Ammonium Hydroxide → HCID 58779347, compound

HRID 1372481Notes

Reaction equation

HRID 1372481 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]([NH:5][NH:6][C:7]1[CH:12]=[CH:11][C:10]([I:13])=[CH:9][N:8]=1)=O.[OH-].[NH4+]>OP(O)(O)=O>[I:13][C:10]1[CH:11]=[CH:12][C:7]2[N:8]([C:3]([C:2]([F:15])([F:14])[F:1])=[N:5][N:6]=2)[CH:9]=1

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 21071710HCID 21071710, compound

Product 1

HCID 58779347HCID 58779347, compound

Reagents, catalysts & solvents 1

HCID 1004Phosphoric AcidSolvent

Conditions

Temperature
140 °C

Procedure

The product (145 mg, 0.438 mmol) from Step A was suspended in superphosphoric acid (5 mL), and the mixture was heated at 140° C. for 6 h. The mixture was allowed to cool to room temperature, poured into ice, and neutralized with concentrated aqueous ammonium hydroxide solution. The mixture was extracted several times with ethyl acetate, and the combined extracts were washed with saturated aqueous brine, dried (magnesium sulfate), and concentrated under reduced pressure. The resultant residue was purified by preparative thin layer chromatography (silica, 8% methanol/dichloromethane) to afford the title compound. LC/MS 313.8 (M+1).

Workup

  1. temperatureto cool to room temperature
  2. additionpoured into ice
  3. extractionThe mixture was extracted several times with ethyl acetate
  4. washthe combined extracts were washed with saturated aqueous brine
  5. dry with materialdried (magnesium sulfate)
  6. concentrationconcentrated under reduced pressure
  7. customThe resultant residue was purified by preparative thin layer chromatography (silica, 8% methanol/dichloromethane)

Sources & evidence

ORD record
ord-2b39e46a5137468aad2251131a7cda9c
Source dataset
uspto-grants-2007_01
Patent number
US07157490B2

Reaction notes

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