Potassium Carbonate → HCID 22138912, compound

HRID 1825815Notes

Reaction equation

[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH:6]=[N:7][NH:8]2)([O-:3])=[O:2].C(=O)([O-])[O-].[K+].[K+].Cl.Cl[CH2:21][CH2:22][N:23]1[CH2:27][CH2:26][CH2:25][CH2:24]1>CN(C)C=O>[N+:1]([C:4]1[C:5]2[C:9]([CH:10]=[CH:11][CH:12]=1)=[N:8][N:7]([CH2:21][CH2:22][N:23]1[CH2:27][CH2:26][CH2:25][CH2:24]1)[CH:6]=2)([O-:3])=[O:2]

Participants

Conditions

Temperature: 60 °C

Procedure

4-Nitroindazole (3.00 g, 18.4 mmol) was dissolved in 60 mL of N,N-dimethylformamide and potassium carbonate (7.50 g, 54.3 mmol) was added. The mixture was stirred for 30 minutes and then 1-(2-chloro-ethyl)-pyrrolidine hydrochloride (4.80 g 28.2 mmol) was added. The reaction mixture was heated to 60° C. for 6 hours, cooled to room temperature and the mixture filtered through a plug of silica gel which was rinsed with triethylamine/ethyl acetate (1/4). The filtrate was concentrated in vacuo to remove N,N-dimethylformamide and the residue purified by flash chromatography (silica gel, triethylamine/ethyl acetate 1/30). 1H NMR (300 MHz, DMSO-d6) δ ppm 1.64 (m, 4H), 2.48 (m, 4H), 3.01 (t, 2H, J=6.44), 4.67 (t, 2H, J=6.44), 7.49 (t, 1H, J=8.14), 8.19 (d, 2H, J=7.80), 8.92 (s, 1H); MS (DCI/NH3) m/z 261 [M+H]+.

Workup

temperaturecooled to room temperature
filtrationthe mixture filtered through a plug of silica gel which
washwas rinsed with triethylamine/ethyl acetate (1/4)
concentrationThe filtrate was concentrated in vacuo
customto remove N,N-dimethylformamide
customthe residue purified by flash chromatography (silica gel, triethylamine/ethyl acetate 1/30)

Sources & evidence

ORD record: ord-9c3447afc8504092b513ae4b8d39c46e
Source dataset: uspto-grants-2006_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07049307B2

Reaction notes

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