Phenyl isocyanate → HCID 86612253, compound

HRID 1623122Notes

Reaction equation

HRID 1623122 reaction equation
[CH3:1][O:2][NH:3][CH:4]([CH3:24])[CH2:5][CH2:6][CH2:7][N:8]1[C:20]2[C:19]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[N:13]=[CH:12][C:11]=2[N:10]=[C:9]1[CH2:21][CH2:22][CH3:23].[C:25]1([N:31]=[C:32]=[O:33])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>O1CCCC1>[CH2:21]([C:9]1[N:8]([CH2:7][CH2:6][CH2:5][CH:4]([N:3]([O:2][CH3:1])[C:32]([NH:31][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[O:33])[CH3:24])[C:20]2[C:19]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[N:13]=[CH:12][C:11]=2[N:10]=1)[CH2:22][CH3:23]

Participants

4

Reactant 2

HCID 7672Phenyl isocyanateHCID 86612250HCID 86612250, compound2×

Product 1

HCID 86612253HCID 86612253, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The preparation of O-methyl-N-[1-methyl-4-(2-propyl-1H-imidazo-[4,5-c]quinolin-1-yl)butyl]hydroxylamine is described in parts A-D of Example 10. Phenyl isocyanate (0.49 mL, 4.59 mmol) was added to a solution of O-methyl-N-[1-methyl-4-(2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)butyl]hydroxylamine (1.0 g, 3.06 mmol) in tetrahydrofuran (THF) (20 mL) and stirred for 4 hours at ambient temperature. The reaction mixture was concentrated under reduced pressure to afford 1.02 g of 1-[4-(2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)-1-methylbutyl]-1-methoxy-3-phenylurea which was used without any further purification.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-9d0f844fd1694e3bb68d7a84d123d532
Source dataset
uspto-grants-2014_07
Patent number
US08778963B2

Reaction notes

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