Sodium 3-ethoxy-2-fluoro-3-oxoprop-1-en-1-olate → HCID 178517415, compound

HRID 2281923Notes

Reaction equation

HRID 2281923 reaction equation
[F:1][C:2]1[C:21](F)=[CH:20][CH:19]=[CH:18][C:3]=1[CH2:4][N:5]1[C:9]([C:10]2[CH:14]=[CH:13][O:12][N:11]=2)=[CH:8][C:7]([C:15](=[NH:17])[NH2:16])=[N:6]1.C([O:25][C:26](=O)[C:27]([F:30])=[CH:28][O-])C.[Na+]>C(O)C>[F:30][C:27]1[C:26]([OH:25])=[N:16][C:15]([C:7]2[CH:8]=[C:9]([C:10]3[CH:14]=[CH:13][O:12][N:11]=3)[N:5]([CH2:4][C:3]3[CH:18]=[CH:19][CH:20]=[CH:21][C:2]=3[F:1])[N:6]=2)=[N:17][CH:28]=1

Participants

4

Reactant 2

HCID 71435423Sodium 3-ethoxy-2-fluoro-3-oxoprop-1-en-1-olateHCID 896567921-(2,3-difluorobenzyl)-5-(isoxazol-3-yl)-1H-pyrazole-3-carboximidamide

Product 1

HCID 178517415HCID 178517415, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

This was generated via the cyclization of known intermediate 1-(2,3-difluorobenzyl)-5-(isoxazol-3-yl)-1H-pyrazole-3-carboximidamide (213 mg, 0.702 mmol) with sodium 3-ethoxy-2-fluoro-3-oxoprop-1-en-1-olate (440 mg, 2.81 mmol) in ethanol (5.0 mL)—stirring at 90° C. for 14 hour. The solvent was removed in vacuo, and purification by silica gel chromatography (0-10% methanol in DCM) provided a mixture of the desired compound and a side-product. The mixture was then subjected to reverse-phase preparative HPLC which afforded Compound 93 (15 mg, 7.2% yield) as a white solid.

Workup

  1. customThe solvent was removed in vacuo, and purification by silica gel chromatography (0-10% methanol in DCM)
  2. customprovided

Sources & evidence

ORD record
ord-d68828b3215b4c8b91ea049e50fb5f80
Source dataset
uspto-grants-2015_09
Patent number
US09139564B2

Reaction notes

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