* 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.
Method 2 A suspension of 3-[1-methanesulfonylpropyl)-3-indolyl]-4-(3-indolyl)-1H-pyrrole-2,5-dione (70.39 g, 0.152 mole) in THF (1015 mL) was treated with a 40% aqueous solution of dimethylamine (423 mL, 3.37 moles) and the solids dissolved immediately to give a solution which was stirred at room temperature for 16 hrs. The reaction was worked up extractively with CH2 Cl2 (1500 mL) and water (2* 1000 mL) and the solvent was removed in vacuo to give 59.98 g (96%) of the-titled compound. NMR. MS (FD) m/z=412 (M+, 100%). Analytical calculated for C25 H24 N4 O2 C, 72.80; H, 5.87; N, 13.58. Found C, 71.80; H, 6.31; N, 12.93.
59.98 g (96%)
Example 7 3-[1-(3-Dimethylaminopropyl)-3-indolyl]-4-(3-indolyl)-1 H -pyrrole-2,5-dione Method 1 : A suspension of 1-(Dimethylaminopropyl)-indole-3-acetamide (0.60 g, 2.31 mmol) and methyl indolyl-3-glyoxylate (0.94 g, 4.63 mmol) in THF (10 mL) was cooled in an ice bath under N2and then treated with a 1 molar solution of potassium tert-butoxide in THF (9.3 mL, 9.30 mmol). The resultant dark reaction mixture was stirred 5 minutes in the ice bath and 3 hrs. at room temperature. The reaction was worked up extractively using EtOAc (100 mL), water (2X 75 mL), brine (25 ml) and the organic layer dried (MgSO4) and the solvent removed in vacuoto give a 1.13 g of a foam. Acetone (8 mL) was added to dissolve the foam and the product crystallized out and was isolated by filtration to give 0.80 g (84%) of the titled compound after drying. Method 2 : A suspension of 3-[1-methanesulfonylpropyl)-3-indolyl]-4-(3-indolyl)-1H-pyrrole-2,5-dione (70.39 g, 0.152 mole) in THF (1015 mL) was treated with a 40% aqueous solution of dimethylamine (423 mL, 3.37 moles) and the solids dissolved immediately to give a solution which was stirred at room temperature for 16 hrs. The reaction was worked up extractively with CH2Cl2(1500 mL) and water (2X 1000 mL) and the solvent was removed in vacuoto give 59.98 g (96%) of the titled compound. NMR. MS (FD) m/z= 412 (M+, 100%). Analytical calculated for C25H24N4O2C, 72.80; H, 5.87; N, 13.58. Found C, 71.80; H, 6.31; N, 12.93.
15
[ 776262-13-6 ]
[ 133053-48-2 ]
2-(1H-indol-3-yl)-3-[1-(3-dimethylaminopropyl)-1H-indol-3-yl]-maleic acid anhydride hydrochloride[ No CAS ]
[ 119139-20-7 ]
[ 109-54-6 ]
[ 133052-90-1 ]
Yield
Reaction Conditions
Operation in experiment
With ammonium acetate; potassium hydroxide; sodium hydrogencarbonate; potassium carbonate; In methanol; ethanol; water; acetone; toluene;
EXAMPLE 2 2-(1H-Indol-3-yl)-3-[1-(3-dimethylaminopropyl)-1H-indol-3-yl]-maleinimide 0.20 g (0,44 mmol) 2-(1H-indol-3-yl)-3-[1-(3-dimethylaminopropyl)-1H-indol-3-yl]-maleic acid anhydride hydrochloride and 10 g ammonium acetate are heated to 140 C. for 30 minutes. After cooling, the reaction mixture is mixed with water and extracted with ethyl acetate. The organic phase is well washed out with an aqueous solution of sodium bicarbonate and thereafter with water and dried over anhydrous sodium sulphate. The ethyl acetate is removed by rotary evaporation, the red residue obtained is stirred with a little water and the precipitated red product is filtered off with suction. After drying in a vacuum at 0.1 Torr and 140 C., there is obtained 0.156 g (91% of theory) of red product; m.p. about 280 C. (decomp.); RF=0.16 (chloroform/methanol 10:2 v.v). The 2-(1H-indol-3-yl)-3-[1-(3-dimethylaminopropyl)-1H-indol-3-yl]-maleic acid anhydride used as starting material is prepared as follows: 0.5 g (0.95 mmol) 2-(1-tert.-butoxycarbonyl-1H-indol-3-yl)-3-[1-(3-dimethylaminopropyl)-1H-indol-3-yl)-N-methylmaleinimide and 50 ml of a 10% solution of potassium hydroxide in methanol/water (1:1 v/v) are heated under reflux for 30 minutes. After cooling, the reaction mixture is carefully acidified with concentrated hydrochloric acid and extracted with chloroform. The organic phase is washed out with water and evaporated to dryness. The red residue is triturated with a little methanol/toluene, filtered off with suction and dried at 80 C. There are obtained 0.34 g (79.5% of theory) of a dark red product; m.p. 232-234 C. (decomp.). The 2-(1-tert. -butoxycarbonyl-1H-indol-3-yl)-3-[1-(3-dimethylaminopropyl)-1H-indol-3-yl]-N-methylmaleinimide used as starting material is prepared as follows: A mixture of 0.9 g (2.03 mmol) 2-(1-tert.-butoxycarbonyl-1H-indol-3-yl)-3-(1H-indol-3-yl)-N-methylmaleinimide (Tetrahedron, 44, 2887/1988), 0,3 g potassium carbonate and 0.3 g (2.4 mmol) 3-dimethylaminopropyl chloride in 10 ml acetone is stirred for 12 hours at ambient temperature and for 8 hours under reflux. After cooling, the reaction mixture is poured into water and extracted with ethyl acetate. The red extract is evaporated and the residue flash chromatographed on silica gel (Merck Type 7734) using, as elution agent, a mixture of toluene/ethanol (10+1.5 v/v). The desired product is obtained in the form of a red oil and used as such in the above reaction. Yield 0.8 g (74% of theory); RF=0,20 (toluene/ethanol 1:2 v/v).
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