Toluene → HCID 21891173, compound

HRID 721832Notes

Reaction equation

HRID 721832 reaction equation
C1(C(Cl)=O)CC1.[CH:7]1([C:10]([N:12]=[C:13]=[S:14])=[O:11])[CH2:9][CH2:8]1.[CH3:15][O:16][C:17]1[CH:18]=[C:19]2[C:24](=[CH:25][C:26]=1[O:27][CH3:28])[N:23]=[CH:22][CH:21]=[C:20]2[O:29][C:30]1[CH:36]=[CH:35][C:33]([NH2:34])=[CH:32][C:31]=1[F:37].C1(C)C=CC=CC=1>C(O)C>[CH:7]1([C:10]([N:12]=[C:13]=[S:14])=[O:11])[CH2:9][CH2:8]1.[CH:7]1([C:10]([NH:12][C:13]([NH:34][C:33]2[CH:35]=[CH:36][C:30]([O:29][C:20]3[C:19]4[C:24](=[CH:25][C:26]([O:27][CH3:28])=[C:17]([O:16][CH3:15])[CH:18]=4)[N:23]=[CH:22][CH:21]=3)=[C:31]([F:37])[CH:32]=2)=[S:14])=[O:11])[CH2:9][CH2:8]1

Participants

7

Reactant 4

HCID 1140TolueneHCID 77637Cyclopropanecarbonyl chlorideHCID 114269974-((6,7-Dimethoxyquinolin-4-yl)oxy)-3-fluorobenzenamineHCID 16792372Cyclopropanecarbonyl isothiocyanate

Product 2

HCID 16792372Cyclopropanecarbonyl isothiocyanateHCID 21891173HCID 21891173, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

1-Cyclopropanecarbonyl isothiocyanate was prepared using commercially available 1-cyclopropanecarbonyl chloride (80 mg) as a starting compound according to the description of the literature. 1-Cyclopropanecarbonyl isothiocyanate was dissolved in ethanol (1 ml) to prepare a solution. 4-[(6,7-Dimethoxy-4-quinolyl)oxy]-3-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 (46 mg, yield 66%).

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-99a4c99ec40248fb8eef29811413cef4
Source dataset
uspto-grants-2006_11
Patent number
US07135466B2

Reaction notes

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