Propionic Acid → HCID 15291423, compound

Into 2 ml of DMF were dissolved 200 mg (0.68 mmol) of cis-3-amino-4-methyl-1-(l-methylindazol-3-ylcarbonyl)pyrrolidine hydrochloride and 0.09 ml (0.68 mmol) of triethylamine, and the solution was stirred for 0.5 hours at room temperature. This solution was added to another solution which was separately prepared by dissolving 0.05 ml (0.68 mmol) of propionic acid and 112 mg (0.68 mmol) of CDI into 2 ml of DMF, followed by stirring for 2 hours at room temperature. Resultant mixture was stirred overnight at room temperature. After DMF was distilled off, to the residue was added water and the solution was made alkaline with sodium bicarbonate, which was then extracted with methylene chloride. After washed with saturated saline solution and dried over anhydrous magnesium sulfate, the solution was concentrated under reduced pressure to obtain crude oil. This was subjected to silica gel column chromatographic purification (methylene chloride:acetone=5:1) to obtain 37 mg (17.3%) of aimed compound. m.p. 139°-141° C.

1. additionThis solution was added to another solution which
2. customwas separately prepared
3. stirringby stirring for 2 hours at room temperature
4. stirringResultant mixture was stirred overnight at room temperature
5. distillationAfter DMF was distilled off, to the residue
6. additionwas added water
7. extractionwas then extracted with methylene chloride
8. washAfter washed with saturated saline solution
9. dry with materialdried over anhydrous magnesium sulfate
10. concentrationthe solution was concentrated under reduced pressure
11. customto obtain crude oil
12. customThis was subjected to silica gel column chromatographic purification (methylene chloride:acetone=5:1)

ORD record

ord-62f1145280f043c8acb078038cc644fd

Source dataset

uspto-grants-1995_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05449787