Trifluoroacetic acid → HCID 25097086, compound

HRID 1922141Notes

Reaction equation

HRID 1922141 reaction equation
C([O:5][C:6](=[O:40])[CH2:7][O:8][C:9]1[CH:18]=[CH:17][C:16]([Cl:19])=[C:15]2[C:10]=1[C:11]([CH3:39])=[C:12]([CH2:24][C:25]1[CH:30]=[CH:29][C:28]([N:31]3[CH:35]=[CH:34][C:33]([CH:36]4[CH2:38][CH2:37]4)=[N:32]3)=[CH:27][CH:26]=1)[C:13]([O:20][CH:21]([F:23])[F:22])=[N:14]2)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[Cl:19][C:16]1[CH:17]=[CH:18][C:9]([O:8][CH2:7][C:6]([OH:40])=[O:5])=[C:10]2[C:15]=1[N:14]=[C:13]([O:20][CH:21]([F:22])[F:23])[C:12]([CH2:24][C:25]1[CH:26]=[CH:27][C:28]([N:31]3[CH:35]=[CH:34][C:33]([CH:36]4[CH2:37][CH2:38]4)=[N:32]3)=[CH:29][CH:30]=1)=[C:11]2[CH3:39]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67458121HCID 67458121, compound

Product 1

HCID 25097086HCID 25097086, compoundYield 34.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of {8-chloro-3-[4-(3-cyclopropylpyrazol-1-yl)benzyl]-2-difluoromethoxy-4-methylquinolin-5-yloxy}acetic acid tert-butyl ester (0.11 g) in dichloromethane (8.0 mL) was treated with trifluoroacetic acid (2.0 mL), and the resulting mixture was stirred at room temperature for 5 hours. The mixture was concentrated under reduced pressure, diluted with saturated aqueous sodium acetate solution and then extracted with ethyl acetate. The combined extracts were dried over magnesium sulphate and then concentrated under reduced pressure to afford the title compound as a white solid (0.034 g).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. additiondiluted with saturated aqueous sodium acetate solution
  3. extractionextracted with ethyl acetate
  4. dry with materialThe combined extracts were dried over magnesium sulphate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-728ed2de470845e081d58df3fcd1591a
Source dataset
uspto-grants-2012_05
Patent number
US08173812B2

Reaction notes

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