Ammonia → HCID 18440623, compound

HRID 457703Notes

Reaction equation

HRID 457703 reaction equation
[Cl:1][C:2]1[N:3]=[C:4](Cl)[C:5]2[CH:11]=[C:10]([O:12][C:13]3[CH:18]=[CH:17][C:16]([F:19])=[CH:15][C:14]=3[F:20])[N:9]=[CH:8][C:6]=2[N:7]=1.[NH3:22]>CO>[Cl:1][C:2]1[N:3]=[C:4]([NH2:22])[C:5]2[CH:11]=[C:10]([O:12][C:13]3[CH:18]=[CH:17][C:16]([F:19])=[CH:15][C:14]=3[F:20])[N:9]=[CH:8][C:6]=2[N:7]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 18440621HCID 18440621, compound

Product 1

HCID 18440623HCID 18440623, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Compound (1E) (1.75 g, 5.33 mmol) was placed in a sealed-tube, and 7 N ammonia in MeOH (Aldrich Chemical Co.) (30 mL) was added. The tube was tightly capped, and the resulting homogeneous mixture was stirred at room temperature overnight. The next morning, TLC confirmed that the reaction was complete. The mixture was transferred to a round-bottom flask and concentrated under reduced pressure at 55° C. The residue was taken up in EtOAc (700 mL) and water (250 mL). The layers were partitioned and then separated. The organic layer was washed with water (2×250 mL) and brine (1×250 mL). The organic layer was dried over magnesium sulfate, filtered, concentrated, and pumped to give the title compound (1F) as an off-white powder (1.859 g, (M−H)−=307, Mp>300° C.).

Workup

  1. customThe tube was tightly capped
  2. customThe mixture was transferred to a round-bottom flask
  3. concentrationconcentrated under reduced pressure at 55° C
  4. customThe layers were partitioned
  5. customseparated
  6. washThe organic layer was washed with water (2×250 mL) and brine (1×250 mL)
  7. dry with materialThe organic layer was dried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-02e93f47571a446cbc47c87761b46382
Source dataset
uspto-grants-2007_03
Patent number
US07189731B2

Reaction notes

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