Use of indole compounds in the preparation of medicines
A compound, indole technology, applied in the field of medicine
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Embodiment 1
[0075] Example 1: Preparation of 3-[(1-methyl-1H-indole-2-carbonyl)amino]propionic acid (compound 1-1)
[0076]
[0077] Step 1: Preparation of ethyl 3-[(1-methyl-1H-indole-2-carbonyl)amino]propionate (intermediate B-1)
[0078] Compound A-1,1-methylindole-2-carboxylic acid (3.61 g, 20.62 mmol) was dissolved in 15 mL of anhydrous CH 2 Cl 2 In, 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI, 4.35 g, 22.69 mmol) was dissolved in 10 mL of anhydrous CH 2 Cl 2 In, β-alanine ethyl ester hydrochloride (3.49 g, 22.72 mmol) and 4-dimethylaminopyridine (DMAP, 4.26 g, 34.86 mmol) were dissolved in 20 mL of anhydrous CH 2 Cl 2 , then the above three solutions were mixed, stirred in an ice bath for 4 h, and then placed at room temperature to react, and TLC monitored that the reaction was complete. 10mL CH 2 Cl 2 Extract three times, collect the lower layer solution through anhydrous Na 2 SO 4 It was dried overnight, filtered, concentrated under reduced pressu...
Embodiment 2
[0083] Example 2: Preparation of N-(1H-indole-2-carbonyl)-glycine methyl ester (compound 2-1)
[0084]
[0085] Step 1: Preparation of N-(3-(2-nitrophenyl)-pyruvyl)-glycine methyl ester (intermediate E-1)
[0086] Compound D-1 (0.44 g, 1.20 mmol) was dissolved in 10 mL of methanol solution containing 10% (volume ratio) concentrated hydrochloric acid, stirred and refluxed for 2.5 h, and the reaction was monitored by TLC. After cooling to room temperature, the solution was filtered and the solvent was evaporated. A quantitative amount of ethyl acetate was added to the residue and washed with brine, washed over anhydrous Na 2 SO 4 It was dried, filtered and concentrated, and purified by silica gel column chromatography [eluent: V (hexane): V (ethyl acetate) = 3: 2] to obtain intermediate E-1 as a yellow solid (0.26 g).
[0087] Step 2: Preparation of N-(1H-indole-2-carbonyl)-glycine methyl ester (compound 2-1)
[0088] Compound E-1 (0.26 g, 10 mmol) was dissolved in 10 mL ...
Embodiment 3
[0090] Example 3: Preparation of N-(1H-6-aminoindole-2-carbonyl) glycine methyl ester (compound 2-2)
[0091]
[0092] Step 1: Preparation of N-(3-(2,4-dinitrophenyl)pyruvyl)glycine methyl ester (intermediate E-2)
[0093] Compound D-2 (1.341 g, 3.0 mmol) was dissolved in 1 mL of methanol solution containing 10% (volume ratio) concentrated hydrochloric acid, sealed, stirred at 130° C. for 5 minutes, and monitored by TLC. After cooling to room temperature, the solution was filtered and the solvent was evaporated in vacuo. Add 50 mL of ethyl acetate to the residue, wash with 50 mL of brine, wash over anhydrous Na 2 SO 4 It was dried, filtered and concentrated, and purified by silica gel column chromatography [eluent: V (hexane): V (ethyl acetate) = 3: 2] to obtain compound E-2 (1.0179 g) as a yellow solid.
[0094] Step 2: Preparation of N-(1H-6-aminoindole-2-carbonyl)glycine methyl ester (compound 2-2)
[0095] Compound E-2 (0.906 g, 10 mmol) was dissolved in 20 mL of ethy...
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