3-Methoxypropanoyl chloride → 1-[7-bromo-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-1-yl]-2-methylpropan-2-ol

HRID 9383Notes

Reaction equation

HRID 9383 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[NH:12][CH2:13][C:14]([CH3:17])([OH:16])[CH3:15])=[CH:9][CH:8]=[C:7]([Br:18])[CH:6]=2.[CH3:19][O:20][CH2:21][CH2:22][C:23](Cl)=O>>[Br:18][C:7]1[CH:8]=[CH:9][C:10]2[C:11]3[N:12]([CH2:13][C:14]([CH3:15])([OH:16])[CH3:17])[C:23]([CH2:22][CH2:21][O:20][CH3:19])=[N:1][C:2]=3[CH:3]=[N:4][C:5]=2[CH:6]=1

Participants

3

Reactant 2

HCID 27597283-Methoxypropanoyl chlorideHCID 219844571-(3-Amino-7-bromoquinolin-4-ylamino)-2-methylpropan-2-ol

Product 1

HCID 219843361-[7-bromo-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-1-yl]-2-methylpropan-2-olYield 37.6%

Procedure

The method described in Part A of Example 9 was used to react 1-(3-amino-7-bromoquinolin-4-ylamino)-2-methylpropan-2-ol (29.0 g, 93.5 mmol) with 3-methoxypropionyl chloride (11.5 g, 93.5 mmol). The crude product was recrystallized from 2:1 ethyl acetate:hexane and then purified by flash column chromatography on silica gel (eluting sequentially with 60:40 acetone:toluene and acetone). The resulting solid was recystallized from 3:1 ethyl acetate hexane to provide 13.3 g of 1-[7-bromo-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-1-yl]-2-methylpropan-2-ol as translucent crystals.

Workup

  1. customThe crude product was recrystallized from 2:1 ethyl acetate
  2. customhexane and then purified by flash column chromatography on silica gel (
  3. washeluting sequentially with 60:40 acetone

Sources & evidence

ORD record
ord-395c3b609d4b49cb8302ff782ff91fc2
Source dataset
uspto-grants-2006_08
Patent number
US07091214B2

Reaction notes

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