Triethylamine → HCID 67619068, compound

HRID 2399550Notes

Reaction equation

Cl.[NH2:2][C@H:3]1[C@@H:7]([CH3:8])[CH2:6][N:5]([C:9]([C:11]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[N:13]([CH3:20])[N:12]=2)=[O:10])[CH2:4]1.C(N(CC)CC)C.CS(O[CH2:33][CH2:34][CH3:35])(=O)=O.C(=O)(O)[O-].[Na+]>O.CN(C=O)C>[CH2:33]([NH:2][C@H:3]1[C@@H:7]([CH3:8])[CH2:6][N:5]([C:9]([C:11]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[N:13]([CH3:20])[N:12]=2)=[O:10])[CH2:4]1)[CH2:34][CH3:35]

Participants

Conditions

Temperature: 70 °C

Procedure

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).

Workup

additionwas added under ice cooling
extractionwas then extracted with methylene chloride
washAfter washed with saturated saline solution
dry with materialdried 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=20:1)

Sources & evidence

ORD record: ord-d23e2156380046fdbdd899db325f0639
Source dataset: uspto-grants-1995_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05449787

Reaction notes

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