3-Pyridinylboronic acid → HCID 68818533, compound

HRID 9430Notes

Reaction equation

HRID 9430 reaction equation
[CH3:1][CH:2]([S:26]([NH2:29])(=[O:28])=[O:27])[CH2:3][CH2:4][CH2:5][CH2:6][N:7]1[C:19]2[C:18]3[CH:17]=[CH:16][C:15](Br)=[CH:14][C:13]=3[N:12]=[C:11]([NH2:21])[C:10]=2[N:9]=[C:8]1[CH2:22][O:23][CH2:24][CH3:25].[N:30]1[CH:35]=[CH:34][CH:33]=[C:32](B(O)O)[CH:31]=1>>[CH3:1][CH:2]([S:26]([NH2:29])(=[O:28])=[O:27])[CH2:3][CH2:4][CH2:5][CH2:6][N:7]1[C:19]2[C:18]3[CH:17]=[CH:16][C:15]([C:32]4[CH:31]=[N:30][CH:35]=[CH:34][CH:33]=4)=[CH:14][C:13]=3[N:12]=[C:11]([NH2:21])[C:10]=2[N:9]=[C:8]1[CH2:22][O:23][CH2:24][CH3:25]

Participants

3

Reactant 2

HCID 27343783-Pyridinylboronic acidHCID 68818104HCID 68818104, compound

Product 1

HCID 68818533HCID 68818533, compoundYield 27.8%

Procedure

Methyl 5-(4-amino-7-bromo-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)pentane-1-sulfonamide (0.47 g, 0.97 mmol) was coupled with pyridine-3-boronic acid (0.14 g, 1.2 mmol) according to the methods described in Part J of Example 1 and Part H of Example 370. The crude product was purified twice by HPFC (eluting with chloroform:CMA in a gradient from 100:0 to 70:30) and then recrystallized from methanol, isolated by filtration, and dried for 5 days under high vacuum at 100–140° C. to provide 0.13 g of methyl 5-[4-amino-2-ethoxymethyl-7-(pyridin-3-yl)-1H-imidazo[4,5-c]quinolin-1-yl]pentane-1-sulfonamide as a white powder, mp 191–192° C.

Workup

  1. customThe crude product was purified twice by HPFC (
  2. washeluting with chloroform
  3. customCMA in a gradient from 100:0 to 70:30) and then recrystallized from methanol
  4. customisolated by filtration
  5. customdried for 5 days under high vacuum at 100–140° C.

Sources & evidence

ORD record
ord-ce7e2c982b6d4f79bcb6c0ac461bd472
Source dataset
uspto-grants-2006_08
Patent number
US07091214B2

Reaction notes

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