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

HRID 1661797Notes

Reaction equation

HRID 1661797 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([NH:11][NH2:12])=O)=[CH:4][CH:3]=1.Cl[C:14]1[N:15]=[N:16][C:17]([C:20]2[S:21][CH:22]=[CH:23][CH:24]=2)=[CH:18][CH:19]=1>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]2[N:15]3[N:16]=[C:17]([C:20]4[S:21][CH:22]=[CH:23][CH:24]=4)[CH:18]=[CH:19][C:14]3=[N:12][N:11]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 37716122-(4-Fluorophenyl)acetohydrazideHCID 64047013-Chloro-6-(thiophen-2-yl)pyridazine

Product 1

HCID 576545823-(4-Fluoro-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-fluorophenylacetic acid hydrazide (1.04 mmol) and 3-chloro-6-thiophen-2-yl-pyridazine (0.52 mmol) as a pale beige solid. 1H NMR (CD3OD) δ 8.19 (1H, d, J=9.9 Hz), 7.93 (1H, dd, J=3.8 Hz, 0.9 Hz), 7.90 (1H, d, J =9.9 Hz), 7.75 (1H, dd, J=5.0 Hz, 1.0 Hz), 7.50 (2H, dd, J=9.0 Hz, 5.3 Hz), 7.24 (1H, dd, J=5.3 Hz, 3.8 Hz), 7.06 (2H, t, J=8.8 Hz), 4.59 (2H, s). ESI-MS (m/z): Calcd for C16H11FN4S: 310.1; found 311.2 (M+H).

Sources & evidence

ORD record
ord-da97e830c35d46059841c0085dc5ad00
Source dataset
uspto-grants-2011_10
Patent number
US08030305B2

Reaction notes

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