Hydrochloric Acid → HCID 68282941, compound

HRID 624034Notes

Reaction equation

HRID 624034 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=O)[CH2:10][N:11]2[CH:15]=[C:14]([N+:16]([O-:18])=[O:17])[CH:13]=[N:12]2)=[N:6][CH:7]=1.Cl>C1COCC1.CCOC(C)=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][CH2:9][CH2:10][N:11]2[CH:15]=[C:14]([N+:16]([O-:18])=[O:17])[CH:13]=[N:12]2)=[N:6][CH:7]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 68283437HCID 68283437, compound

Product 1

HCID 68282941HCID 68282941, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent3×HCID 8857Ethyl AcetateSolvent

Procedure

To N-(5-fluoropyridin-2-yl)-2-(4-nitro-1H-pyrazol-1-yl)acetamide (493 mg) in THF (2.0 mL), BH3 THF-complex solution (1 M in THF, 7.3 mL, 7.3 mmol) was added dropwise. After stirring at rt for 3 h, the reaction mixture was quenched with 1 N aq. HCl-solution (3 mL, 3 mmol). The mixture was stirred for 15 min at rt, and heated to 60° C. for 1.5 h. The reaction mixture was diluted with EtOAc, washed with sat. aq. Na2CO3-solution. The aq. layer was reextracted with EtOAc and the comb. org. layers were evaporated, dissolved in DCM and washed with brine. The org. layer was dried (MgSO4), filtered and the solvent was removed by reduced pressure to yield 5-fluoro-N-(2-(4-nitro-1H-pyrazol-1-yl)ethyl)pyridin-2-amine as a yellow solid. LC-MS conditions A: tR=0.53 min, [M+H]+=252.36.

Workup

  1. stirringThe mixture was stirred for 15 min at rt
  2. temperatureheated to 60° C. for 1.5 h
  3. washwashed with sat. aq. Na2CO3-solution
  4. customlayers were evaporated
  5. dissolutiondissolved in DCM
  6. washwashed with brine
  7. dry with materiallayer was dried (MgSO4)
  8. filtrationfiltered
  9. customthe solvent was removed by reduced pressure

Sources & evidence

ORD record
ord-09856ca05786485782ea34783f9f5fd1
Source dataset
uspto-grants-2016_04
Patent number
US09303023B2

Reaction notes

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