Trifluoroacetic acid → HCID 25097086, compound

HRID 1944355Notes

Reaction equation

HRID 1944355 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-84760428f58d41b99b9d5467da41bfb8
Source dataset
uspto-grants-2013_03
Patent number
US08394830B2

Reaction notes

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