7-benzyloxy-1-(2-methylpropyl)-2-propyl-1H-imidazo[4,5-c]quinolin-4-amine → N-[2-(4-amino-2-ethoxymethyl-7-hydroxy-1H-imidazo[4,5-c]quinolin-1-yl)-1,1-dimethylethyl]methanesulfonamide

HRID 598292Notes

Reaction equation

HRID 598292 reaction equation
[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:24][O:25][CH2:26][CH3:27])[N:14]([CH2:15][C:16]([NH:19][S:20]([CH3:23])(=[O:22])=[O:21])([CH3:18])[CH3:17])[C:10]=2[C:9]2[CH:8]=[CH:7][C:6]([O:28]CC3C=CC=CC=3)=[CH:5][C:4]=2[N:3]=1.C(OC1C=CC2C3N(CC(C)C)C(CCC)=NC=3C(N)=NC=2C=1)C1C=CC=CC=1>>[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:24][O:25][CH2:26][CH3:27])[N:14]([CH2:15][C:16]([NH:19][S:20]([CH3:23])(=[O:22])=[O:21])([CH3:18])[CH3:17])[C:10]=2[C:9]2[CH:8]=[CH:7][C:6]([OH:28])=[CH:5][C:4]=2[N:3]=1

Participants

3

Reactant 2

HCID 113612427-benzyloxy-1-(2-methylpropyl)-2-propyl-1H-imidazo[4,5-c]quinolin-4-amineHCID 57545342N-[2-(4-amino-7-benzyloxy-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)-1,1-dimethylethyl]methanesulfonamide

Product 1

HCID 136075196N-[2-(4-amino-2-ethoxymethyl-7-hydroxy-1H-imidazo[4,5-c]quinolin-1-yl)-1,1-dimethylethyl]methanesulfonamideYield 40.3%

Procedure

The general method described in Example 5 was followed using N-[2-(4-amino-7-benzyloxy-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)-1,1-dimethylethyl]methanesulfonamide (1.00 g, 2.01 mmol) in lieu of 7-benzyloxy-1-(2-methylpropyl)-2-propyl-1H-imidazo[4,5-c]quinolin-4-amine. The crude product was recrystallized from methanol (20 mL). The crystals were collected in three crops and washed with methanol and ethyl acetate. The crops were combined and purified by column chromatography on silica gel (eluting with 89.1:9.9:1 chloroform:methanol:ammonium hydroxide) to provide 330 mg of N-[2-(4-amino-2-ethoxymethyl-7-hydroxy-1H-imidazo[4,5-c]quinolin-1-yl)-1,1-dimethylethyl]methanesulfonamide as a white powder, mp 255-256° C. 1H NMR (300 MHz, DMSO-d6, 350K) δ 9.18 (br s, 1H), 8.09 (d, J=8.9 Hz, 1H), 7.00 (br s, 1H), 6.96 (d, J=2.5 Hz, 1H), 6.77 (dd, J=8.9, 2.5 Hz, 1H), 6.11 (s, 2H), 4.84 (s, 2H), 4.81 (s, 2H), 3.56 (q, J=7.0 Hz, 2H), 2.97 (s, 3H), 1.29 (s, 6H), 1.15 (t, J=7.0 Hz, 3H);

Workup

  1. customThe crude product was recrystallized from methanol (20 mL)
  2. customThe crystals were collected in three crops
  3. washwashed with methanol and ethyl acetate
  4. custompurified by column chromatography on silica gel (eluting with 89.1:9.9:1 chloroform:methanol:ammonium hydroxide)

Sources & evidence

ORD record
ord-b163400cca994b02820b22de335881ab
Source dataset
uspto-grants-2011_03
Patent number
US07897597B2

Reaction notes

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