Ethoxyacetyl chloride → 7-bromo-1-cylcohexylmethyl-2-ethoxymethyl-1H-imidazo[4,5-c]quinoline

HRID 9462

Reaction equation

HRID 9462 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([NH:13][CH2:14][CH:15]3[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]3)=[C:7]([NH2:12])[CH:8]=[N:9]2)=[CH:4][CH:3]=1.[CH2:21]([O:23][CH2:24][C:25](Cl)=O)[CH3:22]>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[N:13]([CH2:14][CH:15]4[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]4)[C:22]([CH2:21][O:23][CH2:24][CH3:25])=[N:12][C:7]=3[CH:8]=[N:9][C:10]=2[CH:11]=1

Participants

3

Reactant 2

HCID 84189Ethoxyacetyl chlorideHCID 688178877-Bromo-n4-(cyclohexylmethyl)quinoline-3,4-diamine

Product 1

HCID 1317258897-bromo-1-cylcohexylmethyl-2-ethoxymethyl-1H-imidazo[4,5-c]quinoline

Conditions

Temperature
90 °C

Procedure

A modification of the method described in Part A of Example 9 was used to treat 7-bromo-N4-(cyclohexylmethyl)quinoline-3,4-diamine (7.3 g, 22 mmol) with ethoxyacetyl chloride (2.75 mL, 24.0 mmol). The reaction was heated overnight at 90° C. and then concentrated under reduced pressure to provide 7-bromo-1-cylcohexylmethyl-2-ethoxymethyl-1H-imidazo[4,5-c]quinoline as a dark brown semi-solid.

Workup

  1. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f41eaa09f57b47d7a510a6dea1c16c23
Source dataset
uspto-grants-2006_08
Patent number
US07091214B2

Linked notes

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