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Semicarbazide → [(E)-1-[3-[(1-methylindazol-5-yl)methyl]imidazo[1,2-b]pyridazin-6-yl]ethylideneamino]urea

HRID 456157
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HRID 456157 반응식
[CH3:1][N:2]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][CH:13]=3)=[CH:8][CH:9]=2)[CH:4]=[N:3]1.[NH:24]([C:26]([NH2:28])=[O:27])[NH2:25]>C1COCC1>[CH3:1][N:2]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:25]/[NH:24][C:26]([NH2:28])=[O:27])/[CH3:22])[CH:19]=[CH:20][C:15]4=[N:14][CH:13]=3)=[CH:8][CH:9]=2)[CH:4]=[N:3]1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

4

반응물 2

HCID 5196SemicarbazideHCID 581905161-(3-((1-Methyl-1H-indazol-5-yl)methyl)imidazo[1,2-b]pyridazin-6-yl)ethanone

생성물 1

HCID 71699925[(E)-1-[3-[(1-methylindazol-5-yl)methyl]imidazo[1,2-b]pyridazin-6-yl]ethylideneamino]urea수율 88.9%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A solution of 1-(3-((1-methyl-1H-indazol-5-yl)methyl)imidazo[1,2-b]pyridazin-6-yl)ethanone (40.0 mg, 0.09 mmol) and hydrazinecarboxamide (19.47 mg, 0.26 mmol) in 10 mL THF was stirred at 40° C. for overnight. Solvent was removed in vacuo. The crude product was purified on flash chromatography (DCM:MeOH=20:1) to give the title compound as a white solid (29.0 mg, 88%). 1H-NMR (400 MHz, DMSO-d6) δ ppm 9.71 (s, 1H), 8.18 (d, 1H), 7.95 (m, 2H), 7.69 (s, 1H), 7.60 (s, 1H), 7.75 (d, 1H), 7.40 (dd, 1H), 6.76 (bs, 2H), 4.41 (s, 2H), 3.99 (s, 3H), 2.29 (s, 3H). LCMS (method A): [MH]+=363, tR=4.42 min.

후처리

  1. customSolvent was removed in vacuo
  2. customThe crude product was purified on flash chromatography (DCM:MeOH=20:1)

출처 및 근거

ORD 기록
ord-e90edb6ad4e24c46ae64d35617b67ebe
출처 데이터셋
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08497368B2

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