N,1-Dimethylhydrazine-1-carboxamide → 1-[(E)-1-[3-[(7-fluoroquinolin-6-yl)methyl]imidazo[1,2-b]pyridazin-6-yl]ethylideneamino]-1,3-dimethylurea

HRID 456072

Reaction equation

HRID 456072 reaction equation
[CH3:1][NH:2][C:3]([N:5]([CH3:7])[NH2:6])=[O:4].[F:8][C:9]1[CH:18]=[C:17]2[C:12]([CH:13]=[CH:14][CH:15]=[N:16]2)=[CH:11][C:10]=1[CH2:19][C:20]1[N:24]2[N:25]=[C:26]([C:29](=O)[CH3:30])[CH:27]=[CH:28][C:23]2=[N:22][CH:21]=1>>[F:8][C:9]1[CH:18]=[C:17]2[C:12]([CH:13]=[CH:14][CH:15]=[N:16]2)=[CH:11][C:10]=1[CH2:19][C:20]1[N:24]2[N:25]=[C:26](/[C:29](=[N:6]/[N:5]([CH3:7])[C:3]([NH:2][CH3:1])=[O:4])/[CH3:30])[CH:27]=[CH:28][C:23]2=[N:22][CH:21]=1

Participants

3

Reactant 2

HCID 304021N,1-Dimethylhydrazine-1-carboxamideHCID 581905991-[3-(7-Fluoro-quinolin-6-ylmethyl)-imidazo[1,2-b]pyridazin-6-yl]ethanone

Product 1

HCID 716998731-[(E)-1-[3-[(7-fluoroquinolin-6-yl)methyl]imidazo[1,2-b]pyridazin-6-yl]ethylideneamino]-1,3-dimethylureaYield 21%

Procedure

The title compound was prepared from N,1-dimethylhydrazine 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 21% yield. 1H-NMR (400 MHz, DMSO-d6) δ ppm 8.86 (dd, 1H), 8.31 (d, 1H), 8.06 (m, 2H), 7.97 (d, 1H), 7.77 (d, 1H), 7.73 (s, 1H), 7.47 (q, 1H), 6.90 (q, 1H), 4.59 (s, 2H), 3.19 (s, 3H), 2.68 (d, 3H), 2.37 (s, 3H). LCMS (method B): [MH]+=406, tR=2.27 min.

Sources & evidence

ORD record
ord-209bec646ed747fba0c39c0788c11f52
Source dataset
uspto-grants-2013_07
Patent number
US08497368B2

Linked notes

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