3-Pyridinylboronic acid → HCID 58681255, compound

HRID 9484Notes

Reaction equation

HRID 9484 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[N:15]([CH2:16][C@@H:17]4[CH2:21][O:20][C:19]([CH3:23])([CH3:22])[O:18]4)[C:14]([CH2:24][O:25][CH2:26][CH3:27])=[N:13][C:7]=3[C:8]([NH2:12])=[N:9][C:10]=2[CH:11]=1.[N:28]1[CH:33]=[CH:32][CH:31]=[C:30](B(O)O)[CH:29]=1>>[CH3:22][C:19]1([CH3:23])[O:18][C@H:17]([CH2:16][N:15]2[C:6]3[C:5]4[CH:4]=[CH:3][C:2]([C:30]5[CH:29]=[N:28][CH:33]=[CH:32][CH:31]=5)=[CH:11][C:10]=4[N:9]=[C:8]([NH2:12])[C:7]=3[N:13]=[C:14]2[CH2:24][O:25][CH2:26][CH3:27])[CH2:21][O:20]1

Participants

3

Reactant 2

HCID 27343783-Pyridinylboronic acidHCID 68818548HCID 68818548, compound

Product 1

HCID 58681255HCID 58681255, compoundYield 65.5%

Procedure

(R)-7-Bromo-1-[(2,2-dimethyl-1,3-dioxolan-4-yl)methyl]-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-4-amine (3.0 g, 6.9 mmol) and pyridine-3-boronic acid (1.02 g, 8.27 mmol) were coupled according to the method described in Examples 118–121. The work-up procedure described in Part F of Examples 125–135 was followed. The crude product was purified by HPFC (eluting with chloroform:CMA in a gradient from 100:0 to 80:20) followed by recrystallization from acetonitrile to provide 1.96 g of (R)-1-[(2,2-dimethyl-1,3-dioxolan-4-yl)methyl]-2-ethoxymethyl-7-(pyridin-3-yl)-1H-imidazo[4,5-c]quinolin-4-amine as a white, crystalline solid, mp 155–156° C.

Workup

  1. customThe crude product was purified by HPFC (
  2. washeluting with chloroform
  3. customCMA in a gradient from 100:0 to 80:20) followed by recrystallization from acetonitrile

Sources & evidence

ORD record
ord-ebe61890eb1d414990c24c6f5dd8ad09
Source dataset
uspto-grants-2006_08
Patent number
US07091214B2

Reaction notes

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