Ammonia → HCID 67816157, compound

HRID 1505469Notes

Reaction equation

HRID 1505469 reaction equation
P(Cl)(Cl)(Cl)=O.[F:6][C:7]1[C:36]([F:37])=[CH:35][CH:34]=[CH:33][C:8]=1[CH2:9][N:10]1[C:14]2=[N:15][CH:16]=[CH:17][CH:18]=[C:13]2[C:12]([C:19]2[N:20]=[N:21][C:22]([C:26]([CH3:32])([CH3:31])[C:27]([O:29]C)=O)=[C:23](O)[N:24]=2)=[N:11]1.[NH3:38]>C(#N)C>[F:6][C:7]1[C:36]([F:37])=[CH:35][CH:34]=[CH:33][C:8]=1[CH2:9][N:10]1[C:14]2=[N:15][CH:16]=[CH:17][CH:18]=[C:13]2[C:12]([C:19]2[N:20]=[N:21][C:22]3[C:26]([CH3:32])([CH3:31])[C:27](=[O:29])[NH:38][C:23]=3[N:24]=2)=[N:11]1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 24813Phosphorus oxychlorideHCID 178500129HCID 178500129, compound

Product 1

HCID 67816157HCID 67816157, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

8 ml of phosphoryl chloride were added to 0.75 g (1.703 mmol) of the compound from Example 75A, and the mixture was stirred at RT overnight. The reaction mixture was then taken up in 120 ml of acetonitrile and, with ice cooling, stirred into 72 ml of concentrated ammonia solution (33% in water). The reaction mixture was stirred at room temperature for 3 days and then concentrated on a rotary evaporator. The residue was stirred with water and ethyl acetate and the aqueous phase was extracted twice with ethyl acetate. The combined organic phases were washed with saturated aqueous sodium chloride solution and then dried over sodium sulphate, filtered and concentrated on a rotary evaporator. The residue was purified by preparative HPLC (acetonitrile/water/water+1% TFA—40:55:5). This gave 134 mg of the title compound (19% of theory).

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 3 days
  2. concentrationconcentrated on a rotary evaporator
  3. stirringThe residue was stirred with water and ethyl acetate
  4. extractionthe aqueous phase was extracted twice with ethyl acetate
  5. washThe combined organic phases were washed with saturated aqueous sodium chloride solution
  6. dry with materialdried over sodium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated on a rotary evaporator
  9. customThe residue was purified by preparative HPLC (acetonitrile/water/water+1% TFA—40:55:5)

Sources & evidence

ORD record
ord-89d09a28ab8842d5b0d9b47dc38d40de
Source dataset
uspto-grants-2015_12
Patent number
US09216978B2

Reaction notes

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