Trifluoroacetic acid → HCID 10135483, compound

HRID 1839168Notes

Reaction equation

HRID 1839168 reaction equation
[CH:1]1([NH:4][C:5]([C:7]2[C:16](=[O:17])[C:15]3[C:10](=[N:11][CH:12]=[CH:13][CH:14]=3)[N:9]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([C:24]4[CH:25]=[N:26][C:27]([O:30]CC5C=CC=CC=5)=[CH:28][CH:29]=4)[CH:19]=3)[CH:8]=2)=[O:6])[CH2:3][CH2:2]1.FC(F)(F)C(O)=O>ClCCCl.C(Cl)Cl.C(=O)(O)[O-].[Na+]>[CH:1]1([NH:4][C:5]([C:7]2[C:16](=[O:17])[C:15]3[C:10](=[N:11][CH:12]=[CH:13][CH:14]=3)[N:9]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([C:24]4[CH:29]=[CH:28][C:27](=[O:30])[NH:26][CH:25]=4)[CH:19]=3)[CH:8]=2)=[O:6])[CH2:3][CH2:2]1

Participants

6

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 10299946HCID 10299946, compound

Product 1

HCID 10135483HCID 10135483, compound

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of N-cyclopropyl-1-[3-(6-benzyloxypyridin-3-yl)phenyl]-1,4-dihydro[1,8]naphthyridin-4-one-3-carboxamide from Example 42 in 1,2-dichloroethane (25 ml/mmol) was added trifluoroacetic acid (1.5 ml/mmol) and the resulting mixture was stirred at 60° C. for 18 hours. More trifluoroacetic acid was added (0.75 ml/mmol) and heating was continued for a further 24 hours. The cooled mixture was diluted with methylene chloride and saturated aqueous sodium bicarbonate was added, resulting in precipitation of a solid which was filtered. From the filtrate the organic phase was collected and evaporated to a solid which was combined with the previous filtered solid. This mixture was chromatographed on silica gel eluting with 10% methanol in methylene chloride to afford the title compound as a white fluffy solid.

Workup

  1. temperatureheating
  2. waitwas continued for a further 24 hours
  3. additionwas added
  4. customresulting in precipitation of a solid which
  5. filtrationwas filtered
  6. customFrom the filtrate the organic phase was collected
  7. customevaporated to a solid which
  8. filtrationprevious filtered solid
  9. customThis mixture was chromatographed on silica gel eluting with 10% methanol in methylene chloride

Sources & evidence

ORD record
ord-4c56c4bdf32c46c28afaa7fc15a70999
Source dataset
uspto-grants-2004_01
Patent number
US06677351B2

Reaction notes

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