Acetate → HCID 9949395, compound

HRID 49867Notes

Reaction equation

HRID 49867 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([CH2:12][C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)=[N:4][N:3]=1.[F:19][C:20]1[CH:26]=[CH:25][C:23]([NH2:24])=[CH:22][CH:21]=1.C([O-])(=O)C.C(=O)([O-])[O-].[K+].[K+]>>[F:19][C:20]1[CH:26]=[CH:25][C:23]([NH:24][C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]([CH2:12][C:13]3[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=3)=[N:4][N:3]=2)=[CH:22][CH:21]=1

Participants

5

Reactant 4

HCID 175AcetateHCID 97314-FluoroanilineHCID 11430Potassium CarbonateHCID 19446091-Chloro-4-(4-pyridinylmethyl)phthalazine

Product 1

HCID 9949395HCID 9949395, compound

Conditions

Temperature
90 °C

Procedure

A mixture of 0.511 g (2 mmol) 1-chloro-4-(4-pyridylmethyl)phthalazine and 0.576 ml (6 mmol) 4-fluoroaniline is heated for 2 h at 90° C. The residue is then distributed between acetate and 20% aqueous potassium carbonate solution. The organic phase washed with water and dried over sodium sulfate is evaporated and the residue purified on silica gel by flash chromatography using acetate/methanol mixtures (50:1 and 25:1). Title compound is obtained after crystallization of the product-containing fractions from acetonitrile and drying under HV (6 h, 100° C.); m.p. 129-131° C.; ESI-MS: (M+H)+=331.

Workup

  1. washThe organic phase washed with water
  2. dry with materialdried over sodium sulfate
  3. customis evaporated
  4. customthe residue purified on silica gel by flash chromatography

Sources & evidence

ORD record
ord-ac39a0f1f7a347668c01e5f18e9de5ef
Source dataset
uspto-grants-2004_03
Patent number
US06710047B2

Reaction notes

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