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

HRID 456073

Reaction equation

HRID 456073 reaction equation
[NH2:1][N:2]1[CH2:6][CH2:5][O:4][C:3]1=[O:7].[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:1]/[N:2]3[CH2:6][CH2:5][O:4][C:3]3=[O:7])/[CH3:30])[CH:27]=[CH:28][C:23]2=[N:22][CH:21]=1

Participants

3

Reactant 2

HCID 657253-Amino-2-oxazolidinoneHCID 581905991-[3-(7-Fluoro-quinolin-6-ylmethyl)-imidazo[1,2-b]pyridazin-6-yl]ethanone

Product 1

HCID 716998743-[(E)-1-[3-[(7-fluoroquinolin-6-yl)methyl]imidazo[1,2-b]pyridazin-6-yl]ethylideneamino]-1,3-oxazolidin-2-oneYield 24%

Procedure

The title compound was prepared from 3-aminooxazolidin-2-one 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 24% yield. 1H-NMR (400 MHz, CDCl3) δ ppm 8.85 (dd, 1H), 8.02 (d, 1H), 7.88 (m, 2H), 7.71 (m, 3H), 7.33 (q, 1H), 4.58 (s, 2H), 4.51 (t, 2H), 4.01 (t, 2H), 2.49 (s, 3H). LCMS (method A): [MH]+=405, tR=4.76 min.

Sources & evidence

ORD record
ord-3b5abdacef854cb99d413e07199c062d
Source dataset
uspto-grants-2013_07
Patent number
US08497368B2

Linked notes

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