HCID 67050958, compound → HCID 67050980, compound

HRID 2383137Notes

Reaction equation

HRID 2383137 reaction equation
[CH2:1]([C:5]1[N:6]([CH3:32])[C:7]2[C:16]3[CH:15]=[C:14]([O:17][CH2:18][C:19]4[CH:24]=[CH:23][C:22]([O:25][C:26]([F:29])([F:28])[F:27])=[CH:21][CH:20]=4)[CH:13]=[CH:12][C:11]=3[N+:10]([O-])=[CH:9][C:8]=2[N:31]=1)[CH2:2][CH2:3][CH3:4].C(C1[N:38](C)C2C3C=C(OCCCCCCOCCCCC4C=CC=CC=4)C=CC=3[N+]([O-])=CC=2N=1)CCC>>[CH2:1]([C:5]1[N:6]([CH3:32])[C:7]2[C:16]3[CH:15]=[C:14]([O:17][CH2:18][C:19]4[CH:24]=[CH:23][C:22]([O:25][C:26]([F:29])([F:28])[F:27])=[CH:21][CH:20]=4)[CH:13]=[CH:12][C:11]=3[N:10]=[C:9]([NH2:38])[C:8]=2[N:31]=1)[CH2:2][CH2:3][CH3:4]

Participants

3

Reactant 2

HCID 67050958HCID 67050958, compoundHCID 67051142HCID 67051142, compound

Product 1

HCID 67050980HCID 67050980, compound

Procedure

The general method described in Example 61 was followed using 2-butyl-1-methyl-8-{[4-(trifluoromethoxy)benzyl]oxy}-5-oxido-1H-imidazo[4,5-c]quinoline (0.380 g, 0.853 mmol) in lieu of 2-butyl-1-methyl-5-oxido-8-{[6-(4-phenylbutoxy)hexyl]oxy}-1H-imidazo[4,5-c]quinoline. The crude product was purified by column chromatography on silica gel (eluting with 90:10 dichloromethane:methanol) to provide 93.9 mg of 2-butyl-1-methyl-8-{[4-(trifluoromethoxy)benzyl]oxy}-1H-imidazo[4,5-c]quinolin-4-amine as a white powder, mp 219.4-220.2° C.

Workup

  1. customThe crude product was purified by column chromatography on silica gel (eluting with 90:10 dichloromethane:methanol)

Sources & evidence

ORD record
ord-ccd7e0fc3346400eac5720cf55f5cb13
Source dataset
uspto-grants-2012_09
Patent number
US08263594B2

Reaction notes

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