Dimethylformamide → HCID 67618774, compound
Reaction equation
Cl.N[C@H]1[C@@H](C)CN(C23C(C)(C)C2CCC([C:19]2[C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[N:21]([CH3:28])[N:20]=2)(C)C3=O)C1.[CH2:30]([N:32]([CH2:35][CH3:36])[CH2:33][CH3:34])[CH3:31].[CH2:37](I)[CH3:38].[CH3:40][N:41]([CH:43]=[O:44])C>>[CH2:30]([N:32]([CH2:35][CH3:36])[C@H:33]1[C@@H:37]([CH3:38])[CH2:40][N:41]([C:43]([C:19]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[N:21]([CH3:28])[N:20]=2)=[O:44])[CH2:34]1)[CH3:31]Participants
Procedure
Into 2 ml of DMF were dissolved 200 mg (0.68 mmol) of cis-3-amino-4-methyl-1-(1-methylindazol-3-ylcaronyl)pyrrolidine hydrochloride and 0.11 ml (0.81 mmol) of triethylamine, and 0.11 ml (1.36 mmol) of ethyl iodide was added dropwise under ice cooling. After stirring overnight at room temperature, insolubles were filtered off. After addition of 40 ml of water, the solution was made alkaline with sodium bicarbonate, which was then extracted with methylene chloride. After 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=10:1) to obtain 100 mg (46.9%) of aimed compound (pale yellow oil).
Workup
- additionwas added dropwise under ice cooling
- filtrationinsolubles were filtered off
- additionAfter addition of 40 ml of water
- extractionwas then extracted with methylene chloride
- dry with materialAfter dried over anhydrous magnesium sulfate
- concentrationthe solution was concentrated under reduced pressure
- customto obtain crude oil
- customThis was subjected to silica gel column chromatographic purification (methylene chloride:methanol=10:1)
Sources & evidence
- ORD record
- ord-821360a61ff44cbca60ac83c365f222c
- Source dataset
- uspto-grants-1995_09
- Patent number
- US05449787
Reaction notes
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