Toluene → N-{4-[(6,7-Dimethoxy-4-quinolyl)oxy]-2-fluorophenyl}-N'-[3-(methylsulfanyl)propanoyl]thiourea

HRID 721843Notes

Reaction equation

HRID 721843 reaction equation
[CH3:1]SCCC(Cl)=O.[CH3:8][S:9][CH2:10][CH2:11][C:12]([N:14]=[C:15]=[S:16])=[O:13].[CH3:17][O:18][C:19]1[CH:20]=[C:21]2[C:26](=[CH:27][C:28]=1[O:29][CH3:30])[N:25]=[CH:24]N=[C:22]2[O:31][C:32]1[CH:38]=[CH:37][C:35]([NH2:36])=[C:34]([F:39])[CH:33]=1.C1(C)C=CC=CC=1>C(O)C>[CH3:8][S:9][CH2:10][CH2:11][C:12]([N:14]=[C:15]=[S:16])=[O:13].[CH3:17][O:18][C:19]1[CH:20]=[C:21]2[C:26](=[CH:27][C:28]=1[O:29][CH3:30])[N:25]=[CH:24][CH:1]=[C:22]2[O:31][C:32]1[CH:38]=[CH:37][C:35]([NH:36][C:15]([NH:14][C:12](=[O:13])[CH2:11][CH2:10][S:9][CH3:8])=[S:16])=[C:34]([F:39])[CH:33]=1

Participants

7

Reactant 4

HCID 1140TolueneHCID 129214403-(Methylthio)propionyl ChlorideHCID 218900903-(Methylsulfanyl)propanoyl isothiocyanateHCID 218902744-((6,7-Dimethoxy-4-quinazolinyl)oxy]-2-fluoroaniline

Product 2

HCID 21890084N-{4-[(6,7-Dimethoxy-4-quinolyl)oxy]-2-fluorophenyl}-N'-[3-(methylsulfanyl)propanoyl]thioureaYield 57%HCID 218900903-(Methylsulfanyl)propanoyl isothiocyanate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

3-(Methylsulfanyl)propanoyl isothiocyanate was prepared using commercially available 3-(methylsulfanyl)propanoyl chloride (80 mg) as a starting compound according to the description of the literature. 3-(Methylsulfanyl)propanoyl isothiocyanate was dissolved in ethanol (1 ml) to prepare a solution. 4-[(6,7-Dimethoxy-4-quinazolinyl)oxy]-2-fluoroaniline (50 mg), toluene (5 ml), and ethanol (1 ml) were added to the solution, and the mixture was stirred at room temperature for 2 hr. The reaction solution was concentrated, and the residue was purified by chromatography on silica gel using chloroform/acetone for development to give the title compound (43 mg, yield 57%).

Workup

  1. customto prepare a solution
  2. concentrationThe reaction solution was concentrated
  3. customthe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-b397fe7aca5141d49972a38e4da2e87d
Source dataset
uspto-grants-2006_11
Patent number
US07135466B2

Reaction notes

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