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

HRID 456064Notes

Reaction equation

HRID 456064 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[CH2:12][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.[NH2:26][NH:27][C:28]([NH2:30])=[O:29].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[CH2:12][C:13]1[N:17]2[N:18]=[C:19](/[C:22](=[N:26]/[NH:27][C:28]([NH2:30])=[O:29])/[CH3:23])[CH:20]=[CH:21][C:16]2=[N:15][CH:14]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 11236Semicarbazide hydrochlorideHCID 581905991-[3-(7-Fluoro-quinolin-6-ylmethyl)-imidazo[1,2-b]pyridazin-6-yl]ethanone

Product 1

HCID 50915827[(E)-1-[3-[(7-fluoroquinolin-6-yl)methyl]imidazo[1,2-b]pyridazin-6-yl]ethylideneamino]ureaYield 66.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1-[3-(7-fluoro-quinolin-6-ylmethyl)-imidazo[1,2-b]pyridazin-6-yl]-ethanone (320 mg, 1 mmol) in methanol (30 mL) was added semicarbazide hydrochloride (334 mg, 3.0 mmol). Triethyl amine was added dropwise to the reaction mixture 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 250 mg (yield: 66%) title compound as a white solid. 1H-NMR 400 MHz, DMSO-d6) δ ppm 9.69 (s, 1H), 8.85 (dd, 1H), 8.30 (d, 1H), 8.21 (d, 1H), 7.98 (d, 1H), 7.94 (d, 1H), 7.77 (d, 1H), 7.66 (s, 1H), 7.47 (q, 1H), 6.73 (b, 2H), 4.56 (s, 2H), 2.23 (s, 3H). LCMS (method A): [MH]+=378, tR=4.64 min.

Workup

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

Sources & evidence

ORD record
ord-17d5bcf3ec274a46a2404b7f809c5d0c
Source dataset
uspto-grants-2013_07
Patent number
US08497368B2

Reaction notes

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