Toluene → N-Cyclopentylcarbonyl-N'-{4-[(6,7-dimethoxy-4-quinolyl)oxy]-2-fluorophenyl}thiourea

HRID 721839Notes

Reaction equation

HRID 721839 reaction equation
[CH:1]1(C(Cl)=O)CCCC1.[CH:9]1([C:14]([N:16]=[C:17]=[S:18])=[O:15])[CH2:13][CH2:12][CH2:11][CH2:10]1.[CH3:19][O:20][C:21]1[CH:22]=[C:23]2[C:28](=[CH:29][C:30]=1[O:31][CH3:32])[N:27]=[CH:26]N=[C:24]2[O:33][C:34]1[CH:40]=[CH:39][C:37]([NH2:38])=[C:36]([F:41])[CH:35]=1.C1(C)C=CC=CC=1>C(O)C>[CH:9]1([C:14]([N:16]=[C:17]=[S:18])=[O:15])[CH2:13][CH2:12][CH2:11][CH2:10]1.[CH:9]1([C:14]([NH:16][C:17]([NH:38][C:37]2[CH:39]=[CH:40][C:34]([O:33][C:24]3[C:23]4[C:28](=[CH:29][C:30]([O:31][CH3:32])=[C:21]([O:20][CH3:19])[CH:22]=4)[N:27]=[CH:26][CH:1]=3)=[CH:35][C:36]=2[F:41])=[S:18])=[O:15])[CH2:13][CH2:12][CH2:11][CH2:10]1

Participants

7

Reactant 4

HCID 1140TolueneHCID 78284Cyclopentanecarbonyl chlorideHCID 218902744-((6,7-Dimethoxy-4-quinazolinyl)oxy]-2-fluoroanilineHCID 218903501154366-71-8

Product 2

HCID 218903501154366-71-8HCID 21891190N-Cyclopentylcarbonyl-N'-{4-[(6,7-dimethoxy-4-quinolyl)oxy]-2-fluorophenyl}thioureaYield 47%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

1-Cyclopentanecarbonyl isothiocyanate was prepared using commercially available 1-cyclopentanecarbonyl chloride (80 mg) as a starting compound according to the description of the literature. 1-Cyclopentanecarbonyl 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 (35 mg, yield 47%).

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-4ecfc9c34e794f188e7f98e318add0ec
Source dataset
uspto-grants-2006_11
Patent number
US07135466B2

Reaction notes

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