Nitrogen → 1-[4-(3,5-Dichloro-pyridin-4-ylmethyl)-7-methoxy-1H-phthalazin-2-yl]-ethanone

HRID 2297415Notes

Reaction equation

HRID 2297415 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:21])[C:7]=1[CH2:8][C:9]1[C:18]2[C:13](=[CH:14][C:15]([O:19][CH3:20])=[CH:16][CH:17]=2)[CH2:12][NH:11][N:10]=1.N#N.C(N(CC)CC)C.[C:31](Cl)(=[O:33])[CH3:32]>C1COCC1>[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:21])[C:7]=1[CH2:8][C:9]1[C:18]2[C:13](=[CH:14][C:15]([O:19][CH3:20])=[CH:16][CH:17]=2)[CH2:12][N:11]([C:31](=[O:33])[CH3:32])[N:10]=1

Participants

6

Reactant 4

HCID 947NitrogenHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 9797215Phthalazine, 4-[(3,5-dichloro-4-pyridinyl)methyl]-1,2-dihydro-7-methoxy-

Product 1

HCID 183816741-[4-(3,5-Dichloro-pyridin-4-ylmethyl)-7-methoxy-1H-phthalazin-2-yl]-ethanoneYield 86.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

As an alternative to the previous synthesis, the title compound was prepared starting from a solution of 4-(3,5-dichloro-pyridin-4-ylmethyl)-7-methoxy-1,2-dihydro-phthalazine (2 g, 6.2 mmoles), prepared as described in example 22, in dry THF (60 ml) under stirring and dry N2 at 0° C. The mixture was added with triethylamine (1.57 g, 15.5 mmoles), then with acetyl chloride (0.44 ml, 6.2 mmoles). After 10 minutes the mixture was brought to room temperature and kept at such temperature for 2.5 hours, then poured into water/ice and extracted more times with CH2Cl2. The organic phases were washed with 5% NaOH and water, anhydrified and brought to dryness to give a solid which, by crystallisation from acetonitrile (70 ml), gave 1.95 g of the title compound having the same physochemical characteristics set forth at point A.

Workup

  1. customAs an alternative to the previous synthesis
  2. customthe title compound was prepared
  3. customprepared
  4. customat 0° C
  5. waitkept at such temperature for 2.5 hours
  6. extractionextracted more times with CH2Cl2
  7. washThe organic phases were washed with 5% NaOH and water
  8. customto give a solid which
  9. customby crystallisation from acetonitrile (70 ml)

Sources & evidence

ORD record
ord-42e5be27e4b347b7a2fbe1e1069599d5
Source dataset
uspto-grants-2002_12
Patent number
US06492360B1

Reaction notes

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