Triethylamine → N-[5-(2,6-difluorophenyl)-6-oxo-6H-pyrido[1,2-b]pyridazin-2-yl]-N'-(2-fluorophenyl)urea

HRID 1454972Notes

Reaction equation

HRID 1454972 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[CH:9][C:10](=[O:20])[C:11]=2[C:12]2[C:17]([F:18])=[CH:16][CH:15]=[CH:14][C:13]=2[F:19])[N:7]=1.C(N(CC)CC)C.[F:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[N:35]=[C:36]=[O:37]>C1(C)C=CC=CC=1>[F:18][C:17]1[CH:16]=[CH:15][CH:14]=[C:13]([F:19])[C:12]=1[C:11]1[C:10](=[O:20])[CH:9]=[CH:8][N:6]2[C:5]=1[CH:4]=[CH:3][C:2]([NH:1][C:36]([NH:35][C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=1[F:28])=[O:37])=[N:7]2

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 855882-Fluorophenyl isocyanateHCID 575312362-amino-5-(2,6-difluorophenyl)-6H-pyrido[1,2-b]pyridazin-6-one

Product 1

HCID 16749959N-[5-(2,6-difluorophenyl)-6-oxo-6H-pyrido[1,2-b]pyridazin-2-yl]-N'-(2-fluorophenyl)urea

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2-amino-5-(2,6-difluorophenyl)-6H-pyrido[1,2-b]pyridazin-6-one (50 mg, 0.18 mmol), toluene (3 mL), triethyl amine (36 mg, 0.36 mmol), and 1-fluoro-2-isocyanatobenzene (49 mg, 0.36 mmol) were added to a flask and heated to reflux. The reaction was complete in 3 hrs and concentrated to dryness. The crude residue was purified via silica gel chromatography (CH2Cl2/EtOAc/MeOH) to yield the title compound.

Workup

  1. temperatureheated to reflux
  2. concentrationconcentrated to dryness
  3. customThe crude residue was purified via silica gel chromatography (CH2Cl2/EtOAc/MeOH)

Sources & evidence

ORD record
ord-6d0e8eb151bd4bf3af638deb78180d00
Source dataset
uspto-grants-2009_01
Patent number
US07482345B2

Reaction notes

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