1-Aminohydantoin → 1-[(E)-1-[3-(quinolin-6-ylmethyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl]ethylideneamino]imidazolidine-2,4-dione

HRID 456104

Reaction equation

HRID 456104 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][C:7]([CH2:11][C:12]3[N:16]4[N:17]=[C:18]([C:21](=O)[CH3:22])[CH:19]=[CH:20][C:15]4=[N:14][N:13]=3)=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[NH2:24][N:25]1[CH2:29][C:28](=[O:30])[NH:27][C:26]1=[O:31]>>[N:1]1[C:10]2[C:5](=[CH:6][C:7]([CH2:11][C:12]3[N:16]4[N:17]=[C:18](/[C:21](=[N:24]/[N:25]5[CH2:29][C:28](=[O:30])[NH:27][C:26]5=[O:31])/[CH3:22])[CH:19]=[CH:20][C:15]4=[N:14][N:13]=3)=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 2

HCID 728231-AminohydantoinHCID 581904611-(3-(Quinolin-6-ylmethyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)ethanone

Product 1

HCID 716999001-[(E)-1-[3-(quinolin-6-ylmethyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl]ethylideneamino]imidazolidine-2,4-dioneYield 51%

Procedure

The title compound (20 mg, 51%) was synthesized from 1-(3-(quinolin-6-ylmethyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)ethanone (30 mg, 0.1 mmol) and 1-aminoimidazolidine-2,4-dione (22.77 mg, 0.198 mmol) using the same procedure as described in the synthesis of example 37. 1H-NMR (400 MHz, DMSO-d6) δ ppm 11.44 (s, 1H), 9.05 (d, 1H), 8.70 (d, 1H), 8.32 (d, 1H), 8.12 (d, 2H), 7.98 (d, 1H), 7.87 (d, 1H), 7.77 (m, 1H), 4.83 (s, 2H), 4.54 (s, 2H), 2.40 (s, 3H). LCMS (method B): [MH]+=401.1, tR=1.64 min.

Workup

  1. customas described in the synthesis of example 37

Sources & evidence

ORD record
ord-fbcd8ee8419c4c70a6e613b96f9e5e2d
Source dataset
uspto-grants-2013_07
Patent number
US08497368B2

Linked notes

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