precautionary Statements: | P261-P280-P305+P351+P338-P310 | UN#: | 3265 |
Hazard Statements: | H227-H314-H335 | Packing Group: | Ⅱ |
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 triethylamine; In dichloromethane; | 2-Methoxy-benzoyl chloride was condensed with 5-Amino-2-nitrobenzotrifluoride in dichloromethane in presence of triethylamine as acid scavenger to yield 2-Methoxy-N-(4-nitro-3-trifluromethyl-phenyl)-benzamide. The reaction mixture was then concentrated in vacuo and the residue was extracted into ethyl acetate. The ethyl acetate layer was washed with water and with cold aqueous hydrochloric acid, then dried over sodium sulphate and finally concentrated in vacuo. The residue obtained was chromatographed over silica gel to afford the desired product. 1H-NMR:delta6.95-8.10 (7H,aromatic), delta3.73(3H,t,Methyl). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | In 1-methyl-pyrrolidin-2-one; at 120℃;Microwave irradiation; | General procedure: In a 35 mL microwave tube equipped with a magnetic stirrer, aminomalononitrile 4-toluenesulfonate (127 mg, 0.50 mmol), N-methylpyrrolidone (5 mL) and thiophene-2-carbonyl chloride (0.09 mL, 0.60 mmol) were added. The vessel was then sealed using a rubber microwave septum and then placed into the microwave cavity. The reaction mixture was irradiated with 200 W of power and heated to 120C (dynamic profile with cooling). When at 120C it was held by moderation of the power. The vessel was then cooled to rt. The reaction mixture was extracted with ethyl acetate (20 mL) and was initially washed with deionised water (2x15 mL), followed by sat. Na2CO3 (2x15 mL). The organic layer was then dried with MgSO4, filtered then evaporated. Using a combiflash R75 the crude reaction mixture was purified using 1:4 ethyl acetate/ methylene chloride as the elutant to give 4a (91 mg, 94% yield) as a white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | In pyridine; at 0 - 20℃; for 16.7h; | [00305] Synthesis of 2-(2-METHOXY-PHENYL)-7-METHYL-3H-QUINAZOLIN-4-ONE m 00 Pyridine, 16h, rtII' nu NHCH /-P [00306] N- (2-CYANO-5-METHYL-PHENYL)-2-METHOXY-BENZAMIDE 2-AMINO-4-METHYL anthronitrile (50. 0G, 378. 3MMOL) was dissolved in 1L dry pyridine and cooled to 0C. O-Anisoyl chloride (63. 0ml, 453. 96MMOL) was added dropwise over a 40 minute period and the reaction was allowed to warm to room temperature and stirred under a nitrogen atmosphere for 16 hours. The reaction was poured over 2L of ice and the product formed a precipitate. The product was collected by vacuum filtration and dried for 3 days to produce the desired product a fluffy tan solid. Recovered 92. 0g 91% yield. LC/MS (10-99%) M/Z 267.2, retention time 3.34 minutes. |
90% | With triethylamine;dmap; In dichloromethane; at 0 - 40℃; for 4h; | To a stirred solution of 4-methyl-2-aminobenzonitrile (100 g, 0.75 mol) in 800mL CH2CI2 was added triethylamine (77.4 g, 0.76 mol) and dimethylaminopyridine (4.62 g, 0.037 mol). The solution was cooled to 0-5 C, and o-anisoyl chloride (129 g, 0.75 mol) was added over 1 h while maintaining the reaction temperature at 0-5 C. The reaction was then stirred at 30-40 C for 3 h. Water (400 mL) was added, and the mixture was stirred for 15 minutes. The organic layer was separated, and the aqueous solution was extracted with CH2CI2 (600 mL). The combined organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo to yield a solid residue, to which 800 mL hexane were added. The slurry was stirred and filtered to give 7V-(2-cyano-5-methyl-phenyl)-2-methoxy-benzamide as a yellow powder (180 g, 90%). mp 147-149 C. .H NMR (CDCI3) 6 2.429 (s, 3H), 4.2 (s, 3H), 6.8-7.2 (m, 3H), 7.4-7.6 (m, 2H), 8.2-8.4 (d, 1H), 8.6 (s, 1H), 10.8 (bs, 1H); 13C NMR (CDCI3) 5 22.68, 55.7, 99,111.27, 116.7,120.3, 121.1,124.15, 131.7, 132.25, 133.67,141.32, 141.1, 157.2,163. M/z(obs., [m+H]+) = 268. |
90% | With dmap; triethylamine; In dichloromethane; at 0 - 40℃; for 4h; | N-(2-Cyano-5-methyl-phenyl)-2-methoxy-benzamide To a stirred solution of 4-methyl-2-aminobenzonitrile (100 g, 0.75 mol) in 800 mL CH2Cl2 was added triethylamine (77.4 g, 0.76 mol) and dimethylaminopyridine (4.62 g, 0.037 mol). The solution was cooled to 0-5 C., and o-anisoyl chloride (129 g, 0.75 mol) was added over 1 h while maintaining the reaction temperature at 0-5 C. The reaction was then stirred at 30-40 C. for 3 h. Water (400 mL) was added, and the mixture was stirred for 15 minutes. The organic layer was separated, and the aqueous solution was extracted with CH2Cl2 (600 mL). The combined organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo to yield a solid residue, to which 800 mL hexane were added. The slurry was stirred and filtered to give N-(2-cyano-5-methyl-phenyl)-2-methoxy-benzamide as a yellow powder (180 g, 90%). mp 147-149 C. 1H NMR (CDCl3) delta 2.429 (s, 3H), 4.2 (s, 3H), 6.8-7.2 (m, 3H), 7.4-7.6 (m, 2H), 8.2-8.4 (d, 1H), 8.6 (s, 1H), 10.8 (bs, 1H) ppm; 13C NMR (CDCl3) delta 22.68, 55.7, 99, 111.27, 116.7, 120.3, 121.1, 124.15, 131.7, 132.25, 133.67, 141.32, 141.1, 157.2, 163. M/z (obs., [m+H]+)=268. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With triethylamine; In 1,4-dioxane; at 20℃; for 2h; | C02H CONH 1, 4.-Dioxn, Etf F3C-''N H F3C'aNH2 NH /r, 2h 0 0 [00302] 2- (2-METHOXY-BENZOYLAMINO)-4-TRIFLUOROMETHYL-BENZOIC acid 2-Amino-4-trifluoro- benzoic acid (3.84g, 18. 73mmol) was dissolved in 30ML dry 1, 4-Dioxane followed by the slow addition of O-Anisoyl chloride (3. 3M1, 24. 35MMOL), then triethylamine (7. 85ml, 56. 19mmol) and stirred under a nitrogen atmosphere at room temperature for 2 hours. Solvent was remove under reduced pressure and organic was partitioned between water and EtOAc and the pH was adjusted to 3 with HC1. Organic layer was separated, dried over MGS04, filtered and concentrated to an off white solid. Recovered 6.35g 100% yield. LC/MS (10-99%) M/Z 339.9, retention time 3. 58 minutes. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine; In dichloromethane; | 2-Methoxy-6-pentadecyl-benzoyl chloride was condensed with 4-Amino-2-trifluromethyl benzonitrile in dichloromethane in presence of triethylamine as acid scavenger to yield N-(4-Cyano-3-trifluoromethyl-phenyl)-2-methoxy-benzamide. The reaction mixture was then concentrated in vacuo and the residue was extracted into ethyl acetate. The ethyl acetate layer was washed with water and with cold aqueous hydrochloric acid, then dried over sodium sulphate and finally concentrated in vacuo. The residue obtained was chromatographed over silica gel to afford the desired product. 1H-NMR:delta6.95-8.01 (7H,aromatic), delta3.73(3H,OCH3) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | In tetrahydrofuran; methanol; | N-[2-(2,6-Dioxo-piperidin-3-yl)-1,3-dioxo-2,3-dihydro-1H-isoindol-4-yl]-2-methoxy-benzamide I-71 A mixture of 4-amino-2-(2,6-dioxo(3-piperidyl))isoindoline-1,3-dione (660 mg, 2.4 mmol) and 2-methoxybenzoyl chloride (0.7 mL, 4.7 mmol) in THF (20 mL) was heated to reflux for 15 h. To the mixture was added methanol (5 mL) to give a suspension. The suspension was filtered and washed with methanol (20 mL) to give N-[2-(2,6-dioxo-piperidin-3-yl)-1,3-dioxo-2,3-dihydro-1H-isoindol-4-yl]-2-methoxy-benzamide as a white solid (760 mg, 78% yield): mp, 286-287 C.; 1H NMR (DMSO-d6) (at 340K) delta2.09-2.14 (m, 1H, CHH), 2.55-2.66 (m, 2H, CH2), 2.85-2.98 (m, 1H, CHH), 4.14 (s, 3H, OCH3),5.19 (dd, J=5.5, 12.9 Hz, 1H, NCH), 7.17 (t, J=7.2 Hz, 1H, Ar), 7.30 (d, J=8.3 Hz, 1H, Ar), 7.61-7.68 (m, 2H, Ar), 7.89 (t, J=7.7 Hz, 1H, Ar), 8.12 (dd, J=1.8, 7.9 Hz, 1H Ar), 9.03 (d, J=8.5 Hz, 1H, Ar), 11.17 (s, 1H, NH), 11.64 (s, 1H, NH); 13C NMR (DMSO-d6) (at 340K) delta22.09, 31.02, 49.29, 56.19, 112.65, 116.31, 117.93, 120.66, 121.14, 125.52, 131.59, 131.75, 134.34, 136.22, 137.00, 157.64, 163.82, 166.69, 168.15, 169.43, 172.32; Anal Calcd for C21H17N3O6: C, 61.92; H, 4.21; N, 10.31. Found: C, 62.05; H, 4.10; N, 10.38. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | o-Anisoyl chloride (15.7 g, 92 mmol) was added dropwise to a solution ofaminobenzamide <strong>[63069-49-8]2-amino-5-fluorobenzamide</strong> (13.0 g, 84 mmol) and triethylamine (16 mL, 110 mmol) in tetrahydrofuran (100 mL) cooled in an ice bath. Immediately a precipitate started forming. Stirring of the solution was continued for 5 hours at room temperature. The formed precipitate was collected by filtration and was washed twice with diethyl ether and dried at 50 C in vacuo. The dried solid was suspended in 2 N aqueous sodium hydroxide solution (250 mL) and heated at reflux until a clear solution was obtained (3 hours). The reaction mixture was cooled to room temperature and filtered. The filtrate was acidified to pH<l with concentrated aqueous HC1. The formed precipitate was collected by filtration and washed twice with water,twice with methanol, and twice with diethyl ether. The solid was dried in an oven at 45 C to yield 6-fmoro-2-(2-methoxyphenyl)-3No.-quinazolin-4-one (18.2 g, 80%) as a white solid. | |
80% | 6-Fluoro-2-(2-methoxyphenyl)-3H-quinazolin-4-one o-Anisoyl chloride (15.7 g, 92 mmol) was added dropwise to a solution of <strong>[63069-49-8]2-amino-5-fluorobenzamide</strong> (13.0 g, 84 mmol) and triethylamine (16 mL, 110 mmol) in tetrahydrofuran (100 mL) cooled in an ice bath. Immediately a precipitate started forming. Stirring of the solution was continued for 5 hours at room temperature. The formed precipitate was collected by filtration and was washed twice with diethyl ether and dried at 50 C. in vacuo. The dried solid was suspended in 2 N aqueous sodium hydroxide solution (250 mL) and heated at reflux until a clear solution was obtained (3 hours). The reaction mixture was cooled to room temperature and filtered. The filtrate was acidified to pH<1 with concentrated aqueous HCl. The formed precipitate was collected by filtration and washed twice with water, twice with methanol, and twice with diethyl ether. The solid was dried in an oven at 45 C. to yield 6-fluoro-2-(2-methoxyphenyl)-3H-quinazolin-4-one (18.2 g, 80%) as a white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydrogencarbonate; In dichloromethane; water; | Example A.29a) Preparation of intermediate (65) 2-Methoxybenzoic acid (10.655 g, 0.0699 mol) was dissolved in DCM (100 ml). Thionyl chloride (10.09 ml, 0.1398 mol, 2 equivalents) and DMF (1 drop) were added and the mixture was refluxed for 2 hours. The solvent was evaporated and DCM(100 ml) was added again. The solvent was evaporated and again DCM (100 ml) was added. Then l-benzyl-4-(methylamino)piperidine (14.2 g, 0.0699 mol) and a saturated aqueous NaHCO3 solution (50 ml) were added. The two layer system was stirred and the layers were separated. The separated organic layer was dried (MgSOz}), filtered and the solvent was evaporated, yielding 22.83 g of intermediate (65). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In dichloromethane; | 2-Methoxy-benzoic acid (0.028 mol) was dissolved in DCM (150 ml). Thionyl chloride (8.2 ml) was added dropwise to this mixture and the mixture was refluxed for 2 hours and 30 minutes. The reaction mixture was cooled and the solvent was evaporated. Then DCM (150 ml) was added and the solvent was evaporated again. The crude compound was dissolved in DCM (150 ml). First l-(phenylmethyl)-3-pyrrolidinamine (0.028 mol) was added and then a saturated aqueous NaHCCb solution (75 ml) was added. The mixture was reacted for 2 hours. Then the layers were separated. The separated organic layer was dried (MgSO4), filtered and the solvent was evaporated. The residue was worked up in diisopropyl ether and the crude compound was purified by column chromatography (eluent : from 100 % CH2Cl2 till 3% CH3OH/CH2C12). The product fractions were collected and the solvent was evaporated, yielding 7.14 g of intermediate (21). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
25% | With magnesium ethylate; In tetrahydrofuran; at 0 - 20℃;Heating / reflux; | To a suspension of 14.34g of magnesium ethoxide (0.13 moles) in dry THF (100 ml.) was added 10.5g of ethyl hydrogenmalonate 1 5-2 (0.08 moles) and refluxed for 90 min. The reaction mixture was cooled to 0 C and a solution of 2-methoxybenzoyl chloride 5-3 (14.59g; 0.085 moles) in dry THF (25 ml.) was added at such a rate that the reaction temperature did not exceed 5 C. The reaction mixture was stirred at r.t for overnight and allowed to stand for two days. A saturated solution of ammonium chloride was added and the reaction mixture was extracted with EtOAc (3 x 50 ml_). The combined organic layer was washed with water and dried over anhydrous sodium sulphate. The solvent was evaporated to give the product as oil and was purified by column chromatography (hexane-EtOAc: 95:5) to yield the product (4.33g, 25% yield). The product was confirmed by spectral data. 1HNMR (CDCI3): 1.23 (3H, t), 3.85 (5H, s), 4.10- 4.22 (2H, q), 6.90-7.05 (2H, m), 7.42-7.51(1 H, m), 7.69-7.80 (1 H, d). |
25% | To a suspension of 14.34 g of magnesium ethoxide (0.13 moles) in dry THF (100 mL) was added 10.5 g of ethyl hydrogenmalonate 1 5-2 (0.08 moles) and refluxed for 90 min. The reaction mixture was cooled to 0 C. and a solution of 2-methoxybenzoyl chloride 2 (14.59 g; 0.085 moles) in dry THF (25 mL) was added at such a rate that the reaction temperature did not exceed 5 C. The reaction mixture was stirred at r.t for overnight and allowed to stand for two days. A saturated solution of ammonium chloride was added and the reaction mixture was extracted with EtOAc (3×50 mL). The combined organic layer was washed with water and dried over anhydrous sodium sulphate. The solvent was evaporated to give the product as oil and was purified by column chromatography (hexane-EtOAc: 95:5) to yield the product (4.33 g, 25% yield). The product was confirmed by spectral data. 1HNMR (CDCl3): 1.23 (3H, t), 3.85 (5H, s), 4.10-4.22 (2H, q), 6.90-7.05 (2H, m), 7.42-7.51 (1H, m), 7.69-7.80 (1H, d). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | The reactions were done as outlined in (K. O. [OLSEN,] J. Org. [CHEM.,] (1987) 52,4531-4536). Thus, to a stirred solution of lithium diisopropylamide in THF at-65 [TO-70] C was added freshly distilled ethyl acetate, dropwise. The resulting solution was stirred for 30 min and the acid chloride was added as a solution in THF. The reaction mixture was stirred at-65 to-70 [] C for 30 min and then terminated by the addition of 1 N HCI solution. The resulting two- phased mixture was allowed to warm to ambient temperature. The resulting mixture was diluted with EtOAc (100 mL) the organic layer was collected. The aqueous layer was extracted with EtOAc (100 mL). The organic layers were combined, washed with brine, dried [(NA2SO4),] and [CONCENTRATED IN VACUO] to give the crude [A-KEY] esters, which were used in the subsequent condensations. | |
99% | The reactions were done as outlined in (K. [O.] Olsen, J. Org. Chem. , (1987) 52,4531-4536). Thus, to a stirred solution of lithium diisopropylamide in THF at -65 TO-70C was added freshly distilled ethyl acetate, dropwise. The resulting solution was stirred for 30 min and the acid chloride was added as a solution in THF. The reaction mixture was stirred at-65 [TO-70C] for 30 min and then terminated by the addition of 1 N HCI solution. The resulting two-phased mixture was allowed to warm to ambient temperature. The resulting mixture was diluted with EtOAc (100 mL) the organic layer was collected. The aqueous layer was extracted with EtOAc (100 mL). The organic layers were combined, washed with brine, dried (Na2SO4), and concentrated in vacuo to give the crude (beta-keto esters, which were used in the subsequent condensations. | |
99% | The reactions were done as outlined in [(OLSEN,] K. O. J. Org. [CHEM.,] (1987) 52,4531-4536). Thus, to a stirred solution of lithium [DIISOPROPYLAMIDE] in THF at [- 65 TO-70C] was added freshly distilled ethyl acetate, dropwise. The resulting solution was stirred for 30 min and the acid chloride was added as a solution in THF. The reaction mixture was stirred at-65 [TO-70C] for 30 min and then terminated by the addition of 1 N HCI solution. The resulting two-phased mixture was allowed to warm to ambient temperature. The resulting mixture was diluted with EtOAc (100 mL) the organic layer was collected. The aqueous layer was extracted with EtOAc (100 mL). The organic layers were combined, washed with brine, dried [(NA2SO4),] and [CONCENTRATED IN VACUO] to give the crude [8-KETO] esters, which were used in the subsequent condensations By following essentially the same procedure set forth in Preparative Example 4 only substituting the acid chlorides shown in Column 2 of Table 3, the [ss-KETO] esters shown in Column 3 of Table 3 were prepared |
The reactions were done as outlined in (K. O. OLSEN, J. Org. CHEM., (1987) 52,4531-4536). Thus, to a stirred solution of lithium diisopropylamide in THF at-65 to-70 C was added freshly distilled ethyl acetate, dropwise. The resulting solution was stirred for 30 min and the acid chloride was added as a solution in THF. The reaction mixture was stirred at-65 to-70 C for 30 min and then terminated by the addition of 1 N HCI solution. The resulting two- phased mixture was allowed to warm to ambient temperature. The resulting mixture was diluted with EtOAc (100 mL) the organic layer was collected. The aqueous layer was extracted with EtOAc (100 mL). The organic layers were combined, washed with brine, dried (NA2S04), and concentrated in vacuo to give the crude P-KETO esters, which were used in the subsequent condensations. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With pyridine; at 20℃; for 2h;Inert atmosphere; | Galleacetophenone 3,4-dimethyl ether (1.00 g, 5.1 mmol, 1.0 equiv) was dissolved in 5 mL pyridine. To the solution was added 2-methoxybenzoyl chloride (1.14 mL, 7.65 mmol, 1.5 equiv). The solution was stirred for 2 h at room temperature, at which time the reaction was observed to be complete by TLC. The reaction was diluted with 15 mL 1N HCl and stirred for 10 min. The aqueous layer was extracted twice with 20 mL ethyl acetate, and the combined organic layers were washed three times with water and one time with brine. The organic layer was dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by flash column chromatography (hexanes/ethyl acetate) to afford 1.290 g of ester 6 (80% yield) as a white solid. 1H NMR (500 MHz, CDCl3) d: 8.12 (dd, 1 H, J = 1.8, 7.8 Hz), 7.67 (d, 1H, J = 8.9 Hz), 7.55 (m, 1 H), 7.06 (m, 2 H), 6.87 (d, 1 H, J = 8.9 Hz), 3.94(s, 3 H), 3.93 (s, 3 H), 3.84 (s, 3 H), 2.52 (s, 3 H). 13C NMR (125 MHz, CDCl3) d: 196.2,163.9, 160.0, 157.3, 144.7, 141.6, 134.4, 132.7, 125.9, 125.1, 120.4, 118.9,112.3, 109.2, 61.0, 56.2, 56.1, 30.0.HRMS: Expected ([M + H]+) 331.1183. Observed: 331.1176. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
47% | With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine; In N,N-dimethyl-formamide; at 50℃; for 25h; | <strong>[7418-65-7]4-aminonicotinic acid</strong> (0.100g, 0.724mmol) was dissolved in DMF (3.62mL), diisopropylethylamine (0.139mL, 0.796mmol) and 2-methoxybenzoyl chloride (0.113mL, 0.760mmol ) was added at room temperature. After stirring for 20 hours at the same temperature, HATU (0.302g, 0.796mmol) and Diisopropylethylamine (0.113mL, 0.760mmol) was added. After stirring at 50 for 5 hours, distilled water was added to the reaction mixture, and the mixture was extracted with diethyl ether. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane / ethyl acetate = 80 / 20-60 / 40) to give the title compound (0.0865g, 0.340mmol, 47%) as a pale yellow solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
0.83 g | With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 0 - 20℃;Inert atmosphere; | To a suspension of (4-bromo-2-methyl-phenyl)methanamine (1 .02 g, 5.10 mmol) and DIPEA (2.66 mL, 15.29 mmol) in anhydrous THF (20 mL), cooled at 0 °C under a nitrogen atmosphere, was added 2-methoxybenzoyl chloride (0.83 mL, 5.61 mmol). The reaction mixture was stirred overnight at room temperature, quenched with a saturated aqueous solution of ammonium chloride and then extracted with EtOAc (x3). The combined organics were washed with brine, dried over Na2S04 and filtered then concentrated under reduced pressure. Further purification by flash column chromatography on silica gel eluting with 0-30percent EtOAc in heptane gave /V-[(4-bromo-2-methyl- phenyl)methyl]-2-methoxy-benzamide (0.83 g, 2.49 mmol, 49percent yield) as a white solid. UPLC-MS (ES+, Short acidic): 1 .85 min, m/z 336.1 [M+2]+ |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
42% | With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 0 - 20℃; | To a solution of 1 -(4-bromophenyl)cyclopropanamine (534 mg, 2.52 mmol) and DIPEA (0.66 mL, 3.77 mmol) in anhydous THF (10 mL) was added 2-methoxybenzoyl chloride (0.41 mL, 2.77 mmol) at 0 C. The reaction mixture was then allowed to return to room temperature and stirred overnight. The mixture was quenched with a saturated solution of ammonimum chloride (20 mL), extracted with EtOAc (3 x 10 mL). The combined organic extracts were washed with water (2 x 10 mL), brine (10 mL), dried over sodium sulfate, filtered and concentrated under reduced pressure. Further purification by flash column chromatography (heptane/EtOAc 90:10 to 60:40) gave Lambda/-[1 -(4- bromophenyl)cyclopropyl]-2-methoxy-benzamide (362 mg,1 .05 mmol, 42% yield) as a white fluffy solid. UPLC-MS (ES+, Short acidic): 1 .98 min, m/z 346.1 [M]+ |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 0 - 20℃; | To a solution of 4-bromo-a-methylbenzylamine (1 .31 g, 6.57 mmol) and DIPEA (1 .72 mL, 9.85mmol) in anhydous THF (30 mL) was added 2-methoxybenzoyl chloride (1 .08 mL, 7.22 mmol) at 0 C. The reaction mixture was then allowed to return to room temperature and stirred overnight. The mixture was quenched with a saturated solution of ammonimum chloride (40 mL), extracted with EtOAc (3 chi 20 mL). The combined organic extracts were washed with water (2 chi 30 mL), brine (30 mL), dried over sodium sulfate, filtered and concentrated under reduced pressure. Further purification by flash column chromatography (heptane/EtOAc 90:10 to 60:40) gave /V-[1 -(4-bromophenyl)ethyl]-2- methoxy-benzamide (2.07 g, 6.19 mmol, 94% yield) as a white solid. UPLC-MS (ES+, Short acidic): 1 .96 min, m/z 336.1 [M+2]+ |
6.19 mmol | With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 0 - 20℃; for 15h; | A solution of 4-bromo-a-methylbenzylamine (6.57 mmol) and N,N-diisopropylethylamine (9.85 mmol) in anhydous THF (30 mL) and 2-methoxybenzoyl chloride (7.22 mmol) at 0 C was then allowed to return to RT and stirred for 15 h. The mixture was quenched with a saturated solution of ammonimum chloride (40 mL), extracted with EtOAc (3x20 mL). The combined organic extracts were washed with water (2x30 mL), a saturated solution of brine (30 mL), dried over sodium sulfate, filtered and concentrated under reduced pressure. Further purification gave the titled compound (6.19 mmol) as a white solid. UPLC-MS (ES, Short acidic): 1 .96 mi m/z 336.1 [M+2] |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
22% | A solution of freshly prepared potassium Jb/'s(trimethylsilyl)amide (4.92 g, 24.65 mmol) in dry THF (50 mL) was added dropwise to a solution of 2-(chloromethyl)-4,4,5,5-tetramethyl-1 ,3,2-dioxaborolane (4.35 g, 24.65 mmol) in dry THF (50 mL) cooled to -78 C. After stirring for 15 min at -78 C, the cooling bath was removed and the mixture was stirred for an additional 2 h at room temperature. Anhydrous MeOH (2 mL, 49.29 mmol) was then added at 0 C. After stirring for an additional 1 h at 0 C, 2-methoxybenzoyl chloride (7.3 mL, 49.29 mmol) was added. The reaction was warmed to room temperature and stirred for 24 h. The reaction mixture was concentrated under vacuum to remove THF then the resulting residue was diluted in anhydrous MeOH (50 mL) and cooled to 0 C before the addition of a saturated solution of potassium hydrogen fluoride (7.70 g, 98.59 mmol). The reaction mixture was warmed to room temperature and stirred for 30 min and then concentrated under vacuum. The residue was triturated with hot acetone (2 x 500 mL) and filtered. The filtrate was concentrated under vacuum until the appearance of the first crystals. Et20 (1500 mL) was then added. The precipitate was collected by filtration to give potassium trifluoro-[[(2- methoxybenzoyl)amino]methyl]boranuide (1 .48 g, 5.45 mmol, 22% yield) as a yellow solid. NMR (400 MHz, DMSO-cfe, delta): 10.34 (s, 1 H), 7.95 (dd, J = 8.0, 1 .8 Hz, 1 H), 7.74 (m, 1 H), 7.31 (d, J = 8.0 Hz, 1 H), 7.17 (m, 1 H), 3.98 (s, 3H), 2.46 (t, J = 9.9 Hz, 2H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
49% | Potassium bis(trimethylsilyl)amide in toluene (0.5 M, 23.8 mL, 11 .9 mmol) was added dropwise to a solution of 2-(bromomethyl)-4,4,5,5-tetramethyl-1 ,3,2-dioxaborolane (2.5 g, 11 .3 mmol) in dry THF (25 mL) at -78 C under nitrogen. After stirring for 25 mins at -78 C, the mixture was allowed to warm to RT and anhydrous methanol (1.3 mL, 32.1 mmol) was added. 2-Methoxybenzoyl chloride (3.4 mL, 22.6 mmol) was slowly added after 1 h and the mixture was stirred overnight. The resulting suspension was filtered and the filtrate concentrated under vacuum. The obtained residue was diluted in methanol (25 mL) followed by addition of an aqueous saturated solution of potassium hydrogen fluoride (3.5 g, 45.3 mmol). After stirring overnight, the mixture was concentrated under reduced pressure. The resulting residue was washed with hot acetone (x 4). The acetone phases were filtered and the filtrate was concentrated under reduced pressure until almost all acetone was gone. By subsequent addition of Et20, the product precipitated and was collected. Potassium trifluoro-[[(2- methoxybenzoyl)amino]methyl]boranuide (1 .50 g, 5.53 mmol, 49% yield) was obtained as white solid. UPLC-MS (ES+, Short acidic): 1.03 mi m/z 232.1 [M-K] |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
0.92 mmol | To a solution of <strong>[173999-23-0](5-bromo-2-pyridyl)methanamine</strong> (1 .60mmol) in DMF (4 mL), at 0 C, was added N,Ndiisopropylethylamine (4.81 mmol). After 10 mm of stirring, 2-methoxybenzoyl chloride (3.21 mmol) was added slowly. The reaction mixture was warmed to RT and stirred under nitrogen for 18 h. The mixture was quenched with saturated aqueous sodium bicarbonate solution and diluted with EtOAc. The layers were partitioned and the aqueous layer was extracted with EtOAc. The combined organic extracts were washed with brine, dried over sodium sulfate and concentrated under reduced pressure. Further purification gave the titled compound (0.92 mmol) as a pale yellow oil. UPLC-MS (ES, Short acidic): 1 .53 mi m/z 322.8 [M+2] |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
48.2% | A solution of o-anisoyl chloride (42.30 g, 0.248 mol) was dissolved in 1 ,2-Dichlorethane (100 mE) and added drop-wise to a nitrogen purged reaction vessel containing AlCl3 (33 g, 0.248 mol), 4,4?-sulfonylbis(phenoxy- benzene) 4,4?-sulfonylbis(phenoxybenzene) (5 g, 0.0161 mol) and CH2ClCH2Cl (100 mE). Upon complete addition, the reaction was allowed to stir at for 2 days at 25 C. Subsequently, H20 (100 mE) was added, then 1N HCl (100 mE, pH=0), and the mixture was then extracted with CH2Cl2 (3x200 mE). The combined organic layers were rotovapped to dryness to afford a dark solid that was stirred with 1N KOH (300 mE) and CH2C12 (200 mE) for 2 h at 25 C. to convert un-reacted carboxylates to water soluble sodium carboxlyate salts. This mixture was then extracted with CH2Cl2 (2x200 mE) and organic layers were combined, dried over anhydrous Mg504, filtered, and the solvent removed to afford a viscous, dark orange, oil comprised of a mixture of deprotected and methoxy protected 2-hydroxy- benzophenones as determined using TEC (5i02, eluant: 1:2 ethyl acetate/hexane). To convert the protected 4,4?-sulfo- nylbis2-methoxybenzophenone to the desired deprotected 4,4?-sulfonylbis2-hydroxybenzophenone, the product mixture was dissolved in toluene (125 mE), treated by the addition of solid A1Br3 (14.32 g, 0.0537 mol), and the resulting mixture was then heated to reflux for 1 h, cooled to room temperature, and stirred at 25 C. overnight. Subsequently, the reaction mixture was treated with 1 M HCl (375 mE) to neutralize any residual A1Br3 and was then stirred for 1 hat 25 C. at which point the aqueous layer was extracted with toluene (3x100 mE) and separated. The combined organic layers were then dried over anhydrous Mg504, filtered, and the solvent removed in vacuo to afford a dark viscous oil. Purification via colunm chromatography (5i02, eluant: 1:3 ethyl acetate/hexane gradient with 1:2 ethyl acetate/hexane, R1=0.48), afforded pure (((sulfonylbis (4,1 -phenylenebis(oxybis(4, 1 -phenylenebis((2-hy- droxyphenyl)methanone) as a pale yellow solid (3.7 g, 48.2%). ?H NMR (DMSO-d6): 6=10.34 (s, 2H, OH), 8.00 (m, 4H, SO2CCHAr), 7.79 (m, 4H, OrrrCCCHAr), 7.43 (m, 2H, CHAT), 7.34 (m, 2H, CHAT), 7.28-7.22 (m, 8H, CHAT), 6 .99-6 .92 (m, 4H, CHAr). HRMS (ASAP with APCI): mlz642.1192 (M+., calculated for C38H26085 642.1348). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With aluminum (III) chloride; In 1,2-dichloro-ethane; at 25℃; for 48.0h;Inert atmosphere; | A solution of o-anisoyl chloride (42.30 g, 0.248 mol) was dissolved in 1 ,2-Dichlorethane (100 mE) and added drop-wise to a nitrogen purged reaction vessel containing AlCl3 (33 g, 0.248 mol), 4,4?-sulfonylbis(phenoxy- benzene) 4,4?-sulfonylbis(phenoxybenzene) (5 g, 0.0161 mol) and CH2ClCH2Cl (100 mE). Upon complete addition, the reaction was allowed to stir at for 2 days at 25 C. Subsequently, H20 (100 mE) was added, then 1N HCl (100 mE, pH=0), and the mixture was then extracted with CH2Cl2 (3x200 mE). The combined organic layers were rotovapped to dryness to afford a dark solid that was stirred with iN KOH (300 mE) and CH2Cl2 (200 mE) for 2 h at 25 C. to convert un-reacted carboxylates to water soluble sodium carboxlyate salts. This mixture was then extracted with CH2Cl2 (2x200 mE) and organic layers were combined, dried over anhydrous Mg504, filtered, and the solvent removed to afford a viscous, dark orange, oil comprised of a mixture of deprotected and methoxy protected 2-hydroxy- benzophenones as determined using TEC (5i02, eluant: 1:2 ethyl acetate/hexane). To convert the protected 4,4?-sulfo- nylbis2-methoxybenzophenone to the desired deprotected 4,4?-sulfonylbis2-hydroxybenzophenone, the product mixture was dissolved in toluene (125 mE), treated by the addition of solid AlBr3 (14.32 g, 0.0537 mol), and the resulting mixture was then heated to reflux for 1 h, cooled to room temperature, and stirred at 25 C. overnight. Subsequently, the reaction mixture was treated with 1 M HCl (375 mE) to neutralize any residual A1Br3 and was then stirred for 1 hat 25 C. at which point the aqueous layer was extracted with toluene (3x100 mE) and separated. The combined organic layers were then dried over anhydrous Mg504, filtered, and the solvent removed in vacuo to afford a dark viscous oil. Purification via colunm chromatography (5i02, eluant: 1:3 ethyl acetate/hexane gradient with 1:2 ethyl acetate/hexane, R1=0.48), afforded pure (((sulfonylbis (4,1 -phenylenebis(oxybis(4, 1 -phenylenebis((2-hy- droxyphenyl)methanone) as a pale yellow solid (3.7 g, 48.2%). ?H NMR (DMSO-d6): 6=10.34 (s, 2H, OH), 8.00 (m, 4H, SO2CCHAr), 7.79 (m, 4H, OrrrCCCHAr), 7.43 (m, 2H, CHAT), 7.34 (m, 2H, CHAT), 7.28-7.22 (m, 8H, CHAT), 6 .99-6 .92 (m, 4H, CHAr). HRMS (ASAP with APCI): mlz642.1192 (M+., calculated for C38H26085 642.1348). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
General procedure: Pyridine (4 mL) was added to 2- methoxybenzoylmethylammonium chloride (8a)/benzoylmethylammonium chloride (8b) salt (0.5 mmol) and stirred for 10 min at room temperature. To this mixture, above corresponding acid chloride was added slowly and stirred for 1 h under nitrogen atmosphere. After completion of the reaction, water (4 mL) was added, neutralized with 3 N HCl, and extracted with EtOAc (2 × 20 mL). The combined organic layer was washed with water (2 × 15 mL), brine (15 mL), dried over anhydrous Na2SO4, and concentrated in vacuo. To this crude, acetic anhydride (3 mL) followed by conc. H2SO4 (0.1 mL) were added at room temperature and the mixture was stirred at 90C for 1 h. After completion of the reaction, cooled to room temperature, H2O (5 mL) was added. The mixture was neutralized with saturated aqueous NaHCO3 and extracted with EtOAc (2 × 25 mL). The combined organic layer was washed with water (2 × 15 mL), brine (15 mL), dried over anhydrous Na2SO4, and concentrated in vacuo. The crude was purified by column chromatography (EtOAc:hexane = 1:3) to afford the pure oxazole product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | 300 mg (0.581 mmol) of <strong>[3482-49-3]fusidic acid</strong> and 142 mg (1.161 mmol) of 4-dimethylaminopyridine (DMAP) were first weighed in a 50 mL magnetron-containing round bottom flask,Under nitrogen protection, measure 10 mL of ultra-dried anhydrous methylene chloride in a flask, and stir at room temperature under nitrogen for about 15 minutes until it is completely dissolved.0.94 mL (1.161 mmol) of pyridine was added via syringe, stirred under nitrogen at room temperature for about 20 min, and finally 0.36 mL (1.743 mmol) of o-methoxybenzoyl chloride was added three times and stirred under nitrogen at room temperature. Reaction 2h.The end point of the reaction was checked by TLC (developer: dichloromethane:ethyl acetate=3:1, coloring agent: methanol: acetic acid: concentrated sulfuric acid: anisaldehyde (volume ratio)=85:10:5:0.5), and the reaction was completed. The crude product of compound FA-E-11 was obtained by washing and extractive drying and the like, and purified by silica gel column chromatography (eluent: dichloromethane:ethyl acetate=6:1) to give compound FA-E-11, which The molecular structural formula is shown in FIG. 11 , white solid, Rf=0.40 (developer: dichloromethane:ethyl acetate=3:1), yield: 71%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With pyridine; at -40℃; | General procedure: Using a typical scale of 1.0 mmol, 1 (1.0 mmol) was dissolved inanhydrous pyridine (2 mL) in a small round-bottomed flask and themixture was cooled to 40 C after which the acid chloride(2.0 mmol; purchased or prepared as above) in dry THF or DMF(2 mL) was added dropwise over 20 min with vigorous stirring.After 2-6 h the reaction mixturewaswarmed to room temperatureand the solvent reduced under pressure. Without using a work-upthe crude product was purified by column chromatography directlyusing MeOH/DCM mixtures (1:99 to 2:8). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | General procedure: Method B is a modification of Method A and was performed under nitrogen atmosphere andwith extended work-up. Substituted benzoyl chloride (1.5 mmol, 1.2 equiv) was placed into the askunder nitrogen, diluted with dry DCM (5 mL) and dry pyridine (400 mg, 5 mmol, 4 equiv) was added.The mixture was mixed for 5 min under nitrogen. Then, <strong>[33332-29-5]5-chloropyrazin-2-amine</strong> (162 mg, 1.25 mmol,1 equiv) dissolved in DCM (10 mL) was added dropwise over 10 min under nitrogen ow. The askwas closed by septum and stirred for additional 6 h. After reaction, the mixture was diluted with DCMto the final volume of 40 mL and washed with water (1 30 mL), 5% (m/m) aqueous NaHCO3 solution(1 30 mL), and brine (1 30 mL). The organic layer was dried over anhydrous Na2SO4 and adsorbedon silica (4 g) by evaporating the solvents under reduced pressure. Automated flash chromatographywas run using same conditions as described in Method A. If needed, the products were recrystallizedfrom hot EtOH (crystallization initiated by cooling and dropwise addition of cold water). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
20% | General procedure: A mixture of dry dichloromethane (DCM, 2 mL) and dry pyridine (475 mg, 6 mmol, 3 molarequiv) was put into 25 mL round-bottom flask, closed with a stopper and cooled in a freezer forapproximately 15 min. A selected benzoyl chloride (2.4 mmol, 1.2 equiv) was diluted with dry DCM(5 mL) and added dropwise to the cooled (ice bath) pyridine/DCM mixture under stirring, and the mixture was stirred for additional 5 min in the closed flask. 2-Aminopyrazine (190 mg, 2 mmol,1 equiv) or 6-chloropyrazin-2-amine (259 mg, 2 mmol, 1 equiv) was dissolved in DCM (2 mL) andadded dropwise to the cooled reaction mixture over 10 min upon stirring. After additional 15 min,the reaction was removed from the ice bath and stirred at laboratory temperature. The progress ofreaction was monitored by TLC (silica plates, 33percent EtOAc in hexane). After 2 h, no significant furtherincrease in the spot of the product was observed, so the reaction was ended and worked-up.The reaction mixture was adsorbed on silica (4 g) by evaporating the solvents underreduced pressure. The mixture on silica was used for solid loading the flash chromatographypre-column. The separation used the following conditions: manually filled silica column (30 g),continuous gradient elution 0?50percent EtOAc in hexane, flow rate 35 mL/min, detection wavelength280 nm, monitoring wavelength 260 nm. Fractions containing pure product were combined andsolvents were evaporated under reduced pressure to yield solid product. If needed, the productswere recrystallized from hot EtOH, the crystallization was induced by cooling and addition of water.The products were isolated as white solids. In several cases, the final products were still contaminatedwith non-specified impurity of brown color. This impurity was easily removed by dispersing theproduct in small amount of hexane and immersion of a vertical piece of filtration paper into thisdispersion. The impurity was soluble in hexane and rose by capillary action to the filtration paper. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
64.8% | In tetrahydrofuran; at 20℃; for 3h; | 41.0 g (133.54 mol) of Intermediate 14, 22.7 g (133.54 mol) of 2-methoxybenzoyl chloride and 500 mL of THF were added and the mixture was stirred at room temperature for 3 hours. After the reaction was completed, the solvent was distilled off under reduced pressure. And solidified with diisopropyl ether (IPE) to obtain 38.2 g (yield: 64.8%) of a white solid compound (Intermediate (15)). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89.3% | In tetrahydrofuran; at 20℃; for 3h; | 45.0 g (197.26 mol) of Intermediate 21, 33.7 g (197.26 mol) of 2-methoxybenzoyl chloride and 650 mL of THF were added and the mixture was stirred at room temperature for 3 hours. After the reaction was completed, the solvent was distilled off under reduced pressure. And solidified with diisopropyl ether (IPE) to obtain 63.8 g (yield: 89.3%) of a white solid compound (intermediate (22)). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | With triethylamine; In dichloromethane; at 20℃; for 2h;Inert atmosphere; | General procedure: To a solution of 1,12-<strong>[2783-17-7]diaminododecane</strong> (26 mmol, 1 eq) in 80 ml of anhydrous methylene chloride under nitrogenatmosphere are added simultaneously via syringes, triethylamine (130 mmol, 5 eq) andbenzoyl chloride (78.3 mmol, 3 eq) dissolved in 50 mL of anhydrous methylene chloride.After 2 hours at room temperature, filtration of the white solide and washed with water anddiethyl ether gave the desired dibenzamide 3a-g. |
Tags: 21615-34-9 synthesis path| 21615-34-9 SDS| 21615-34-9 COA| 21615-34-9 purity| 21615-34-9 application| 21615-34-9 NMR| 21615-34-9 COA| 21615-34-9 structure
[ 1261782-53-9 ]
4-Hydroxy-2-methoxybenzoyl chloride
Similarity: 0.98
[ 1245531-38-7 ]
2-Methoxy-4,5-dimethylbenzoyl chloride
Similarity: 0.93
[ 1261782-53-9 ]
4-Hydroxy-2-methoxybenzoyl chloride
Similarity: 0.98
[ 1245531-38-7 ]
2-Methoxy-4,5-dimethylbenzoyl chloride
Similarity: 0.93
[ 1261782-53-9 ]
4-Hydroxy-2-methoxybenzoyl chloride
Similarity: 0.98
[ 1245531-38-7 ]
2-Methoxy-4,5-dimethylbenzoyl chloride
Similarity: 0.93
[ 1261782-53-9 ]
4-Hydroxy-2-methoxybenzoyl chloride
Similarity: 0.98
[ 1245531-38-7 ]
2-Methoxy-4,5-dimethylbenzoyl chloride
Similarity: 0.93
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H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
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