Pyrrolidine → HCID 66679022, compound

HRID 2221155Notes

Reaction equation

Cl[CH2:2][CH2:3][N:4]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([C:14]3[C:18]([C:19]4[CH:24]=[CH:23][CH:22]=[C:21]([CH3:25])[N:20]=4)=[N:17][N:16]4[CH2:26][CH2:27][CH2:28][C:15]=34)[CH:12]=2)[N:7]=[CH:6][C:5]1=[O:29].[NH:30]1[CH2:34][CH2:33][CH2:32][CH2:31]1>O1CCOCC1.C(Cl)(Cl)Cl.C(O)(C)C>[CH3:25][C:21]1[N:20]=[C:19]([C:18]2[C:14]([C:11]3[CH:12]=[C:13]4[C:8]([NH:7][CH2:6][C:5](=[O:29])[N:4]4[CH2:3][CH2:2][N:30]4[CH2:34][CH2:33][CH2:32][CH2:31]4)=[CH:9][CH:10]=3)=[C:15]3[CH2:28][CH2:27][CH2:26][N:16]3[N:17]=2)[CH:24]=[CH:23][CH:22]=1

Participants

Conditions

Temperature: 110 °C

Procedure

Combine 1-(2-chloro-ethyl)-7-[2-[6-methyl-(pyridin-2-yl)]-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl]-1H-quinoxalin-2-one (Preparation 7; 60 mg, 0.15 mmol) and pyrrolidine (0.5 ml) in dioxane (5 mL) in a pressure tube. Seal the tube and heat at 110° C. for 40 min. Dilute the reaction mixture with 1:1 chloroform/isopropyl alcohol and wash the solution with saturated sodium chloride solution. Dry the organic phase (sodium sulfate), filter, and concentrate in vacuo. Purify the residue by silica gel chromatography (dichloromethane to 1:1 dichloromethane/methanol) to give 54 mg (84%) of the titled compound. MS ES+ m/e 441 (M+1).

Workup

customSeal the tube
washwash the solution with saturated sodium chloride solution
dry with materialDry the organic phase (sodium sulfate)
filtrationfilter
concentrationconcentrate in vacuo
customPurify the residue by silica gel chromatography (dichloromethane to 1:1 dichloromethane/methanol)

Sources & evidence

ORD record: ord-e0ecdecb54db46878328f4ae7d094b03
Source dataset: uspto-grants-2008_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07368445B2

Reaction notes

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