Ammonia → HCID 22386466, compound

HRID 2119319Notes

Reaction equation

HRID 2119319 reaction equation
[CH3:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13](=O)[NH:12][N:11]=2)=[CH:4][CH:3]=1.P(Cl)(Cl)([Cl:23])=O.Cl.N>C(#N)C.O1CCOCC1.O>[Cl:23][C:13]1[C:14]2[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:10]([CH2:9][CH2:8][C:5]2[CH:6]=[N:7][C:2]([CH3:1])=[CH:3][CH:4]=2)=[N:11][N:12]=1

Participants

8

Reactant 4

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 24813Phosphorus oxychlorideHCID 22386451HCID 22386451, compound

Product 1

HCID 22386466HCID 22386466, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

Under N2-atmosphere, 217 mg (0.818 mmol) 4-[2-(6-methylpyridin-3-yl)ethyl]phthalazin-1(2H)-one in 3.3 ml acetonitrile is mixed with 187 μl (2.04 mmol) phosphoryl chloride and 0.41 ml 4 N HCl in dioxane and stirred for 9 h at 60° C. After cooling to RT, 2.6 ml H2O, followed by a solution of 0.5 ml sat. NH3 and 5 ml H2O is added. Immediate extraction with 3 portions of EtOAc, washing of the organic layers with water and brine, drying (Na2SO4) and evaporation yield the title compound; FAB-MS (M+H)+=284.

Workup

  1. temperatureAfter cooling to RT
  2. additionis added
  3. extractionImmediate extraction with 3 portions of EtOAc
  4. washwashing of the organic layers with water and brine
  5. customdrying
  6. custom(Na2SO4) and evaporation

Sources & evidence

ORD record
ord-c7c125d168494162b71a15e7fba9d342
Source dataset
uspto-grants-2004_02
Patent number
US06686347B2

Reaction notes

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