Benzeneacetic acid, hydrazide → 3-Benzyl-6-thiophen-2-yl-[1,2,4]triazolo[4,3-b]pyridazine

HRID 1661795Notes

Reaction equation

HRID 1661795 reaction equation
[C:1]1([CH2:7][C:8]([NH:10][NH2:11])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[C:13]1[N:14]=[N:15][C:16]([C:19]2[S:20][CH:21]=[CH:22][CH:23]=2)=[CH:17][CH:18]=1>>[CH2:7]([C:8]1[N:14]2[N:15]=[C:16]([C:19]3[S:20][CH:21]=[CH:22][CH:23]=3)[CH:17]=[CH:18][C:13]2=[N:11][N:10]=1)[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 2

HCID 70301Benzeneacetic acid, hydrazideHCID 64047013-Chloro-6-(thiophen-2-yl)pyridazine

Product 1

HCID 576545513-Benzyl-6-thiophen-2-yl-[1,2,4]triazolo[4,3-b]pyridazine

Procedure

The title compound was prepared as described in Example 17 from phenylacetic acid hydrazide (0.67 mmol) and 3-chloro-6-thiophen-2-yl-pyridazine (0.21 mmol). 1H NMR (400 MHz, CDCl3) δ 8.05 (1H, d, J=9.8 Hz), 7.66 (1H, dd, J=3.8 Hz, 1.3 Hz), 7.55 (1H, dd, J=5.0 Hz, 1.0 Hz), 7.53 (2H, m), 7.46 (1H, d, J=9.9 Hz), 7.31 (2H, m), 7.24 (1H, t, J=7.5 Hz), 7.17 (1H, dd, J=5.0 Hz, 3.8 Hz), 4.60 (2H, s). ESI-MS (m/z): Calcd for C16H12N4S: 292.1; found 293.2 (M+H).

Sources & evidence

ORD record
ord-08f316f59cf849569929768a0f6e6686
Source dataset
uspto-grants-2011_10
Patent number
US08030305B2

Reaction notes

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