Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Propyl methanesulfonate | HCID 74705 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | HCID 67619063 | HCID 67619063 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 67619068 | HCID 67619068 | 27.9% |
Reaction Steps
Into 2 ml of DMF were dissolved 200 mg (0.68 mmol) of cis-3-amino-4-methyl-1-(1-methylindazol-3-ylcarbonyl)pyrrolidine hydrochloride and 0.11 ml (0.81 mmol) of triethylamine, and 188 mg (1.36 mmol) of n-propyl methanesulfonate was added under ice cooling. Then, the mixture was stirred for 5 hours at room temperature, for 3 hours at 60° C. and further for 5 hours at 70° C. After addition of water, 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:methanol=20:1) to obtain 57 mg (27.9%) of aimed compound (pale yellow oil).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US05449787 |
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| Source dataset | uspto-grants-1995_09 |
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| ORD ID | ord-d23e2156380046fdbdd899db325f0639 |
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| Source note | uspto-grants-1995_09 |
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