3-Pyridyl isothiocyanate → HCID 9890753, compound

HRID 1368128Notes

Reaction equation

HRID 1368128 reaction equation
[CH:1]1[CH:6]=[N:5][CH:4]=[C:3]([N:7]=[C:8]=[S:9])[CH:2]=1.[NH2:10][CH2:11][CH2:12][CH2:13][CH2:14][N:15]1[C:27]2[C:26]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[N:20]=[C:19]([NH2:28])[C:18]=2[N:17]=[C:16]1[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>C(Cl)(Cl)Cl.N1C=CC=CC=1>[NH2:28][C:19]1[C:18]2[N:17]=[C:16]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[N:15]([CH2:14][CH2:13][CH2:12][CH2:11][NH:10][C:8]([NH:7][C:3]3[CH:4]=[N:5][CH:6]=[CH:1][CH:2]=3)=[S:9])[C:27]=2[C:26]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[N:20]=1

Participants

5

Reactant 2

HCID 27372423-Pyridyl isothiocyanateHCID 121489921-(4-aminobutyl)-2-phenyl-1H-imidazo[4,5-c]quinolin-4-amine

Product 1

HCID 9890753HCID 9890753, compoundYield 42.8%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6212ChloroformSolvent2×

Procedure

A solution of pyridine-3-isothiocyanate (0.136 g, 1.0 mmol) in chloroform (5 mL) was added at ambient temperature to a solution of 1-(4-aminobutyl)-2-phenyl-1H-imidazo[4,5-c]quinolin-4-amine (0.331 g, 1.0 mmol) in a mixture of chloroform (25 mL) and pyridine (5 mL). The reaction mixture was maintained at ambient temperature over the weekend. The reaction was quenched with ethanol and then concentrated under vacuum to provide an off-white solid. This material was purified by flash chromatography (silica gel, eluting with 10% methanol in dichloromethane). The pure fractions were combined and concentrated under vacuum to provide 0.2 g of N-[4-(4-amino-2-phenyl-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-N′-(3-pyridyl)thiourea as a white solid, m.p. 118-120° C. Mass spec M+1=468.3. Analysis: Calculated for C26H25N7S: %C, 66.79; %H, 5.39; %N, 20.97; Found: %C, 64.29; %H, 5.46; %N, 20.06.

Workup

  1. customThe reaction was quenched with ethanol
  2. concentrationconcentrated under vacuum
  3. customto provide an off-white solid
  4. customThis material was purified by flash chromatography (silica gel, eluting with 10% methanol in dichloromethane)
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-c268736bce9147c99b8dd99b345e075b
Source dataset
uspto-grants-2003_06
Patent number
US06573273B1

Reaction notes

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