Trifluoroacetic acid → N-(4-((6-cyano-7-(4-piperidylmethoxy)-4-quinolyl)oxy)-2-fluorophenyl)-N'-cyclopropylurea

HRID 388048Notes

Reaction equation

HRID 388048 reaction equation
FC(F)(F)C(O)=O.[C:8]([C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][C:19]=1[O:20][CH2:21][CH:22]1[CH2:27][CH2:26][N:25](C(OC(C)(C)C)=O)[CH2:24][CH2:23]1)[N:16]=[CH:15][CH:14]=[C:13]2[O:35][C:36]1[CH:41]=[CH:40][C:39]([NH:42][C:43]([NH:45][CH:46]2[CH2:48][CH2:47]2)=[O:44])=[C:38]([F:49])[CH:37]=1)#[N:9].O.C(=O)(O)O>C(OCC)(=O)C>[C:8]([C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][C:19]=1[O:20][CH2:21][CH:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1)[N:16]=[CH:15][CH:14]=[C:13]2[O:35][C:36]1[CH:41]=[CH:40][C:39]([NH:42][C:43]([NH:45][CH:46]2[CH2:48][CH2:47]2)=[O:44])=[C:38]([F:49])[CH:37]=1)#[N:9]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 21993411Carbonic acid--water (1/1)HCID 22936270Tert-butyl 4-(((6-cyano-4-(4-(((cyclopropylamino)carbonyl) amino)-3-fluorophenoxy)-7-quinolyl)oxy)methyl)-1-piperidinecarboxylate

Product 1

HCID 22936581N-(4-((6-cyano-7-(4-piperidylmethoxy)-4-quinolyl)oxy)-2-fluorophenyl)-N'-cyclopropylureaYield 113.9%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

After adding 5 ml of trifluoroacetic acid to 340 mg of tert-butyl 4-(((6-cyano-4-(4-(((cyclopropylamino)carbonyl)amino)-3-fluorophenoxy)-7-quinolyl)oxy)methyl)-1-piperidinecarboxylate, the mixture was stirred at room temperature for 7 minutes. Saturated bicarbonate water and ethyl acetate were added to the reaction solution for extraction. The ethyl acetate layer was washed with saline and dried over sodium sulfate. The drying agent was filtered off and the solvent was distilled off under reduced pressure to obtain 320 mg of a light yellow solid.

Workup

  1. washThe ethyl acetate layer was washed with saline
  2. dry with materialdried over sodium sulfate
  3. filtrationThe drying agent was filtered off
  4. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-5e7e04eb69254b268a175bf54b7b8298
Source dataset
uspto-grants-2013_02
Patent number
US08372981B2

Reaction notes

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