2-Hydrazinobenzoxazole → N-[(E)-1-[3-[(7-fluoroquinolin-6-yl)methyl]imidazo[1,2-b]pyridazin-6-yl]ethylideneamino]-1,3-benzoxazol-2-amine

HRID 456075Notes

Reaction equation

HRID 456075 reaction equation
[NH:1]([C:3]1[O:4][C:5]2[CH:11]=[CH:10][CH:9]=[CH:8][C:6]=2[N:7]=1)[NH2:2].[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:2]/[NH:1][C:3]3[O:4][C:5]4[CH:11]=[CH:10][CH:9]=[CH:8][C:6]=4[N:7]=3)/[CH3:34])[CH:31]=[CH:32][C:27]2=[N:26][CH:25]=1

Participants

3

Reactant 2

HCID 3038622-HydrazinobenzoxazoleHCID 581905991-[3-(7-Fluoro-quinolin-6-ylmethyl)-imidazo[1,2-b]pyridazin-6-yl]ethanone

Product 1

HCID 71699876N-[(E)-1-[3-[(7-fluoroquinolin-6-yl)methyl]imidazo[1,2-b]pyridazin-6-yl]ethylideneamino]-1,3-benzoxazol-2-amineYield 74%

Procedure

The title compound was prepared from 2-hydrazinylbenzo[d]oxazole 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 74% yield. 1H-NMR (400 MHz, DMSO-d6) δ ppm 11.8-11.5 (m, 1H), 8.87 (dd, 1H), 8.4-7.9 (m, 4), 7.8-7.6 (m, 2H), 7.6-7.1 (m, 5H), 4.58 (s, 2H), 2.49 (s, 3H). LCMS (method C): [MH]+=452, tR=4.42 min.

Sources & evidence

ORD record
ord-dc3c32edaa064170b8e00efb62867f63
Source dataset
uspto-grants-2013_07
Patent number
US08497368B2

Reaction notes

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