3-Fluoro-4-(5-methylpyrrolo[2,1-f][1,2,4]triazin-4-yloxy)benzenamine → N-(3-Fluoro-4-(5-methylpyrrolo[2,1-f][1,2,4]triazin-4-yloxy)phenyl)-1-(4-fluorophenyl)-2-oxo-1,2-dihydropyridine-3-carboxamide

HRID 1393945Notes

Reaction equation

HRID 1393945 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH2:19])[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[C:14]2=[C:15]([CH3:18])[CH:16]=[CH:17][N:13]2[N:12]=[CH:11][N:10]=1.[F:20][C:21]1[CH:26]=[CH:25][C:24]([N:27]2[CH:32]=[CH:31][CH:30]=[C:29]([C:33](Cl)=[O:34])[C:28]2=[O:36])=[CH:23][CH:22]=1>ClCCl.N1C=CC=CC=1>[F:1][C:2]1[CH:3]=[C:4]([NH:19][C:33]([C:29]2[C:28](=[O:36])[N:27]([C:24]3[CH:23]=[CH:22][C:21]([F:20])=[CH:26][CH:25]=3)[CH:32]=[CH:31][CH:30]=2)=[O:34])[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[C:14]2=[C:15]([CH3:18])[CH:16]=[CH:17][N:13]2[N:12]=[CH:11][N:10]=1

Participants

5

Reactant 2

HCID 210816133-Fluoro-4-(5-methylpyrrolo[2,1-f][1,2,4]triazin-4-yloxy)benzenamineHCID 596809561-(4-Fluorophenyl)-2-oxo-1,2-dihydropyridine-3-carbonyl chloride

Product 1

HCID 16739700N-(3-Fluoro-4-(5-methylpyrrolo[2,1-f][1,2,4]triazin-4-yloxy)phenyl)-1-(4-fluorophenyl)-2-oxo-1,2-dihydropyridine-3-carboxamideYield 61.6%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 3-fluoro-4-(5-methylpyrrolo[2,1-f][1,2,4]triazin-4-yloxy)benzenamine (62 mg, 0.24 mmol) in dichloromethane (2 mL) and pyridine (0.5 mL), was added dropwise a solution of 1-(4-fluorophenyl)-2-oxo-1,2-dihydropyridine-3-carbonyl chloride (30 mg, 0.12 mmol) in dichloromethane (0.5 mL). The reaction mixture was stirred at rt for 30 min, and then concentrated to dryness. The residue was washed with methanol. The solid that formed was collected by filtration and dried under vaccum to give the title compound (35 mg, 61%). 1H NMR (DMSO-d6) δ 12.10 (br s, 1H), 8.58 (dd, 1H, J=7.15, 2.20 Hz), 8.12 (dd, 1H, J=6.60, 1.65 Hz), 7.98 (s, 1H), 7.95 (d, 2H, J=2.75 Hz), 7.62-7.58 (m, 2H), 7.40-7.47 (m, 4H), 6.78 (d, 1H, J=2.75 Hz), 6.72 (t, 1H, J=7.15 Hz), 2.54 (s, 3H); MS(ESI+) m/z 474.23 (M+H)+.

Workup

  1. concentrationconcentrated to dryness
  2. washThe residue was washed with methanol
  3. customThe solid that formed
  4. filtrationwas collected by filtration
  5. customdried under vaccum

Sources & evidence

ORD record
ord-b2ba73768861436891a148f409acedee
Source dataset
uspto-grants-2008_03
Patent number
US07348325B2

Reaction notes

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