N-{2-[7-(benzyloxy)-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]-1,1-dimethylethyl}-N-isopropylurea → N-[2-(7-benzyloxy-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)-1,1-dimethylethyl]-N'-isopropylurea

HRID 540875Notes

Reaction equation

HRID 540875 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[NH:12][CH2:13][C:14]([NH:17][C:18]([NH:20][CH:21]([CH3:23])[CH3:22])=[O:19])([CH3:16])[CH3:15])=[CH:9][CH:8]=[C:7]([O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[CH:6]=2.[CH2:32]([O:39][C:40]1C=CC2C3N(CC(N(C(C)C)C(N)=O)(C)C)C(COCC)=NC=3C=NC=2[CH:49]=1)[C:33]1C=CC=CC=1>C1(C)C=CC=CC=1>[CH2:25]([O:24][C:7]1[CH:8]=[CH:9][C:10]2[C:11]3[N:12]([CH2:13][C:14]([NH:17][C:18]([NH:20][CH:21]([CH3:23])[CH3:22])=[O:19])([CH3:16])[CH3:15])[C:33]([CH2:32][O:39][CH2:40][CH3:49])=[N:1][C:2]=3[CH:3]=[N:4][C:5]=2[CH:6]=1)[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

4

Reactant 2

HCID 68968716N-{2-[7-(benzyloxy)-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]-1,1-dimethylethyl}-N-isopropylureaHCID 69507214N-(2-{[3-amino-7-(benzyloxy)quinolin-4-yl]amino}-1,1-dimethylethyl)-N'-isopropylurea2×

Product 1

HCID 67051122N-[2-(7-benzyloxy-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)-1,1-dimethylethyl]-N'-isopropylurea

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The material from Part B was combined with N-(2-{[3-amino-7-(benzyloxy)quinolin-4-yl]amino}-1,1-dimethylethyl)-N′-isopropylurea from another experiment, suspended in toluene, and concentrated under reduced pressure. The N-(2-{[3-amino-7-(benzyloxy)quinolin-4-yl]amino}-1,1-dimethylethyl)-N′-isopropylurea (4.57 g, 10.8 mmol) was converted into N-{2-[7-(benzyloxy)-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]-1,1-dimethylethyl}-N-isopropylurea using the method described in Part D of Example 45. The crude product was purified using flash chromatography (silica gel, elution with 6% methanol in dichloromethane) to afford 3.81 g of N-{2-[7-(benzyloxy)-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]-1,1-dimethylethyl}-N′-isopropylurea as an off white solid.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe crude product was purified
  3. washflash chromatography (silica gel, elution with 6% methanol in dichloromethane)

Sources & evidence

ORD record
ord-906fa5f3432d4170b3e3a00e38588539
Source dataset
uspto-grants-2014_10
Patent number
US08871782B2

Reaction notes

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