Imidazole → HCID 18381680, compound

HRID 2268888Notes

Reaction equation

HRID 2268888 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.[H-].[Na+].Cl[C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([O:19][CH3:20])[CH:17]=2)[C:12]([CH2:21][C:22]2[C:27]([Cl:28])=[CH:26][N:25]=[CH:24][C:23]=2[Cl:29])=[N:11][N:10]=1>CN(C=O)C>[Cl:29][C:23]1[CH:24]=[N:25][CH:26]=[C:27]([Cl:28])[C:22]=1[CH2:21][C:12]1[C:13]2[C:18](=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)[C:9]([N:1]2[CH:5]=[CH:4][N:3]=[CH:2]2)=[N:10][N:11]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 24758Sodium hydrideHCID 186292104-Chloro-1-[(3,5-dichloropyridin-4-yl)methyl]-6-methoxyphthalazine

Product 1

HCID 18381680HCID 18381680, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
80 °C

Procedure

A solution of imidazole (0.814 g, 11.21 mmoles) in dry DMF (30 ml) was stirred under N2 at room temperature and added with NaH (8.46 mmoles). After 30 minutes 4-chloro-1-(3,5-dichloro-pyridin-4-ylmethyl)-6-methoxy-phthalazine (2 g, 5.64 mmoles), prepared as described in example 45, in dry DMF (30 ml) was added. The mixture was heated at 80° C. 5 for 3.5 hours, cooled, poured into water/ice and extracted three times with CH2Cl2. The organic phase was washed with water, anhydrified and concentrated to give a solid which was flash chromatographed (eluent: ethyl acetate) yielding 0.9 g of the title compound (yield: 50%). m.p.>250° C.

Workup

  1. customprepared
  2. additionwas added
  3. temperaturecooled
  4. extractionextracted three times with CH2Cl2
  5. washThe organic phase was washed with water, anhydrified
  6. concentrationconcentrated
  7. customto give a solid which
  8. customchromatographed (eluent: ethyl acetate)

Sources & evidence

ORD record
ord-94f6515adf4043a094c8e9b6e2b6800d
Source dataset
uspto-grants-2001_12
Patent number
US06329370B1

Reaction notes

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