3-Methyl-5-isoxazolecarboxylic acid → 3-(6-Chloro-[1,2,4]triazolo[3,4-a]phthalazin-3-yl)-5-methylisoxazole

Reaction equation

[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([NH:12][NH2:13])=[N:4][N:3]=1.[CH3:14][C:15]1[O:19][N:18]=[C:17]([C:20](O)=O)[CH:16]=1>>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]2=[N:12][N:13]=[C:20]([C:17]3[CH:16]=[C:15]([CH3:14])[O:19][N:18]=3)[N:4]2[N:3]=1

Participants

Reactant 2

HCID 769473-Methyl-5-isoxazolecarboxylic acid

HCID 27937521-Chloro-4-hydrazinophthalazine

Product 1

HCID 184275393-(6-Chloro-[1,2,4]triazolo[3,4-a]phthalazin-3-yl)-5-methylisoxazole

Procedure

Intermediate 14b was prepared in two steps from intermediate 11 in an analogous fashion to the preparation of intermediate 14a (see Example 1). Commercially available 5-methylisoxazole-3-carboxylic acid (12c) was used in the first step.

Sources & evidence

ORD record: ord-f3d7ee1e86bb4017898ed1eb00956112
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08557815B2

Reaction notes

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