Potassium Carbonate → HCID 22138909, compound

HRID 1825820Notes

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]([CH3:25])[CH3:24]>CN(C)C=O>[CH3:24][N:23]([CH3:25])[CH2:22][CH2:21][N:7]1[CH:6]=[C:5]2[C:9]([CH:10]=[CH:11][CH:12]=[C:4]2[N+:1]([O-:3])=[O:2])=[N:8]1

Participants

Conditions

Temperature: 60 °C

Procedure

4-Nitroindazole (1.00 g, 6.13 mmol) was dissolved in 20 mL of N,N-dimethylformamide and potassium carbonate (2.50 g, 18.1 mmol) was added. The mixture was stirred for 30 minutes and then (2-chloro-ethyl)-dimethyl-amine hydrochloride (1.33 g 9.23 mmol) was added. The reaction mixture was heated to 60° C. for 6 hours, cooled to room temperature. The mixture was filtered through a plug of silica gel and 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) ppm 2.19 (s, 6H), 2.84 (t, 2H, J=6.44) 4.65 (t, 2H, J=6.44), 7.49 (dd, 1H, J1=8.48, J2=7.8), 8.18(m, 1H), 8.20 (m, 1H), 8.91 (s, 1H); MS (DCI/NH3) m/z 235 [M+H]+.

Workup

temperaturecooled to room temperature
filtrationThe mixture was filtered through a plug of silica gel
washrinsed 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-f5cf6da0d1a046adb56d955073c778c2
Source dataset: uspto-grants-2006_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07049307B2

Reaction notes

Loading…