Ammonia → HCID 66574956, compound

HRID 1529172Notes

Reaction equation

HRID 1529172 reaction equation
P(Cl)(Cl)(Cl)=O.O[C:7]1[N:8]=[C:9]([C:20]2[C:28]3[C:23](=[N:24][CH:25]=[CH:26][CH:27]=3)[N:22]([CH2:29][CH2:30][C:31]([F:37])([F:36])[C:32]([F:35])([F:34])[F:33])[N:21]=2)[N:10]=[N:11][C:12]=1[C:13]([CH3:19])([CH3:18])[C:14]([O:16]C)=O.[NH3:38]>C(#N)C>[CH3:19][C:13]1([CH3:18])[C:12]2[N:11]=[N:10][C:9]([C:20]3[C:28]4[C:23](=[N:24][CH:25]=[CH:26][CH:27]=4)[N:22]([CH2:29][CH2:30][C:31]([F:37])([F:36])[C:32]([F:34])([F:35])[F:33])[N:21]=3)=[N:8][C:7]=2[NH:38][C:14]1=[O:16]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 24813Phosphorus oxychlorideHCID 178500134HCID 178500134, compound

Product 1

HCID 66574956HCID 66574956, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4 ml of phosphoryl chloride were added to 263 mg (0.571 mmol) of the compound from Example 16A, and the mixture was stirred at RT overnight. The reaction mixture was dissolved in 38 ml of acetonitrile and, with ice-cooling, stirred into 24 ml of concentrated aqueous ammonia solution (33% strength). The mixture was stirred at RT for 2 days. The reaction mixture was then concentrated. The residue was taken up in water and ethanol and stirred at RT for 1 h. The precipitate formed was filtered off with suction and washed with water and ethanol. This residue was purified by preparative HPLC (acetonitrile:water (+0.05% formic acid) gradient). This gave 119 mg of the title compound (49% of theory).

Workup

  1. temperaturecooling
  2. stirringThe mixture was stirred at RT for 2 days
  3. concentrationThe reaction mixture was then concentrated
  4. stirringethanol and stirred at RT for 1 h
  5. customThe precipitate formed
  6. filtrationwas filtered off with suction
  7. washwashed with water and ethanol
  8. customThis residue was purified by preparative HPLC (acetonitrile:water (+0.05% formic acid) gradient)

Sources & evidence

ORD record
ord-a8c26560717340c8b2dfefba16cd384b
Source dataset
uspto-grants-2015_07
Patent number
US09090610B2

Reaction notes

Loading…