Butyl isocyanate → HCID 10408458, compound

HRID 1368139Notes

Reaction equation

HRID 1368139 reaction equation
C(N(CC)CC)C.[NH2:8][CH2:9][CH2:10][CH2:11][N:12]1[C:24]2[C:23]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[N:17]=[C:16]([NH2:25])[C:15]=2[N:14]=[C:13]1[CH2:26][CH2:27][CH2:28][CH3:29].[CH2:30]([N:34]=[C:35]=[O:36])[CH2:31][CH2:32][CH3:33].C(=O)([O-])[O-].[K+].[K+]>CN1CCCC1=O.O>[NH2:25][C:16]1[C:15]2[N:14]=[C:13]([CH2:26][CH2:27][CH2:28][CH3:29])[N:12]([CH2:11][CH2:10][CH2:9][NH:8][C:35]([NH:34][CH2:30][CH2:31][CH2:32][CH3:33])=[O:36])[C:24]=2[C:23]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[N:17]=1

Participants

7

Reactant 4

HCID 8110Butyl isocyanateHCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 223444131-(3-aminopropyl)-2-butyl-1H-imidazo[4,5-c]quinolin-4-amine

Product 1

HCID 10408458HCID 10408458, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

Triethylamine (765 mg, 7.56 mmol) was added to a solution of 1-(3-aminopropyl)-2-butyl-1H-imidazo[4,5-c]quinolin-4-amine (1.5 g, 5.04 mmol) in 1-methyl-2-pyrrolidinone (100 mL). Butyl isocyanate (549 mg, 5.55 mmol) was added dropwise with stirring. The reaction mixture was allowed to stir overnight and then it was poured into water (500 mL). The pH was adjusted to 10 using solid potassium carbonate. The resulting precipitate was isolated by filtration, washed with water and then purified by column chromatography (silica gel eluting with 5% methanol in dichloromethane and then with 10% methanol in dichloromethane. The purified material was recrystallized from acetonitrile to provide 800 mg of N-[3-(4-amino-2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)propyl]-N′-butylurea as a white solid, m.p. 185.5-186.4° C. Analysis: Calculated for C22H32N6O: %C, 66.64; %H, 8.13; %N, 21.29; Found: %C, 66.38; %H, 8.19; %N, 21.10.

Workup

  1. stirringto stir overnight
  2. customThe resulting precipitate was isolated by filtration
  3. washwashed with water
  4. custompurified by column chromatography (silica gel eluting with 5% methanol in dichloromethane
  5. customThe purified material was recrystallized from acetonitrile

Sources & evidence

ORD record
ord-af887c163d074d998469a27df6e7bfd7
Source dataset
uspto-grants-2003_06
Patent number
US06573273B1

Reaction notes

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