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

HRID 456163Notes

Reaction equation

HRID 456163 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([CH:11]([C:13]3[N:17]4[N:18]=[C:19]([C:22](=O)[CH3:23])[CH:20]=[CH:21][C:16]4=[N:15][CH:14]=3)[CH3:12])=[CH:8][CH:9]=2)[CH:4]=[N:3]1.[NH:25]([C:27]([NH2:29])=[O:28])[NH2:26]>>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([CH:11]([C:13]3[N:17]4[N:18]=[C:19](/[C:22](=[N:26]/[NH:25][C:27]([NH2:29])=[O:28])/[CH3:23])[CH:20]=[CH:21][C:16]4=[N:15][CH:14]=3)[CH3:12])=[CH:8][CH:9]=2)[CH:4]=[N:3]1

Participants

3

Reactant 2

HCID 5196SemicarbazideHCID 581904911-(3-(1-(1-Methyl-1H-indazol-5-yl)ethyl)imidazo[1,2-b]pyridazin-6-yl)ethanone

Product 1

HCID 71699926[(E)-1-[3-[1-(1-methylindazol-5-yl)ethyl]imidazo[1,2-b]pyridazin-6-yl]ethylideneamino]ureaYield 62%

Procedure

The title compound (14.0 mg, 59%) was synthesized from 1-(3-(1-(1-methyl-1H-indazol-5-yl)ethyl)imidazo[1,2-b]pyridazin-6-yl)ethanone (20.0 mg, 0.06 mmol) and hydrazinecarboxamide (13.97 mg, 0.13 mmol) using the same procedure as described in the synthesis of example 69. 1H-NMR (400 MHz, CDCl3) δ ppm 8.33 (s, 1H), 7.87 (m, 2H), 7.66 (m, 3H), 7.32 (m, 2H), 4.74 (q, 1H), 4.03 (s, 3H), 2.24 (s, 3H), 1.84 (d, 3H). LCMS (method A): [MH]+=377, tR=4.70 min.

Workup

  1. customas described in the synthesis of example 69

Sources & evidence

ORD record
ord-0a8506fa90ca47ca88a8b719432c94e0
Source dataset
uspto-grants-2013_07
Patent number
US08497368B2

Reaction notes

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