Water → HCID 9841847, compound

HRID 1060586Notes

Reaction equation

HRID 1060586 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].Cl[C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([O:16][CH3:17])[CH:14]=2)[C:9]([CH2:18][C:19]2[C:24]([Cl:25])=[CH:23][N:22]=[CH:21][C:20]=2[Cl:26])=[N:8][N:7]=1.O>CN(C=O)C>[Cl:25][C:24]1[CH:23]=[N:22][CH:21]=[C:20]([Cl:26])[C:19]=1[CH2:18][C:9]1[C:10]2[C:15](=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)[C:6]2=[N:7][N:8]=[N:3][N:2]2[N:1]=1

Participants

5

Reactant 3

HCID 962WaterHCID 33557Sodium AzideHCID 186292104-Chloro-1-[(3,5-dichloropyridin-4-yl)methyl]-6-methoxyphthalazine

Product 1

HCID 9841847HCID 9841847, compoundYield 78.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

NaN3 was added to a solution under N2 of 4-chloro-1-(3,5-dichloro-pyridin4-ylmethyl)-6-methoxy-phthalazine (1 g, 2.82 mmoles), obtained as described in example 13, in anhydrous DMF (20 ml) and the mixture was heated at 80° C. overnight, then at 120° C. for 7 hours, then poured into water (10 volumes) and extracted 3 times with CH2Cl2, dried and concentrated under vacuum to give a solid which was purified by flash chromatography (eluent:60:80 petrolatum/ethyl acetate 6:4). The eluate was crystallised from acetonitrile (75 ml) to give 0.36 g of the title compound (yield: 78.5%). m. p.: 275-276° C.

Workup

  1. customobtained
  2. extractionextracted 3 times with CH2Cl2
  3. customdried
  4. concentrationconcentrated under vacuum
  5. customto give a solid which
  6. customwas purified by flash chromatography (eluent:60:80 petrolatum/ethyl acetate 6:4)
  7. customThe eluate was crystallised from acetonitrile (75 ml)

Sources & evidence

ORD record
ord-d046450e286649eea61705da68891668
Source dataset
uspto-grants-2003_02
Patent number
US06525055B1

Reaction notes

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