Triethylamine → [(E)-1-[3-[(7-fluoroquinolin-6-yl)-hydroxymethyl]imidazo[1,2-b]pyridazin-6-yl]ethylideneamino]urea

HRID 456082Notes

Reaction equation

HRID 456082 reaction equation
[F:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[N:9]2)=[CH:4][C:3]=1[CH:12]([OH:25])[C:13]1[N:17]2[N:18]=[C:19]([C:22](=O)[CH3:23])[CH:20]=[CH:21][C:16]2=[N:15][CH:14]=1.Cl.[NH2:27][NH:28][C:29]([NH2:31])=[O:30].C(N(CC)CC)C>CO>[F:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[N:9]2)=[CH:4][C:3]=1[CH:12]([OH:25])[C:13]1[N:17]2[N:18]=[C:19](/[C:22](=[N:27]/[NH:28][C:29]([NH2:31])=[O:30])/[CH3:23])[CH:20]=[CH:21][C:16]2=[N:15][CH:14]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 11236Semicarbazide hydrochlorideHCID 66927089HCID 66927089, compound

Product 1

HCID 71699884[(E)-1-[3-[(7-fluoroquinolin-6-yl)-hydroxymethyl]imidazo[1,2-b]pyridazin-6-yl]ethylideneamino]ureaYield 47.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1-(3-((7-fluoroquinolin-6-yl)(hydroxy)methyl)imidazo[1,2-b]pyridazin-6-yl)ethanone (100 mg, 0.27 mmol) in methanol (15 mL) was added semicarbazide hydrochloride (45 mg, 0.41 mmol). Triethyl amine was added dropwise to adjust the pH to 5-6. The reaction mixture was stirred at room temperature overnight. The precipitate was collected by filtration and dried over vacuum pump to afford 50 mg (yield: 47%) title compound as a white solid. 1H-NMR (400 MHz, DMSO-d6) δ ppm 9.68 (s, 1H), 8.89 (dd, 1H), 8.45 (d, 1H), 8.25 (m, 2H), 7.99 (d, 1H), 7.72 (d, 1H), 7.57 (s, 1H), 7.52 (q, 1H), 6.67 (b, 2H), 6.62 (s, 1H), 6.47 (b, 1H), 2.19 (s, 3H). LCMS (method A): [MH]+=394, tR=3.95 min.

Workup

  1. filtrationThe precipitate was collected by filtration
  2. customdried over vacuum pump

Sources & evidence

ORD record
ord-bf399b70f4034a34ad6300e98ad17bc8
Source dataset
uspto-grants-2013_07
Patent number
US08497368B2

Reaction notes

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