1H-1,2,4-Triazole → 1-(3,5-Dichloro-pyridin-4-ylmethyl)-6-difluoromethoxy-4-[1,2,4]triazol-1-yl-phthalazine

HRID 2268901Notes

Reaction equation

HRID 2268901 reaction equation
[NH:1]1[CH:5]=[N:4][CH:3]=[N:2]1.[H-].[Na+].Cl[C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([O:19][CH:20]([F:22])[F:21])[CH:17]=2)[C:12]([CH2:23][C:24]2[C:29]([Cl:30])=[CH:28][N:27]=[CH:26][C:25]=2[Cl:31])=[N:11][N:10]=1>CN(C=O)C>[Cl:31][C:25]1[CH:26]=[N:27][CH:28]=[C:29]([Cl:30])[C:24]=1[CH2:23][C:12]1[C:13]2[C:18](=[CH:17][C:16]([O:19][CH:20]([F:21])[F:22])=[CH:15][CH:14]=2)[C:9]([N:1]2[CH:5]=[N:4][CH:3]=[N:2]2)=[N:10][N:11]=1

Participants

5

Reactant 3

HCID 92571H-1,2,4-TriazoleHCID 24758Sodium hydrideHCID 183816244-Chloro-1-(3,5-dichloro-pyridin-4-ylmethyl)-6-difluoromethoxy-phthalazine

Product 1

HCID 183816471-(3,5-Dichloro-pyridin-4-ylmethyl)-6-difluoromethoxy-4-[1,2,4]triazol-1-yl-phthalazineYield 56.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution under N2 of 1,2,4-triazole (2.4 g, 34.8 mmoles) in DMF (100 ml) was added with NaH (1.05 g, 26.1 mmoles). The mixture was stirred at room temperature up to clarity, then added with 4-chloro-1-(3,5-dichloro-pyridin-4-ylmethyl)-6-difluoromethoxy-phthalazine (6.8 g, 17.4 mmoles), prepared as described in example 99. The mixture was heated at 100° C. for 5 hours, extracted three times with CH2Cl2. The organic phase was anhydrified and dried to give a solid which was flash chromatographed (eluent: ethyl acetate/petrolatum 7:3 to 100% of ethyl acetate) to give 4.14 g of the title compound (yield: 28%). m.p.: 220-224° C.

Workup

  1. customprepared
  2. temperatureThe mixture was heated at 100° C. for 5 hours
  3. extractionextracted three times with CH2Cl2
  4. customdried
  5. customto give a solid which
  6. customchromatographed (eluent: ethyl acetate/petrolatum 7:3 to 100% of ethyl acetate)

Sources & evidence

ORD record
ord-0c0227ef8910406695c1f8409ecf6a98
Source dataset
uspto-grants-2001_12
Patent number
US06329370B1

Reaction notes

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