Water → HCID 10455524, compound

HRID 1371320Notes

Reaction equation

HRID 1371320 reaction equation
[C:1]1([N:7]=[C:8]=[S:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:10][CH2:11][CH2:12][CH2:13][N:14]1[C:26]2[C:25]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[N:19]=[C:18]([NH2:27])[C:17]=2[N:16]=[C:15]1[CH2:28][CH2:29][CH2:30][CH3:31].O.C(=O)([O-])[O-].[K+].[K+]>CN1CCCC1=O>[NH2:27][C:18]1[C:17]2[N:16]=[C:15]([CH2:28][CH2:29][CH2:30][CH3:31])[N:14]([CH2:13][CH2:12][CH2:11][NH:10][C:8]([NH:7][C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)=[S:9])[C:26]=2[C:25]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[N:19]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7673Phenyl IsothiocyanateHCID 11430Potassium CarbonateHCID 223444131-(3-aminopropyl)-2-butyl-1H-imidazo[4,5-c]quinolin-4-amine

Product 1

HCID 10455524HCID 10455524, compoundYield 65.4%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

Phenyl isothiocyanate (750 mg, 5.55 mmol) was added dropwise with stirring to a chilled (0° C.) solution of 1-(3-aminopropyl)-2-butyl-1H-imidazo[4,5-c]quinolin-4-amine (1.0 g, 3.36 mmol) in 1-methyl-2-pyrrolidinone (50 mL). The reaction mixture was poured into water (500 mL) and the pH adjusted to 10 with solid potassium carbonate. The resulting precipitate was isolated by filtration and then rinsed with water. This material was slurried with hot methanol and then purified by column chromatography (silica gel eluting with 2% methanol in dichloromethane to 7% methanol in dichloromethane). The purified material was recrystallized from isopropanol to provide 950 mg of N-[3-(4-amino-2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)propyl]-N′-phenylthiourea as a white solid, m.p. 142.8–144.0° C. Analysis: Calculated for C24H28N6S. C3H8O: % C, 65.82; % H, 7.37; % N, 17.06; Found: % C, 65.77; % H, 7.41; % N, 17.11.

Workup

  1. customThe resulting precipitate was isolated by filtration
  2. washrinsed with water
  3. custompurified by column chromatography (silica gel eluting with 2% methanol in dichloromethane to 7% methanol in dichloromethane)
  4. customThe purified material was recrystallized from isopropanol

Sources & evidence

ORD record
ord-8fca493e8e9d4831a732dd93fb3ab8c3
Source dataset
uspto-grants-2007_01
Patent number
US07157453B2

Reaction notes

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