Phosphorus oxychloride → HCID 18393037, compound

HRID 1739419Notes

Reaction equation

HRID 1739419 reaction equation
[C:1]([O:4][CH2:5][C@@H:6]([NH:18][C:19](=O)[C:20]1[CH:25]=[CH:24][N:23]=[C:22]([N:26]2[N:35]=[C:34]([C:36]3[CH:37]=[N:38][CH:39]=[CH:40][CH:41]=3)[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[C:27]2=[O:42])[CH:21]=1)[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[C:10]([O:16][CH3:17])[CH:9]=1)(=[O:3])[CH3:2].P(Cl)(Cl)(Cl)=O.C(=O)([O-])O.[Na+]>C(#N)C>[C:1]([O:4][CH2:5][C@@H:6]1[CH2:7][C:8]2[C:13](=[CH:12][C:11]([O:14][CH3:15])=[C:10]([O:16][CH3:17])[CH:9]=2)[C:19]([C:20]2[CH:25]=[CH:24][N:23]=[C:22]([N:26]3[N:35]=[C:34]([C:36]4[CH:37]=[N:38][CH:39]=[CH:40][CH:41]=4)[C:33]4[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=4)[C:27]3=[O:42])[CH:21]=2)=[N:18]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 18393033HCID 18393033, compound

Product 1

HCID 18393037HCID 18393037, compoundYield 93.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of (2S)-1-acetoxy-3-(3,4-dimethoxyphenyl)-2-{2-[4-(3-pyridyl)phthalazin-1(2H)-on-2-yl]isonicotinoylamino}propane (150 mg) in acetonitrile (5 ml) is added phosphorus oxychloride (0.29 ml), and the mixture is heated under reflux overnight. The reaction mixture is cooled to room temperature, and neutralized with an aqueous sodium hydrogen carbonate solution. The mixture is extracted with chloroform, and the extract is washed, dried, and concentrated. The residue is crystallized from ethyl acetate to give (3S)-4-(3-acetoxymethyl-3,4-dihydro-6,7-dimethoxyisoquinolin-1-yl)-2-[4-(3-pyridyl)phthalazin-1(2H)-on-2-yl]pyridine (136 mg), as yellow crystals.

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux overnight
  3. extractionThe mixture is extracted with chloroform
  4. washthe extract is washed
  5. customdried
  6. concentrationconcentrated
  7. customThe residue is crystallized from ethyl acetate

Sources & evidence

ORD record
ord-2cd483b238314dac9cd756c65c16331a
Source dataset
uspto-grants-1999_10
Patent number
US05965730

Reaction notes

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