Thioanisole → HCID 135829401, compound

HRID 387752Notes

Reaction equation

HRID 387752 reaction equation
C([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([O:19][C:20]3[CH:25]=[CH:24][C:23]([NH:26][C:27]([NH:29][C:30]4[S:31][CH:32]=[CH:33][N:34]=4)=[O:28])=[C:22]([F:35])[CH:21]=3)=[CH:14][CH:15]=[N:16]2)=[CH:11][C:10]=1[C:36]#[N:37])C1C=CC=CC=1.C1(SC)C=CC=CC=1>C(O)(C(F)(F)F)=O>[C:36]([C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][C:9]=1[OH:8])[N:16]=[CH:15][CH:14]=[C:13]2[O:19][C:20]1[CH:25]=[CH:24][C:23]([NH:26][C:27]([NH:29][C:30]2[S:31][CH:32]=[CH:33][N:34]=2)=[O:28])=[C:22]([F:35])[CH:21]=1)#[N:37]

Participants

4

Reactant 2

HCID 7520ThioanisoleHCID 22936427HCID 22936427, compound

Product 1

HCID 135829401HCID 135829401, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
70 °C

Procedure

The N-(4-(7-benzyloxy-6-cyanoquinolyl)oxy-2-fluorophenyl)-N′-(2-thiazolyl)urea (5.53 g) synthesized in Example 141 was dissolved in TFA (55 ml), and then thioanisole (5.5 ml) was added and the mixture was heated and stirred at 70° C. for 6 hours. After cooling the reaction solution and concentrating it under reduced pressure, bicarbonate water and methanol were added and the precipitated crystals were filtered. These were washed with diethyl ether to obtain 3.63 g of the title compound (80% yield).

Workup

  1. temperaturethe mixture was heated
  2. temperatureAfter cooling the reaction solution
  3. concentrationconcentrating it under reduced pressure, bicarbonate water and methanol
  4. additionwere added
  5. filtrationthe precipitated crystals were filtered
  6. washThese were washed with diethyl ether

Sources & evidence

ORD record
ord-552b09e598c34ed98db96afcf3941d44
Source dataset
uspto-grants-2013_02
Patent number
US08372981B2

Reaction notes

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