2,6-Difluorobenzhydrazide → 7-(2,6-Difluorophenyl)-3-(2-fluorophenyl)-2-(2-methyl-2H-[1,2,4]triazol-3-ylmethoxy)pyrazolo[1,5-d][1,2,4]triazine

HRID 1016409

Reaction equation

HRID 1016409 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:9]([O:24][CH2:25][C:26]2[N:27]([CH3:31])[N:28]=[CH:29][N:30]=2)=[N:10][N:11]2[C:16]=1[CH:15]=[N:14][N:13]=[C:12]2[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[F:23].[F:32]C1C=CC=C(F)C=1C(NN)=O>>[F:23][C:18]1[CH:19]=[CH:20][CH:21]=[C:22]([F:32])[C:17]=1[C:12]1[N:11]2[N:10]=[C:9]([O:24][CH2:25][C:26]3[N:27]([CH3:31])[N:28]=[CH:29][N:30]=3)[C:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[F:1])=[C:16]2[CH:15]=[N:14][N:13]=1

Participants

3

Reactant 2

HCID 6764492,6-DifluorobenzhydrazideHCID 98883153,7-bis(2-fluorophenyl)-2-((2-methyl-2H-1,2,4-triazol-3-yl)methoxy)pyrazolo[1,5-d][1,2,4]triazine

Product 1

HCID 184069057-(2,6-Difluorophenyl)-3-(2-fluorophenyl)-2-(2-methyl-2H-[1,2,4]triazol-3-ylmethoxy)pyrazolo[1,5-d][1,2,4]triazine

Procedure

This compound was prepared using the procedure described in Example 21, steps b) to f), using 3-(2-fluorophenyl)-4-hydroxy-2-furanone (cf Example 2) instead of 3-tert-butyl-4-hydroxy-2-furanone and 2,6-difluorobenzoic hydrazide instead of 2,5-difluorobenzoic hydrazide in step e). Data for the title compound: mp=163° C.; 1H NMR (360 MHz, CDCl3) δ 3.78 (3H, s), 5.52 (2H, s), 7.16 (2H, m), 7.24-7.29 (2H, m), 7.38-7.44 (1H, m), 7.60-7.65 (2H, m), 7.85 (1H, s), 9.31 (1H, s); MS (ES+) m/e 438 [MH]+.

Workup

  1. customThis compound was prepared

Sources & evidence

ORD record
ord-9facc743d1db4ef48929729eb798aff9
Source dataset
uspto-grants-2002_11
Patent number
US06476030B1

Linked notes

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