Ammonia → 1-(2-aminoethyl)-1H-imidazo[4,5-c]quinoline-2,4-diamine

HRID 1097600Notes

Reaction equation

[NH2:1][C:2]1[N:3]([CH2:16][CH2:17][NH:18]C(=O)OC(C)(C)C)[C:4]2[C:13]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[N:7]=[C:6](Cl)[C:5]=2[N:15]=1.[NH3:26]>CO>[NH2:18][CH2:17][CH2:16][N:3]1[C:4]2[C:13]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[N:7]=[C:6]([NH2:26])[C:5]=2[N:15]=[C:2]1[NH2:1]

Participants

Conditions

Temperature: 150 °C

Procedure

tert-Butyl 2-(2-amino-4-chloro-1H-imidazo[4,5-c]quinolin-1-yl)ethylcarbamate (3.5 g, 9.7 mmol) and ammonia (approximately 100 mL of a 7 N solution in methanol) were added to a pressure vessel, which was sealed and heated at 150° C. overnight. The volatiles were removed under reduced pressure, and the residue was purified by automated flash chromatography (silica cartridge, eluting with aqueous ammonium hydroxide:methanol:dichloromethane in a gradient from 0:0:100 to 1.5:28.5:70) to provide 840 mg of 1-(2-aminoethyl)-1H-imidazo[4,5-c]quinoline-2,4-diamine as a dark grey solid.

Workup

customwhich was sealed
customThe volatiles were removed under reduced pressure
customthe residue was purified by automated flash chromatography (silica cartridge
washeluting with aqueous ammonium hydroxide

Sources & evidence

ORD record: ord-bd7fc6e343e044c1b5e4e539a9456fb4
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08143270B2

Reaction notes

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