2-(4-Methoxyphenyl)acetohydrazide → 3-(4-Methoxy-benzyl)-6-thiophen-2-yl-[1,2,4]triazolo[4,3-b]pyridazine

HRID 1661796Notes

Reaction equation

HRID 1661796 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([NH:12][NH2:13])=O)=[CH:5][CH:4]=1.Cl[C:15]1[N:16]=[N:17][C:18]([C:21]2[S:22][CH:23]=[CH:24][CH:25]=2)=[CH:19][CH:20]=1>>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]2[N:16]3[N:17]=[C:18]([C:21]4[S:22][CH:23]=[CH:24][CH:25]=4)[CH:19]=[CH:20][C:15]3=[N:13][N:12]=2)=[CH:5][CH:4]=1

Participants

3

Reactant 2

HCID 5784632-(4-Methoxyphenyl)acetohydrazideHCID 64047013-Chloro-6-(thiophen-2-yl)pyridazine

Product 1

HCID 576545553-(4-Methoxy-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 4-methoxy-phenylacetic acid hydrazide (1.39 mmol) and 3-chloro-6-thiophen-2-yl-pyridazine (0.32 mmol) as a pale orange solid. 1H NMR (CD3OD) δ 8.17 (1H, d, J=9.8 Hz), 7.92 (1H, dd, J=3.8 Hz, 1.2 Hz), 7.88 (1H, d, J =9.9 Hz), 7.74 (1H, dd, J=5.0 Hz, 1.0 Hz), 7.40 (2H, d, J=8.8 Hz), 7.23 (1H, dd, J =5.0 Hz, 3.8 Hz), 6.88 (2H, d, J=8.9 Hz,), 4.51 (s, 2H), 3.75 (3H, s). ESI-MS (m/z): Calcd for C17H14N4OS: 322.1; found 323.2 (M+H).

Sources & evidence

ORD record
ord-c912c0f883014460b1068974744db881
Source dataset
uspto-grants-2011_10
Patent number
US08030305B2

Reaction notes

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