4-Phenylsemicarbazide → 1-[(E)-1-[3-[(7-fluoroquinolin-6-yl)methyl]imidazo[1,2-b]pyridazin-6-yl]ethylideneamino]-3-phenylurea

HRID 456069

Reaction equation

HRID 456069 reaction equation
[C:1]1([NH:7][C:8]([NH:10][NH2:11])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F:12][C:13]1[CH:22]=[C:21]2[C:16]([CH:17]=[CH:18][CH:19]=[N:20]2)=[CH:15][C:14]=1[CH2:23][C:24]1[N:28]2[N:29]=[C:30]([C:33](=O)[CH3:34])[CH:31]=[CH:32][C:27]2=[N:26][CH:25]=1>>[F:12][C:13]1[CH:22]=[C:21]2[C:16]([CH:17]=[CH:18][CH:19]=[N:20]2)=[CH:15][C:14]=1[CH2:23][C:24]1[N:28]2[N:29]=[C:30](/[C:33](=[N:11]/[NH:10][C:8]([NH:7][C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[O:9])/[CH3:34])[CH:31]=[CH:32][C:27]2=[N:26][CH:25]=1

Participants

3

Reactant 2

HCID 108374-PhenylsemicarbazideHCID 581905991-[3-(7-Fluoro-quinolin-6-ylmethyl)-imidazo[1,2-b]pyridazin-6-yl]ethanone

Product 1

HCID 716998701-[(E)-1-[3-[(7-fluoroquinolin-6-yl)methyl]imidazo[1,2-b]pyridazin-6-yl]ethylideneamino]-3-phenylureaYield 36%

Procedure

The title compound was prepared from N-phenylhydrazine carboxamide and 1-[3-(7-fluoro-quinolin-6-ylmethyl)-imidazo[1,2-b]pyridazin-6-yl]-ethanone in analogy to the synthesis of example 1 in 36% yield. 1H-NMR (400 MHz, DMSO-d6) δ ppm 10.13 (s, 1H), 9.06 (s, 1H), 8.86 (dd, 1H), 8.30 (t, 2H), 8.06 (d, 1H), 7.96 (d, 1H), 7.78 (d, 1H), 7.69 (s, 1H), 7.60 (d, 2H), 7.48 (q, 1H), 7.31 (t, 2H), 7.04 (t, 1H), 4.58 (s, 2H), 2.32 (s, 3H). LCMS (method C): [MH]+=454, tR=3.89 min.

Sources & evidence

ORD record
ord-ddb170f9f13a439f903c2b3744074ac6
Source dataset
uspto-grants-2013_07
Patent number
US08497368B2

Linked notes

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