Cyclohexyl isocyanate → HCID 10001607, compound

HRID 1350033Notes

Reaction equation

HRID 1350033 reaction equation
[NH2:1][CH2:2][CH2:3][O:4][CH2:5][CH2:6][N:7]1[C:19]2[C:18]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[N:12]=[C:11]([NH2:20])[C:10]=2[N:9]=[C:8]1[CH3:21].[CH:22]1([N:28]=[C:29]=[O:30])[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1>N1C=CC=CC=1>[NH2:20][C:11]1[C:10]2[N:9]=[C:8]([CH3:21])[N:7]([CH2:6][CH2:5][O:4][CH2:3][CH2:2][NH:1][C:29]([NH:28][CH:22]3[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]3)=[O:30])[C:19]=2[C:18]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[N:12]=1

Participants

4

Reactant 2

HCID 18502Cyclohexyl isocyanateHCID 10401692HCID 10401692, compound

Product 1

HCID 10001607HCID 10001607, compoundYield 49.8%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of the compound of Example 45, 1-[2-(2-aminoethoxy)ethyl]-2-methyl-1H-imidazo[4,5-c]quinolin-4-amine (1.00 g, 3.50 mmol) in 30 ml of pyridine was chilled in an ice water bath. With vigorous stirring, the solution was treated with cyclohexyl isocyanate (0.45 mL, 3.50 mmol). After 18 h, the reaction was concentrated to yield an off white solid. Purification by column chromatography (SiO2, 95:5:0.5 CHCl3:MeOH:NH4OH) gave 716 mg of N-{2-[2-(4-amino-2-methyl-1H-imidazo[4,5-c]quinolin-1-yl)ethoxy]ethyl}-N′-cyclohexylurea as a white solid.

Workup

  1. concentrationthe reaction was concentrated
  2. customto yield an off white solid
  3. customPurification by column chromatography (SiO2, 95:5:0.5 CHCl3:MeOH:NH4OH)

Sources & evidence

ORD record
ord-39915baa4a0c430fbd7fe49764f2b8d1
Source dataset
uspto-grants-2007_05
Patent number
US07214675B2

Reaction notes

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