HCID 68817680, compound → 1-(2-methylpropyl)-7-phenethyl-1H-imidazo[4,5-c]quinolin-4-amine

HRID 1818203Notes

Reaction equation

HRID 1818203 reaction equation
[CH3:1][CH:2]([CH3:26])[CH2:3][N:4]1[C:16]2[C:15]3[CH:14]=[CH:13][C:12]([CH:17]=[CH:18][C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)=[CH:11][C:10]=3[N:9]=[C:8]([NH2:25])[C:7]=2[N:6]=[CH:5]1>CO>[CH3:1][CH:2]([CH3:26])[CH2:3][N:4]1[C:16]2[C:15]3[CH:14]=[CH:13][C:12]([CH2:17][CH2:18][C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)=[CH:11][C:10]=3[N:9]=[C:8]([NH2:25])[C:7]=2[N:6]=[CH:5]1

Participants

3

Reactant 1

HCID 68817680HCID 68817680, compound

Product 1

HCID 219840951-(2-methylpropyl)-7-phenethyl-1H-imidazo[4,5-c]quinolin-4-amine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A modification of the method described in Example 123 was used to reduce 1-(2-methylpropyl)-7-styryl-1H-imidazo[4,5-c]quinolin-4-amine (1.2 g, 3.5 mmol). The reaction was carried out in methanol (100 mL) for seven days. The crude product was purified by flash column chromatography on silica gel (eluting with 90:10 chloroform:CMA) followed by recrystallization from acetonitrile to provide 1-(2-methylpropyl)-7-phenethyl-1H-imidazo[4,5-c]quinolin-4-amine as white crystals, mp 172-173° C.

Workup

  1. customThe crude product was purified by flash column chromatography on silica gel (eluting with 90:10 chloroform:CMA)
  2. customfollowed by recrystallization from acetonitrile

Sources & evidence

ORD record
ord-16dad1f347ef4d26a659856284e9c0b2
Source dataset
uspto-grants-2009_10
Patent number
US07598382B2

Reaction notes

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