Isopropyl isocyanate → HCID 58833663, compound

HRID 2203555Notes

Reaction equation

HRID 2203555 reaction equation
[CH:1]([N:4]=[C:5]=[O:6])([CH3:3])[CH3:2].[NH2:7][C:8]1[C:17]2[N:18]=[C:19]([CH2:32][O:33][CH2:34][CH3:35])[N:20]([CH2:21][C:22]([NH:25][C:26]([NH:28][CH:29]([CH3:31])[CH3:30])=[O:27])([CH3:24])[CH3:23])[C:16]=2[C:15]2[CH:14]=[CH:13][C:12]([O:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][NH2:43])=[CH:11][C:10]=2[N:9]=1>ClCCl>[NH2:7][C:8]1[C:17]2[N:18]=[C:19]([CH2:32][O:33][CH2:34][CH3:35])[N:20]([CH2:21][C:22]([NH:25][C:26]([NH:28][CH:29]([CH3:31])[CH3:30])=[O:27])([CH3:23])[CH3:24])[C:16]=2[C:15]2[CH:14]=[CH:13][C:12]([O:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][NH:43][C:5]([NH:4][CH:1]([CH3:3])[CH3:2])=[O:6])=[CH:11][C:10]=2[N:9]=1

Participants

4

Reactant 2

HCID 61277Isopropyl isocyanateHCID 69507030HCID 69507030, compound

Product 1

HCID 58833663HCID 58833663, compoundYield 32.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Isopropyl isocyanate (190 μL, 1.93 mmol) was added to a stirred solution of N-{2-[4-amino-7-[(6-aminohexyl)oxy]-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]-1,1-dimethylethyl}-N′-isopropylurea (0.90 g, 1.75 mmol) in dichloromethane (50 mL) at 0° C. After approximately 30 minutes, the solution was allowed to warm to room temperature. A precipitate formed and the mixture was stirred over the weekend. The solvent was removed under reduced pressure and the crude product was purified by flash chromatography (silica gel, gradient elution with 8-10% methanol in dichloromethane) to provide a solid that was dried under vacuum at 60° C. to yield 0.34 g of N-(2-{4-amino-2-(ethoxymethyl)-7-[(6-{[(isopropylamino)carbonyl]amino}hexyl)oxy]-1H-imidazo[4,5-c]quinolin-1-yl}-1,1-dimethylethyl)-N′-isopropylurea as a tan solid, mp 205-209° C.

Workup

  1. customA precipitate formed
  2. customThe solvent was removed under reduced pressure
  3. customthe crude product was purified by flash chromatography (silica gel, gradient elution with 8-10% methanol in dichloromethane)
  4. customto provide a solid
  5. customthat was dried under vacuum at 60° C.

Sources & evidence

ORD record
ord-ad985cb600db48648698f9fdc82b13d5
Source dataset
uspto-grants-2016_06
Patent number
US09365567B2

Reaction notes

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