Acetonitrile → HCID 68283437, compound

HRID 624033Notes

Reaction equation

HRID 624033 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][NH:7][CH:8]=1)([O-:3])=[O:2].Cl[CH2:10][C:11]([NH:13][C:14]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][N:15]=1)=[O:12].C([O-])([O-])=O.[Cs+].[Cs+].CC#N>C(Cl)Cl>[F:20][C:17]1[CH:18]=[CH:19][C:14]([NH:13][C:11](=[O:12])[CH2:10][N:6]2[CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:8]=[N:7]2)=[N:15][CH:16]=1

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 10796Cesium carbonateHCID 163764-nitro-1H-pyrazoleHCID 229347512-Chloro-N-(5-fluoro-2-pyridinyl)acetamide

Product 1

HCID 68283437HCID 68283437, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
80 °C

Procedure

A flask was charged with 4-nitro-1H-pyrazole (230 mg, 2.03 mmol), 2-chloro-N-(5-fluoropyridin-2-yl)acetamide (2.24 mmol), Cs2CO3 (729 g, 2.24 mmol) and MeCN (11.5 mL). The resulting reaction mixture was stirred at reflux (80° C.) for 2 h, then allowed to reach rt. The mixture was diluted with DCM, filtered, the filter cake was washed with DCM. The filtercake was redisolved in DCM and water, the org. layer was separated and the aq. layer was extracted with DCM (2×). The combined org. layers were washed with brine, dried (MgSO4), filtered and concentrated to yield N-(5-fluoropyridin-2-yl)-2-(4-nitro-1H-pyrazol-1-yl)acetamide as a crude which was used in the next step without further purification. LC-MS conditions A: tR=0.67 min, [M+H]+=266.32.

Workup

  1. customThe resulting reaction mixture
  2. customto reach rt
  3. filtrationfiltered
  4. washthe filter cake was washed with DCM
  5. customlayer was separated
  6. extractionthe aq. layer was extracted with DCM (2×)
  7. washlayers were washed with brine
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-7ecb42fd55c246a98eede5c3cc12ce2e
Source dataset
uspto-grants-2016_04
Patent number
US09303023B2

Reaction notes

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