Oxalyl chloride → 1-(4-Fluorophenyl)-2-oxo-1,2-dihydropyridine-3-carbonyl chloride

HRID 1393942Notes

Reaction equation

HRID 1393942 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14](O)=[O:15])[C:9]2=[O:17])=[CH:4][CH:3]=1.FC1C=C(NC(C2C(=O)N(C3C=CC(F)=CC=3)C=CC=2)=O)C=CC=1OC1C2=C(C)C(OCCN3CCN(C)CC3)=CN2N=CN=1.C(Cl)(=O)C([Cl:66])=O>CN(C=O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([Cl:66])=[O:15])[C:9]2=[O:17])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 65578Oxalyl chlorideHCID 16112844N-(3-Fluoro-4-(5-methyl-6-(2-(4-methylpiperazin-1-yl)ethoxy)pyrrolo[2,1-f][1,2,4]triazin-4-yloxy)phenyl)-1-(4-fluorophenyl)-2-oxo-1,2-dihydropyridine-3-carboxamideHCID 210815271-(4-Fluorophenyl)-2-oxo-1,2-dihydropyridine-3-carboxylic acid

Product 1

HCID 596809561-(4-Fluorophenyl)-2-oxo-1,2-dihydropyridine-3-carbonyl chlorideYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideCatalyst

Procedure

To a suspension of 1-(4-fluorophenyl)-2-oxo-1,2-dihydropyridine-3-carboxylic acid) (Compound J of Example 1) 475 mg, 2.04 mmol), was added oxalyl chloride (388 mg, 3 mmol), followed by one drop of DMF. The resulting mixture was stirred at rt for 1 h. The mixture was then concentrated in vacuo to afford the desired compound (500 mg, 100%) as a beige solid, which was used directly in the next step without further purification.

Workup

  1. concentrationThe mixture was then concentrated in vacuo

Sources & evidence

ORD record
ord-6c70b606fc9f4afe95dd260297576a66
Source dataset
uspto-grants-2008_03
Patent number
US07348325B2

Reaction notes

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