Trifluoroacetic acid → 2-((2-Carbamoyl-6-(trifluoromethyl)quinolin-4-yl)amino)acetic acid

HRID 1896881Notes

Reaction equation

HRID 1896881 reaction equation
[C:1]([C:4]1[CH:13]=[C:12]([NH:14][CH2:15][C:16]([O:18]C(C)(C)C)=[O:17])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:23]([F:26])([F:25])[F:24])[CH:10]=2)[N:5]=1)(=[O:3])[NH2:2].C1(SC)C=CC=CC=1.FC(F)(F)C(O)=O>C(Cl)Cl.CCOCC>[C:1]([C:4]1[CH:13]=[C:12]([NH:14][CH2:15][C:16]([OH:18])=[O:17])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:23]([F:24])([F:25])[F:26])[CH:10]=2)[N:5]=1)(=[O:3])[NH2:2]

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7520ThioanisoleHCID 68003428Tert-butyl 2-((2-carbamoyl-6-(trifluoromethyl)quinolin-4-yl)amino)acetate

Product 1

HCID 585626142-((2-Carbamoyl-6-(trifluoromethyl)quinolin-4-yl)amino)acetic acid

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl 2-((2-carbamoyl-6-(trifluoromethyl)quinolin-4-yl)amino)acetate (200 mg, 0.54 mmol) above step B, in DCM (5 mL) was treated with thioanisole (0.05 mL) and stirred for 10 min and then treated with trifluoroacetic acid (5 mL) dropwise. The resulting opaque solution was stirred for 2.5 h at room temperature and diluted with Et2O (200 mL). Precipitate was formed. The solid was dried under high vacuum to give the title compound.

Workup

  1. stirringThe resulting opaque solution was stirred for 2.5 h at room temperature
  2. customPrecipitate was formed
  3. customThe solid was dried under high vacuum

Sources & evidence

ORD record
ord-4b433ac0b88a44a5af11061ce25b4287
Source dataset
uspto-grants-2013_08
Patent number
US08518969B2

Reaction notes

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