Ethyl 4,4,4-trifluoroacetoacetate → 4-Hydroxy-1-methyl-3-phenyl-4-trifluoromethyl-1,4,5,7-tetrahydro-pyrazolo[3,4-b]pyridin-6-one

HRID 537085

Reaction equation

HRID 537085 reaction equation
[CH3:1][N:2]1[C:6]([NH2:7])=[CH:5][C:4]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[N:3]1.C([O:16][C:17](=O)[CH2:18][C:19]([C:21]([F:24])([F:23])[F:22])=[O:20])C>C(O)(=O)C>[OH:20][C:19]1([C:21]([F:24])([F:23])[F:22])[CH2:18][C:17](=[O:16])[NH:7][C:6]2[N:2]([CH3:1])[N:3]=[C:4]([C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=3)[C:5]1=2

Participants

4

Reactant 2

HCID 67793Ethyl 4,4,4-trifluoroacetoacetateHCID 5177791-Methyl-3-phenyl-1H-pyrazol-5-amine

Product 1

HCID 1360703454-Hydroxy-1-methyl-3-phenyl-4-trifluoromethyl-1,4,5,7-tetrahydro-pyrazolo[3,4-b]pyridin-6-oneYield 16%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

2-Methyl-5-phenyl-2H-pyrazol-3-ylamine (vii) (100 mg, 0.58 mmol) was dissolved in glacial acetic acid (1 mL), ethyl-4,4,4-trifluoracetoacetate (0.13 mL, 0.85 mmol) was added at RT and stirring was continued for 2.5 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 (29 mg, 0.09 mmol, 16%) was obtained, characterized as compound (viii).

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-ecfb0a05e42b4c9d8073851ecb792eff
Source dataset
uspto-grants-2014_10
Patent number
US08859775B2

Linked notes

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