Trifluoroacetic acid → HCID 118451769, compound

HRID 1054224Notes

Reaction equation

HRID 1054224 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH2:10][O:11][N:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15]([OH:22])=[C:14]([C:23]([NH:25][CH2:26][C:27]([O:29]C(C)(C)C)=[O:28])=[O:24])[C:13]1=[O:34].C(O)(C(F)(F)F)=O>C(Cl)Cl>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH2:10][O:11][N:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15]([OH:22])=[C:14]([C:23]([NH:25][CH2:26][C:27]([OH:29])=[O:28])=[O:24])[C:13]1=[O:34]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 118451757HCID 118451757, compound

Product 1

HCID 118451769HCID 118451769, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirring solution of tert-butyl 2-(1-(benzo[d]thiazol-2-ylmethoxy)-4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxamido)acetate (0.3 g, 0.623 mmol) in DCM (2 ml) was added TFA (3.36 ml, 43.6 mmol) slowly at 20-25° C. Reaction mixture was stirred for 3 h. Excess solvent was distilled out and then diluted with water. Precipitated product was filtered to get crude product which was then recrystallized in EtOH:EtOAC to get titled product in 87% yield.

Workup

  1. customReaction mixture
  2. distillationExcess solvent was distilled out
  3. additiondiluted with water
  4. filtrationPrecipitated product was filtered
  5. customto get crude product which
  6. customwas then recrystallized in EtOH

Sources & evidence

ORD record
ord-fda73789a06543ffb6085ce290ef4e22
Source dataset
uspto-grants-2016_07
Patent number
US09394300B2

Reaction notes

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