Triethylamine → Methyl 6-[[bis(5-fluoro-2-methylbenzoyl)]amino]pyridine-3-carboxylate

HRID 1735217Notes

Reaction equation

HRID 1735217 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]([O:10][CH3:11])=[O:9])=[CH:4][CH:3]=1.C(N([CH2:17][CH3:18])CC)C.[F:19][C:20]1[CH:21]=[CH:22][C:23]([CH3:29])=[C:24]([CH:28]=1)[C:25](Cl)=[O:26]>ClCCl>[F:19][C:20]1[CH:21]=[CH:22][C:17]([CH3:18])=[C:24]([CH:28]=1)[C:25]([N:1]([C:25](=[O:26])[C:24]1[CH:28]=[C:20]([F:19])[CH:21]=[CH:22][C:23]=1[CH3:29])[C:2]1[N:7]=[CH:6][C:5]([C:8]([O:10][CH3:11])=[O:9])=[CH:4][CH:3]=1)=[O:26]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 737487Methyl 6-aminonicotinateHCID 27373835-Fluoro-2-methylbenzoyl chloride2×

Product 1

HCID 22099733Methyl 6-[[bis(5-fluoro-2-methylbenzoyl)]amino]pyridine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of 4.5 g of methyl 6-aminopyridine-3-carboxylate and 5.53 ml of triethylamine in 40 ml of dichloromethane (cooled in an ice bath) is added 6.38 g of 5-fluoro-2-methylbenzoyl chloride in 10 ml of dichloromethane. The mixture is stirred at room temperature under argon for 18 hours and an additional 3.4 g of 5-fluoro-2-methylbenzoyl chloride added. After stirring at room temperature for 3 hours, the mixture is filtered to give 3.0 g of methyl 6-[[bis(5-fluoro-2-methylbenzoyl)]amino]pyridine-3-carboxylate. The filtrate is concentrated to dryness and the residue triturated with hexane and ethyl acetate to give an additional 9.0 g of bis acylated compound.

Workup

  1. stirringAfter stirring at room temperature for 3 hours
  2. filtrationthe mixture is filtered

Sources & evidence

ORD record
ord-b14a9db0a08949049a3938381863939e
Source dataset
uspto-grants-1996_07
Patent number
US05536718

Reaction notes

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