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

HRID 456071Notes

Reaction equation

HRID 456071 reaction equation
[CH3:1][N:2]([C:4]([NH2:6])=[O:5])[NH2:3].[F:7][C:8]1[CH:17]=[C:16]2[C:11]([CH:12]=[CH:13][CH:14]=[N:15]2)=[CH:10][C:9]=1[CH2:18][C:19]1[N:23]2[N:24]=[C:25]([C:28](=O)[CH3:29])[CH:26]=[CH:27][C:22]2=[N:21][CH:20]=1>>[F:7][C:8]1[CH:17]=[C:16]2[C:11]([CH:12]=[CH:13][CH:14]=[N:15]2)=[CH:10][C:9]=1[CH2:18][C:19]1[N:23]2[N:24]=[C:25](/[C:28](=[N:3]/[N:2]([CH3:1])[C:4]([NH2:6])=[O:5])/[CH3:29])[CH:26]=[CH:27][C:22]2=[N:21][CH:20]=1

Participants

3

Reactant 2

HCID 2560041-Amino-1-methylureaHCID 581905991-[3-(7-Fluoro-quinolin-6-ylmethyl)-imidazo[1,2-b]pyridazin-6-yl]ethanone

Product 1

HCID 716998721-[(E)-1-[3-[(7-fluoroquinolin-6-yl)methyl]imidazo[1,2-b]pyridazin-6-yl]ethylideneamino]-1-methylureaYield 21%

Procedure

The title compound was prepared from 1-methylhydrazine 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), 8.05 (s, 2H), 7.97 (d, 1H), 7.77 (d, 1H), 7.72 (s, 1H), 7.47 (q, 1H), 6.54 (s, 2H), 4.58 (s, 2H), 3.19 (s, 3H), 2.37 (s, 3H). LCMS (method A): [MH]+=392, tR=4.76 min.

Sources & evidence

ORD record
ord-761cac01526c49a4b34243ff596fdf04
Source dataset
uspto-grants-2013_07
Patent number
US08497368B2

Reaction notes

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