7-Bromo-2-(2-methoxyethyl)-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinolin-4-amine → {5-[4-amino-2-(2-methoxyethyl)-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinolin-7-yl]pyridin-3-yl}methanol

HRID 1818136Notes

Reaction equation

HRID 1818136 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[N:15]([CH2:16][CH:17]([CH3:19])[CH3:18])[C:14]([CH2:20][CH2:21][O:22][CH3:23])=[N:13][C:7]=3[C:8]([NH2:12])=[N:9][C:10]=2[CH:11]=1.[Si]([O:31][CH2:32][C:33]1[CH:34]=[C:35](B(O)O)[CH:36]=[N:37][CH:38]=1)(C(C)(C)C)(C)C>>[NH2:12][C:8]1[C:7]2[N:13]=[C:14]([CH2:20][CH2:21][O:22][CH3:23])[N:15]([CH2:16][CH:17]([CH3:19])[CH3:18])[C:6]=2[C:5]2[CH:4]=[CH:3][C:2]([C:35]3[CH:34]=[C:33]([CH2:32][OH:31])[CH:38]=[N:37][CH:36]=3)=[CH:11][C:10]=2[N:9]=1

Participants

3

Reactant 2

HCID 219840247-Bromo-2-(2-methoxyethyl)-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinolin-4-amineHCID 21984252(5-(((tert-Butyldimethylsilyl)oxy)methyl)pyridin-3-yl)boronic acid

Product 1

HCID 11545927{5-[4-amino-2-(2-methoxyethyl)-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinolin-7-yl]pyridin-3-yl}methanol

Procedure

7-Bromo-2-(2-methoxyethyl)-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinolin-4-amine was coupled with 5-(tert-butyldimethylsilanyloxymethyl)pyridine-3-boronic acid according to the method described in Examples 118-121. The reaction was heated at reflux for 2.25 hours, and the work-up procedure described in Part F of Examples 125-131 was followed. The crude product was purified and deprotected according to the procedure described in Example 144. The resulting solid was purified by HPFC (eluting with chloroform:CMA in a gradient from 100:0 to 55:45) followed by recrystallization from acetonitrile to provide {5-[4-amino-2-(2-methoxyethyl)-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinolin-7-yl]pyridin-3-yl}methanol as white needles, mp 202-204° C.

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 2.25 hours
  3. customThe crude product was purified
  4. customThe resulting solid was purified by HPFC (
  5. washeluting with chloroform
  6. customCMA in a gradient from 100:0 to 55:45) followed by recrystallization from acetonitrile

Sources & evidence

ORD record
ord-7abd86e2301a426c8cfed8cf082ef90b
Source dataset
uspto-grants-2009_10
Patent number
US07598382B2

Reaction notes

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