Ethyl 4,4,4-trifluoro-2-methoxy-3-oxobutanoate → HCID 178493926, compound

HRID 537086Notes

Reaction equation

HRID 537086 reaction equation
F[C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[C:10]([NH2:13])[NH:11][N:12]=2)[CH:5]=[CH:6][CH:7]=1.C([O:16][C:17](=O)[CH:18]([O:25][CH3:26])[C:19](=[O:24])[C:20]([F:23])([F:22])[F:21])C>C(O)(=O)C>[OH:24][C:19]1([C:20]([F:21])([F:22])[F:23])[CH:18]([O:25][CH3:26])[C:17](=[O:16])[NH:13][C:10]2[NH:11][N:12]=[C:8]([C:4]3[CH:5]=[CH:6][CH:7]=[CH:2][CH:3]=3)[C:9]1=2

Participants

4

Reactant 2

HCID 2758936Ethyl 4,4,4-trifluoro-2-methoxy-3-oxobutanoateHCID 178507283HCID 178507283, compound

Product 1

HCID 178493926HCID 178493926, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

5-Phenyl-2H-pyrazol-3-ylamine (i) (100 mg, 0.62 mmol) was dissolved in glacial acetic acid (1 mL), 4,4,4-Trifluoro-2-methoxy-3-oxo-butyric acid ethyl ester (95%, 0.17 mL, 0.92 mmol) was added at RT and stirring was continued for 15 h at 120° C. The mixture was evaporated to dryness and the isomeric mixture was directly purified by preparative HPLC (Agilent 1100 Series, Chromolith prep RP-18e, 100-25). A colorless solid (92 mg, 0.28 mmol, 46%) was obtained, characterized as compound (x).

Workup

  1. customThe mixture was evaporated to dryness
  2. customthe isomeric mixture was directly purified by preparative HPLC (Agilent 1100 Series, Chromolith prep RP-18e, 100-25)

Sources & evidence

ORD record
ord-dbad08d26df8460d9eeb16ad13fe6f4a
Source dataset
uspto-grants-2014_10
Patent number
US08859775B2

Reaction notes

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