Isopropyl isocyanate → HCID 57515425, compound

HRID 1363576Notes

Reaction equation

HRID 1363576 reaction equation
[CH:1]([N:4]=[C:5]=[O:6])([CH3:3])[CH3:2].[CH2:7]([O:9][CH2:10][C:11]1[N:12]([CH2:24][C:25]2([NH2:31])[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]2)[C:13]2[C:22]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[N:16]=[CH:15][C:14]=2[N:23]=1)[CH3:8]>>[CH2:7]([O:9][CH2:10][C:11]1[N:12]([CH2:24][C:25]2([NH:31][C:5]([NH:4][CH:1]([CH3:3])[CH3:2])=[O:6])[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]2)[C:13]2[C:22]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[N:16]=[CH:15][C:14]=2[N:23]=1)[CH3:8]

Participants

3

Reactant 2

HCID 61277Isopropyl isocyanate2×HCID 575154201-[(2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)methyl]cyclohexylamine2×

Product 1

HCID 57515425HCID 57515425, compound

Procedure

Isopropyl isocyanate (0.15 mL, 1.45 mmol) was added to a solution of 1-{[2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]methyl}cyclohexanamine (0.50 g, 1.45 mmol) dichloromethane (5 mL) at rt. After 4 h, the reaction was set up on a larger scale with 1-{[2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]methyl}cyclohexanamine (1.50 g, 4.43 mmol). Both reactions were allowed to stir overnight and additional isopropyl isocyanate (0.5 equivalent) was added to each reaction. After stirring another day, the reactions were combined and concentrated under reduced pressure to yield an oil. The oil was triturated with hexane and N-(1-{[2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]methyl}cyclohexyl)-N′-isopropylurea was isolated as a white solid (2.23 g, 89%).

Workup

  1. stirringAfter stirring another day
  2. concentrationconcentrated under reduced pressure
  3. customto yield an oil
  4. customThe oil was triturated with hexane

Sources & evidence

ORD record
ord-9f63eba364634980b343d50e6442ece0
Source dataset
uspto-grants-2011_02
Patent number
US07884207B2

Reaction notes

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