4-methoxybenzyl 4-[4-amino-2-ethoxymethyl-7-(pyridin-3-yl)-1H-imidazo[4,5-c]quinolin-1-yl]butane-1-sulfonamide → 4-[4-amino-2-ethoxymethyl-7-(pyridin-3-yl)-1H-imidazo[4,5-c]quinolin-1-yl]butane-1-sulfonamide

HRID 9424Notes

Reaction equation

HRID 9424 reaction equation
COC1C=CC(C[CH:8]([S:36]([NH2:39])(=[O:38])=[O:37])[CH2:9][CH2:10][CH2:11][N:12]2[C:24]3[C:23]4[CH:22]=[CH:21][C:20]([C:25]5[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=5)=[CH:19][C:18]=4[N:17]=[C:16]([NH2:31])[C:15]=3[N:14]=[C:13]2[CH2:32][O:33][CH2:34][CH3:35])=CC=1>FC(F)(F)C(O)=O>[NH2:31][C:16]1[C:15]2[N:14]=[C:13]([CH2:32][O:33][CH2:34][CH3:35])[N:12]([CH2:11][CH2:10][CH2:9][CH2:8][S:36]([NH2:39])(=[O:38])=[O:37])[C:24]=2[C:23]2[CH:22]=[CH:21][C:20]([C:25]3[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=3)=[CH:19][C:18]=2[N:17]=1

Participants

3

Reactant 1

HCID 688190684-methoxybenzyl 4-[4-amino-2-ethoxymethyl-7-(pyridin-3-yl)-1H-imidazo[4,5-c]quinolin-1-yl]butane-1-sulfonamide

Product 1

HCID 219840384-[4-amino-2-ethoxymethyl-7-(pyridin-3-yl)-1H-imidazo[4,5-c]quinolin-1-yl]butane-1-sulfonamideYield 77.5%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 4-methoxybenzyl 4-[4-amino-2-ethoxymethyl-7-(pyridin-3-yl)-1H-imidazo[4,5-c]quinolin-1-yl]butane-1-sulfonamide (0.50 g, 0.88 mmol) in trifluoroacetic acid (5 mL) was stirred at ambient temperature for four hours and then concentrated under reduced pressure. The residue was dissolved in methanol and concentrated under reduced pressure; this process was repeated three times. The residue was then suspended in water, and 2 M aqueous sodium hydroxide was added to adjust to pH 7. The mixture was stirred for 30 minutes, and the resulting solid was isolated by filtration, washed with water, and purified by HPFC (eluting with chloroform:CMA in a gradient from 100:0 to 30:70). The purified product was dried overnight under high vacuum at 80° C. to provide 0.31 g of 4-[4-amino-2-ethoxymethyl-7-(pyridin-3-yl)-1H-imidazo[4,5-c]quinolin-1-yl]butane-1-sulfonamide as tan needles, mp 250–251.5° C.

Workup

  1. concentrationconcentrated under reduced pressure
  2. dissolutionThe residue was dissolved in methanol
  3. concentrationconcentrated under reduced pressure
  4. addition2 M aqueous sodium hydroxide was added
  5. customthe resulting solid was isolated by filtration
  6. washwashed with water
  7. custompurified by HPFC (
  8. washeluting with chloroform
  9. customThe purified product was dried overnight under high vacuum at 80° C.

Sources & evidence

ORD record
ord-24b232e9b29f4e4097636a3ef525cd72
Source dataset
uspto-grants-2006_08
Patent number
US07091214B2

Reaction notes

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