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CAS No. : | 2620-50-0 | MDL No. : | MFCD00005840 |
Formula : | C8H9NO2 | Boiling Point : | No data available |
Linear Structure Formula : | - | InChI Key : | ZILSBZLQGRBMOR-UHFFFAOYSA-N |
M.W : | 151.16 | Pubchem ID : | 75799 |
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 |
---|---|---|
With triethylamine; | Example 65 4-(3,4-Methylenedioxybenzyl)amino-6-cyanoquinazoline STR126 15 ml of isopropyl alcohol, 75 mg of triethylamine and 125 mg of piperonylamine were added to 140 mg of <strong>[150449-97-1]4-chloro-6-cyanoquinazoline</strong>. The obtained mixture was heated under reflux for 5 hours and filtered to recover a precipitate. This precipitate was introduced to a silica gel column, followed by eluding with ethyl acetate to give 200 mg of the title compound. molecular formula; C17 H12 N4 O2 yield (%); 89 m.p. (C.); 243~244 Mass; 305 (M+1)+ NMR delta (DMSO-d6); 4.67 (2H, d, J=5.6Hz), 5.96 (2H, s), 6.84 (2H, s), 6.95 (1H, s), 7.77 (1H, d, J=8.4Hz), 8.56 (1H, s), 8.89 (1H, s), 9.04 (1H, br) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine; In dichloromethane; | EXAMPLE 1 3.02 g of 3,4-methylenedioxybenzylamine ("A") are added to a solution of 3.29 g of <strong>[76872-23-6]2,4-dichloro-6-methylthieno[2,3-d]pyrimidine</strong> in 80 ml of dichloro-methane, and, after 1.52 g of triethylamine have been added, the mixture is stirred for 12 hours at room temperature. The solvent is removed and worked up as customary. This gives 3.38 g of 2-chloro-6-methyl-4-(3,4-methylenedioxybenzylamino)thieno[2,3-d]pyrimidine, m.p. 162. | |
With triethylamine; In dichloromethane; | EXAMPLE 1 3.02 g of 3,4-methylenedioxybenzylamine ("A") are added to a solution of 3.29 g of 2,4-dichloro-6-methylthieno-[2,3-d]-pyrimidine in 80 ml of methylene chloride and, after addition of 1.52 g of triethylamine, the mixture is stirred at room temperature for 12 hours. The solvent is removed and the residue is worked up in the customary manner. 3.38 g of 2-chloro-6-methyl-4-(3,4-methylenedioxybenzylamino)-thieno-[2,3-d]-pyrimidine are obtained, m.p. 162. | |
With triethylamine; In dichloromethane; | EXAMPLE 1 2-Chloro-6-Methyl-4-(3,4-Methylenedioxybenzylamino)-Thieno-[2,3-d]-Pyrimidine A solution of 2,4-dichloro-6-methyl-thieno-[2,3-d]-pyrimidine (3.29 g) in dichloromethane (30 ml) is charged with 3,4-methylenedioxybenzylamine ("A") (3.02 g). Triethylamine (1.52 g) is added, and the mixture is stirred at room temperature. The solvent is removed, and the usual workup yields 2-chloro-6-methyl-4-(3,4-methylenedioxybenzylamino)-thieno-[2,3-d]-pyrimidine (3.38 g) Mp. 162 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
EXAMPLE 2 2-Chloro-5-Methyl-4-(3,4-Methylenedioxybenzylamino)-Thieno-[2,3-d]-Pyrimidine Following the procedure of Example 1, the reaction of 3,4-methylenedioxybenzylamine with <strong>[56844-38-3]2,4-dichloro-5-methyl-thieno-[2,3-d]-pyrimidine</strong> gives 2-chloro-5-methyl-4-(3,4-methylenedioxybenzylamino)-thieno-[2,3-d]-pyrimidine |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine; | EXAMPLE 65 4-(3,4-Methylenedioxylbenzyl)amino-6-cyanoquinazoline STR99 15 ml of isopropyl alcohol, 75 mg of triethylamine and 125 mg of piperonylamine were added to 140 mg of <strong>[150449-97-1]4-chloro-6-cyanoquinazoline</strong>. The obtained mixture was heated under reflux for 5 hours and filtered to recover a precipitate. This precipitate was introduced to a silica gel column, followed by eluding with ethyl acetate to give 200 mg of the title compound. molecular formula; C17 H12 N4 O2; yield(%); 89; m.p.( C.); 243~244; Mass; 305 (M+1)+; NMR delta (DMSO-d6); 4.67 (2H, d, J=5.6 Hz), 5.96 (2H, s), 6.84 (2H, s), 6.95 (1H, s), 7.77 (1H, d, J=8.4 Hz), 8.56 (1H, s), 8.89 (1H, s), 9.04 (1H, br). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | To a solution of 3, [4-METHYLENEDIOXYDIHYDROCINNAMIC] acid (0.4 g) in dry [CH2CK] (25 [ML)] under nitrogen, was added oxalyl chloride (0.5 [ML)] with three drops of dry DMF and the mixture was stirred for 1 hour. Solvents were removed in vacuo giving the acid chloride as a yellow solid. To a solution of the acid chloride in dry [CH2CL2] (50 [ML)] under nitrogen, cooled to [0C,] was added dropwise, a solution of 3, 4-(methylenedioxy)benzylamine (0.35 [G)] and pyridine (0.2 [ML)] in [CH2C12] (5 ml). The reaction mixture was stirred for 30 minutes at room temperature, diluted with [CHUCK] (100 [ML),] washed with aqueous HCl (100 [ML] ; [10%)] and sodium bicarbonate solution (100 [ML)] then dried and evaporated in vacuo to give DC-0058B as an off white powder (0.536g, 80%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
A library of compounds in which R4 was various groups having the formula [CONHR ?] was prepared by the process described above using 4-fluoro-3-nitrobenzoic acid, as follows: [72] Aldehyde resin was mixed with a primary amine (R17-NH2) in [DICHLOROETHANE] (DCE), triethylorthoformate (TEOF), and DMF (containing [1%] acetic acid) in a 1: 1: 1 ratio. After shaken overnight, sodium triacetoxyborohydride (20 eq. ) dissolved in DMF was added (Abdel-Magid, A. F. , et al., Tetrahedron Lett, 3 1: 5595-5598 (1990) ). After the mixture was shaken at room temperature overnight, the resin was filtered and washed with DMF (3 x 5 mL), [MEOH] [(3 X 5] mL), DMF [(3 X 5] mL), [MEOH] [(3 X 5] mL), and [CH2CL2] [(3 X 5] mL). The resin was washed twice with 5 mL DMF containing [1%] Hunig's base. To the filtered resin was added a mixture of 4-fluoro-3-nitrobenzoic acid (FNBA, 10 eq. ) and diisopropylcarbodiimide (DIC, 5 eq. ) in 2: 1 DMF : DCM. After shaking at room temperature overnight, the resin was filtered and washed with DMF (3 x 5 mL) and [CH2C12] (3 x 5 mL). [73] The resin was shaken with a primary amine [(R2-NH2)] in DMF for 8 hrs, filtered, and washed with DMF (6 x 5 mL), [MEOH] [(3 X 5] mL), and CH2C12 (3 x 5 mL). The aryl nitro group was reduced by the addition of tin (II) chloride dihydrate (20 eq. , >2 M) and N-methyl morpholine (NMM, 20 eq. ) in N-methyl pyrrolidinone (NMP). After shaken at room temperature overnight, the resin was filtered and washed with NMP (3 x 5 mL), [MEOH] (3 x 5 mL), and [CH2CI2 (3 X 5] mL). The resulting resin was shaken at room temperature with cyanogen bromide (5 eq. ) overnight, filtered, and washed with CH2Cl2 (3 x 5 mL), [MEOH] (3 x 5 mL), and CH2CI2 (3 x 5 mL). To produce a free amine, the resin was shaken for 30 min. in CHCl2 with the addition of sodium methoxide in methanol, filtered, and washed with CH2Cl2 [(4 X 5] mL). [[74]] In the final diversification step, the resin was heated at 500 C in DMF with a mono- substituted epoxide [[RLCH (-CH2O-)].] After shaking for 2 to 4 days the resin was filtered and washed with DMF (5 x 5 mL), [MEOH] [(3 X 5] mL), and CH2Cl2 (3 x 5 mL). T he resin-bound benzimidazole was cleaved from the solid-support by treatment with TFA: [CH2C12] (2: 3) for 1 hour at room temperature. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
45% | General procedure: To solutions of the corresponding 2-phenoxyalkylcarboxylicacids in DMF (5 mL/mmol) were added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDCI; 1.1 equiv) and 1-hydroxy-7-azabenzotriazole (1.1 equiv). The solutions were stirredat room temperature for 30 min, then the corresponding benzylamines(1.2 equiv) and diisopropylethylamine (3.0 equiv) wereadded. The resulting mixtures were stirred at room temperaturefor an additional 16 h, then poured into 10% aqueous citric acidsolutions. The aqueous mixtures were extracted with EtOAc, andthe extracts were washed with 5% aqueous NaHCO3 and brine, thendried over MgSO4, filtered, and evaporated to provide white solids.The solids were crystallized from EtOAc/hexane to provide theproducts 1, 2, and 6a. | |
45% | To a solution of (i?)-2-(2,4-dichlorophenoxy)propionic acid (compound 10a; 128 mg, 0.55 mmol), l-hydroxy-7-azabenzotriazole (82 mg, 0.60 mmol, 1.1 eq), and JV-(3- dimethylaminopropyl)-Lambda/"-ethylcarbodiimide hydrochloride (115 mg, 0.60 mmol, 1.1 eq) in dry DMF (3 mL) was added piperonylamine (0.81 mL, 0.65 mmol, 1.2 eq). The solution was stirred at room temperature for 30 minutes. Diisopropylethylamine (0.28 mL, 1.7 mmol, 3.0 eq) was then added, and the solution was stirred at room temperature for 16 hours. The reaction was poured into 10% aqueous citric acid (20 mL) and extracted with EtOAc (30 mL x 3). The combined organic extracts were dried over Na2SO4, and evaporated to provide a residue which was subjected to chromatography on silica gel with 20% EtOAc/hexane. The fractions were pooled and evaporated to yield 91 mg (45%) of compound 11a (designated MBX 1684) as a white solid: Rf 0.52 (50% EtOAc-Hexanes); mp 136-138 C; MS (ESI) m/z 368.0 [M+H]+; 1H NMR (CDCl3) delta 7.37 (d, IH), 7.19 (dd, IH), 6.91 (s, IH), 6.85 (d, IH), 6.76-6.68 (m, 3H), 5.95 (s, 2H), 4.73 (q, IH), 4.39 (m, 2H), 1.64 (d, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80.3% | In ethyl acetate; at 20℃; | 4-Chloroisobenzofuran-1,3-dione (230 mg, 1.25 mmol) dissolved in 5 mL of ethyl acetate and stirred at room temperatureSolution, drop into piperine (188mg, 1.25mmol), will immediately produce a large amount of white solids, TLC monitoring, after the reaction is completed, staticThe mixture was filtered and dried to give Compound 4 in a yield: 80.3%. |