Cyclohexyl isocyanate → HCID 9979787, compound

HRID 431491Notes

Reaction equation

HRID 431491 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[CH2:21][CH3:22].[CH:23]1([N:29]=[C:30]=[O:31])[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1>N1C=CC=CC=1>[NH2:20][C:11]1[C:10]2[N:9]=[C:8]([CH2:21][CH3:22])[N:7]([CH2:6][CH2:5][O:4][CH2:3][CH2:2][NH:1][C:30]([NH:29][CH:23]3[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]3)=[O:31])[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 10108776HCID 10108776, compound

Product 1

HCID 9979787HCID 9979787, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of the compound of Example 46, 1-[2-(2-aminoethoxy)ethyl]-2-ethyl-1H-imidazo[4,5-c]quinolin-4-amine (800 mg, 2.67 mmol) in 30 mL of pyridine was chilled in an ice water bath. With vigorous stirring, the solution was treated with cyclohexyl isocyanate (0.340 mL, 2.67 mmol). After 1 h, the reaction was concentrated to yield an off white solid. Purification by column chromatography (SiO2, 95:5:0.5 CHCl3:MeOH:NH4OH) gave 748 mg of N-{2-[2-(4-amino-2-ethyl-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-0a3e09bfa9f74010bcebf7132f1e1522
Source dataset
uspto-grants-2003_12
Patent number
US06660735B2

Reaction notes

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