Aniline → 2-(imidazo[1,2-b]pyridazin-6-ylthio)-N-phenylbenzamide

HRID 1664065Notes

Reaction equation

HRID 1664065 reaction equation
[N:1]1[CH:2]=[CH:3][N:4]2[C:9]=1[CH:8]=[CH:7][C:6]([S:10][C:11]1[CH:19]=[CH:18][CH:17]=[CH:16][C:12]=1[C:13]([OH:15])=O)=[N:5]2.[NH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.C(N(CC)CC)C.[OH-].[Na+]>CN(C)C=O>[N:1]1[CH:2]=[CH:3][N:4]2[C:9]=1[CH:8]=[CH:7][C:6]([S:10][C:11]1[CH:19]=[CH:18][CH:17]=[CH:16][C:12]=1[C:13]([NH:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:15])=[N:5]2

Participants

8

Reactant 6

HCID 6115AnilineHCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 574410642-(Imidazo[1,2-b]pyridazin-6-ylthio)benzoic acid

Product 1

HCID 575057832-(imidazo[1,2-b]pyridazin-6-ylthio)-N-phenylbenzamideYield 80%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 2-(imidazo[1,2-b]pyridazin-6-ylthio)benzoic acid (109 mg, 0.40 mmol), aniline (75 mg, 0.81 mmol), 1-hydroxybenzotriazole hydrate (61 mg, 0.40 mmol) and N,N-dimethylformamide (5 mL) were added 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (153 mg, 0.80 mmol) and triethylamine (0.167 mL, 1.20 mmol), and the mixture was stirred at room temperature for 18 hr. A 1N aqueous sodium hydroxide solution was added to the mixture and the mixture was extracted with ethyl acetate. The organic layer was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/methanol=100/0→80/20) and precipitated from ethyl acetate/diisopropyl ether to give the title compound (110 mg, 0.32 mmol, yield 79%) as a white solid.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. concentrationThe organic layer was concentrated under reduced pressure
  3. customthe residue was purified by silica gel column chromatography (ethyl acetate/methanol=100/0→80/20)
  4. customprecipitated from ethyl acetate/diisopropyl ether

Sources & evidence

ORD record
ord-640005b434a54b5ab250e96373413975
Source dataset
uspto-grants-2011_10
Patent number
US08034812B2

Reaction notes

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