Semicarbazide hydrochloride → [(E)-1-[3-[(4,6-difluoro-1-methylindazol-5-yl)methyl]imidazo[1,2-b]pyridazin-6-yl]ethylideneamino]urea

HRID 456096Notes

Reaction equation

HRID 456096 reaction equation
[F:1][C:2]1[C:10]([CH2:11][C:12]2[N:16]3[N:17]=[C:18]([C:21](=O)[CH3:22])[CH:19]=[CH:20][C:15]3=[N:14][CH:13]=2)=[C:9]([F:24])[CH:8]=[C:7]2[C:3]=1[CH:4]=[N:5][N:6]2[CH3:25].Cl.[NH:27]([C:29]([NH2:31])=[O:30])[NH2:28]>CO>[F:1][C:2]1[C:10]([CH2:11][C:12]2[N:16]3[N:17]=[C:18](/[C:21](=[N:28]/[NH:27][C:29]([NH2:31])=[O:30])/[CH3:22])[CH:19]=[CH:20][C:15]3=[N:14][CH:13]=2)=[C:9]([F:24])[CH:8]=[C:7]2[C:3]=1[CH:4]=[N:5][N:6]2[CH3:25]

Participants

4

Reactant 2

HCID 11236Semicarbazide hydrochlorideHCID 581904931-(3-((4,6-Difluoro-1-methyl-1H-indazol-5-yl)methyl)imidazo[1,2-b]pyridazin-6-yl)ethanone

Product 1

HCID 71699894[(E)-1-[3-[(4,6-difluoro-1-methylindazol-5-yl)methyl]imidazo[1,2-b]pyridazin-6-yl]ethylideneamino]ureaYield 62.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 1-(3-((4,6-difluoro-1-methyl-1H-indazol-5-yl)methyl)imidazo[1,2-b]pyridazin-6-yl)ethanone (45 mg, 0.099 mmol, 75% pure) and hydrazinecarboxamide hydrochloride (22 mg, 0.198 mmol) in 10 mL MeOH was stirred at room temperature overnight. Solvent was evaporated and the residue was dissolved in a small amount of MeOH. Precipitates formed and was filtered to give the title compound as a white solid (25 mg, 0.062 mmol). 1H-NMR (400 MHz, DMSO-d6) δ ppm 9.95 (s, 1H), 8.62 (d, 1H), 8.20 (s, 1H), 8.17 (s, 1H), 8.0 (s, 1H), 7.54 (d, 1H), 6.85 (broad, 2H), 4.48 (s, 2H), 4.0 (s, 3H), 2.3 (s, 3H). LCMS (method B): [MH]+=398.9, tR=2.17 min.

Workup

  1. customSolvent was evaporated
  2. dissolutionthe residue was dissolved in a small amount of MeOH
  3. customPrecipitates
  4. customformed
  5. filtrationwas filtered

Sources & evidence

ORD record
ord-cf37acb6a29f46d294fe5ecbacb8a732
Source dataset
uspto-grants-2013_07
Patent number
US08497368B2

Reaction notes

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