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

HRID 456099

반응식

HRID 456099 반응식
[F:1][C:2]([F:25])([C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][CH:24]=1)[N:21]=[CH:20][CH:19]=[CH:18]2)[C:3]1[N:7]2[N:8]=[C:9]([C:12](=O)[CH3:13])[CH:10]=[CH:11][C:6]2=[N:5][N:4]=1.[NH2:26][N:27]1[CH2:31][C:30](=[O:32])[NH:29][C:28]1=[O:33]>CO>[F:1][C:2]([F:25])([C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][CH:24]=1)[N:21]=[CH:20][CH:19]=[CH:18]2)[C:3]1[N:7]2[N:8]=[C:9](/[C:12](=[N:26]/[N:27]3[CH2:31][C:30](=[O:32])[NH:29][C:28]3=[O:33])/[CH3:13])[CH:10]=[CH:11][C:6]2=[N:5][N:4]=1

참가 물질

4

반응물 2

HCID 728231-AminohydantoinHCID 581904681-(3-(Difluoro(quinolin-6-yl)methyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)ethanone

생성물 1

HCID 716998961-[(E)-1-[3-[difluoro(quinolin-6-yl)methyl]-[1,2,4]triazolo[4,3-b]pyridazin-6-yl]ethylideneamino]imidazolidine-2,4-dione수율 23.7%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

A solution of 1-(3-(difluoro(quinolin-6-yl)methyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)ethanone (20 mg, 0.059 mmol) and 1-aminoimidazolidine-2,4-dione (13.6 mg, 0.12 mmol) was stirred in MeOH at room temperature over a weekend. Light yellow solid was filtered to give the title compound (6 mg, 0.014 mmol). The filtrate was purified on HPLC (acidic with 0.05% TFA) to give the title compound as TFA salt (8 mg, 0.0145 mmol). The combined yield was 48%. 1H-NMR (400 MHz, DMSO-d6) δ ppm 11.46 (s, 1H), 9.02 (d, 1H), 8.55 (d, 1H), 8.48 (s, 1H), 8.46 (s, 1H), 8.18 (d, 1H), 8.0 (s, 1H), 7.98 (s, 1H), 7.65 (d, 1H), 4.54 (s, 2H), 2.24 (s, 3H). LCMS (method B): [MH]+=437.1, tR=2.06 min.

후처리

  1. filtrationLight yellow solid was filtered

출처 및 근거

ORD 기록
ord-8d7755e77f56488fbbc965803727bbac
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08497368B2

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