Toluene → N-(4-(6-Cyano-7-(2-methoxyethoxy)-4-quinolyl)oxy-2-fluorophenyl)-N'-(3-(methylsulfonyl)phenyl)urea

HRID 853229Notes

Reaction equation

HRID 853229 reaction equation
[NH2:1][C:2]1[CH:25]=[CH:24][C:5]([O:6][C:7]2[C:16]3[C:11](=[CH:12][C:13]([O:19][CH2:20][CH2:21][O:22][CH3:23])=[C:14]([C:17]#[N:18])[CH:15]=3)[N:10]=[CH:9][CH:8]=2)=[CH:4][C:3]=1[F:26].[CH3:27][S:28]([C:31]1[CH:32]=[C:33]([NH:37][C:38](=O)[O:39]C2C=CC=CC=2)[CH:34]=[CH:35][CH:36]=1)(=[O:30])=[O:29].C1(C)C=CC=CC=1.C(N(C(C)C)CC)(C)C>C(OCC)(=O)C>[C:17]([C:14]1[CH:15]=[C:16]2[C:11](=[CH:12][C:13]=1[O:19][CH2:20][CH2:21][O:22][CH3:23])[N:10]=[CH:9][CH:8]=[C:7]2[O:6][C:5]1[CH:24]=[CH:25][C:2]([NH:1][C:38]([NH:37][C:33]2[CH:34]=[CH:35][CH:36]=[C:31]([S:28]([CH3:27])(=[O:30])=[O:29])[CH:32]=2)=[O:39])=[C:3]([F:26])[CH:4]=1)#[N:18]

Participants

6

Reactant 4

HCID 1140TolueneHCID 81531DiisopropylethylamineHCID 22936234Phenyl 3-methylsulfonylphenylcarbamateHCID 229362984-(4-Amino-3-fluorophenoxy)-6-cyano-7-(2-methoxyethoxy)quinoline

Product 1

HCID 22936363N-(4-(6-Cyano-7-(2-methoxyethoxy)-4-quinolyl)oxy-2-fluorophenyl)-N'-(3-(methylsulfonyl)phenyl)ureaYield 8%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

4-(4-Amino-3-fluorophenoxy)-6-cyano-7-(2-methoxyethoxy)quinoline (106 mg) and phenyl N-(3-(methylsulfonyl)phenyl)carbamate (96 mg) were added to 5 ml of toluene, and then 0.06 ml of diisopropylethylamine was added and the mixture was heated to reflux for 3 hours. After cooling, ethyl acetate was added and the precipitated insoluble portion was filtered out. The filtrate was concentrated, the resulting residue was dissolved in tetrahydrofuran, toluene was added, and the precipitated solid was filtered out to obtain 13 mg of the title compound as light brown crystals (8% yield).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 3 hours
  3. temperatureAfter cooling
  4. filtrationthe precipitated insoluble portion was filtered out
  5. concentrationThe filtrate was concentrated
  6. dissolutionthe resulting residue was dissolved in tetrahydrofuran
  7. additiontoluene was added
  8. filtrationthe precipitated solid was filtered out

Sources & evidence

ORD record
ord-083b0fd6f75e426d888879e1c7d0022e
Source dataset
uspto-grants-2007_08
Patent number
US07253286B2

Reaction notes

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