Benzenepropanoic acid → HCID 21891079, compound

HRID 721804Notes

Reaction equation

HRID 721804 reaction equation
S(Cl)(Cl)=O.C1(CCC(O)=O)C=CC=CC=1.C1(CCC(Cl)=O)C=CC=CC=1.[C:27]1([CH2:33][CH2:34][C:35]([N:37]=[C:38]=[S:39])=[O:36])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.[CH3:40][O:41][C:42]1[CH:43]=[C:44]2[C:49](=[CH:50][C:51]=1[O:52][CH3:53])[N:48]=[CH:47][CH:46]=[C:45]2[O:54][C:55]1[CH:61]=[CH:60][C:58]([NH2:59])=[CH:57][C:56]=1[F:62]>C(O)C.C1(C)C=CC=CC=1>[CH3:40][O:41][C:42]1[CH:43]=[C:44]2[C:49](=[CH:50][C:51]=1[O:52][CH3:53])[N:48]=[CH:47][CH:46]=[C:45]2[O:54][C:55]1[CH:61]=[CH:60][C:58]([NH:59][C:38]([NH:37][C:35](=[O:36])[CH2:34][CH2:33][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[S:39])=[CH:57][C:56]=1[F:62]

Participants

8

Reactant 5

HCID 107Benzenepropanoic acidHCID 24386Thionyl ChlorideHCID 64801Benzenepropanoyl chlorideHCID 114269974-((6,7-Dimethoxyquinolin-4-yl)oxy)-3-fluorobenzenamineHCID 12279261HCID 12279261, compound

Product 1

HCID 21891079HCID 21891079, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 1140TolueneSolvent2×

Conditions

Temperature
100 °C

Procedure

Toluene (20 ml) and thionyl chloride (1 ml) were added to commercially available 3-phenylpropanoic acid (80 mg), and the mixture was heated at 100° C. for one hr. The solvent was removed by distillation, and 3-phenylpropanoyl isothiocyanate was prepared using the resultant 3-phenylpropanoyl chloride as a starting compound according to the description of the literature. 3-Phenylpropanoyl 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 (57 mg, yield 71%).

Workup

  1. customThe solvent was removed by distillation, and 3-phenylpropanoyl isothiocyanate
  2. customwas prepared
  3. customto prepare a solution
  4. concentrationThe reaction solution was concentrated
  5. customthe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-745fc7d248e14815bbc4684109c854e3
Source dataset
uspto-grants-2006_11
Patent number
US07135466B2

Reaction notes

Loading…