3-Methoxypropanoyl chloride → 7-Bromo-2-(2-methoxyethyl)-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinolin-4-amine

HRID 9385Notes

Reaction equation

HRID 9385 reaction equation
COCCC(Cl)=O.[Br:8][C:9]1[CH:10]=[CH:11][C:12]2[C:13]3[N:22]([CH2:23][CH:24]([CH3:26])[CH3:25])[C:21]([CH2:27][CH2:28][O:29][CH3:30])=[N:20][C:14]=3[C:15]([NH2:19])=[N:16][C:17]=2[CH:18]=1.B1([C:37]2[CH:42]=[CH:41][CH:40]=[N:39][CH:38]=2)OCCCO1>>[Br:8][C:9]1[CH:10]=[CH:11][C:12]2[C:13]3[N:22]([CH2:23][CH:24]([CH3:26])[CH3:25])[C:21]([CH2:27][CH2:28][O:29][CH3:30])=[N:20][C:14]=3[C:15]([NH2:19])=[N:16][C:17]=2[CH:18]=1.[CH3:30][O:29][CH2:28][CH2:27][C:21]1[N:22]([CH2:23][CH:24]([CH3:26])[CH3:25])[C:13]2[C:12]3[CH:11]=[CH:10][C:9]([C:37]4[CH:38]=[N:39][CH:40]=[CH:41][CH:42]=4)=[CH:18][C:17]=3[N:16]=[C:15]([NH2:19])[C:14]=2[N:20]=1

Participants

5

Reactant 3

HCID 27597283-Methoxypropanoyl chlorideHCID 41980053-(1,3,2-Dioxaborinan-2-yl)pyridineHCID 219840247-Bromo-2-(2-methoxyethyl)-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinolin-4-amine

Product 2

HCID 219840247-Bromo-2-(2-methoxyethyl)-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinolin-4-amineHCID 219841392-(2-methoxyethyl)-1-(2-methylpropyl)-7-(pyridin-3-yl)-1H-imidazo[4,5-c]quinolin-4-amine

Procedure

7-Bromo-2-(2-methoxyethyl)-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinolin-4-amine was prepared according to the procedures described in Parts A and B of Example 9 using methoxypropanoyl chloride instead of ethoxyacetyl chloride. 7-Bromo-2-(2-methoxyethyl)-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinolin-4-amine was coupled with pyridine-3-boronic acid 1,3-propanediol cyclic ester according to the method described in Examples 118–121. The reaction was heated at reflux overnight, and the work-up procedure described in Part F of Examples 125–131 was followed. The crude product was purified by flash column chromatography on silica gel (eluting with chloroform:CMA in a gradient from 90:10 to 76:24) followed by recrystallization from methanol. The crystals were dried at 1.33 Pa and 98° C. to provide 2-(2-methoxyethyl)-1-(2-methylpropyl)-7-(pyridin-3-yl)-1H-imidazo[4,5-c]quinolin-4-amine as white needles, mp 207–208° C.

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux overnight
  3. customThe crude product was purified by flash column chromatography on silica gel (
  4. washeluting with chloroform
  5. customCMA in a gradient from 90:10 to 76:24) followed by recrystallization from methanol
  6. customThe crystals were dried at 1.33 Pa and 98° C.

Sources & evidence

ORD record
ord-27157f317997486caae24016ad7f66b9
Source dataset
uspto-grants-2006_08
Patent number
US07091214B2

Reaction notes

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