Ammonia → 4-(4-Bromo-2-fluoroanilino)-1-methyl-6-oxo-1,6-dihydro-3-pyridinecarboxamide

HRID 917754Notes

Reaction equation

HRID 917754 reaction equation
[Br:1][C:2]1[CH:30]=[CH:29][C:5]([NH:6][C:7]2[C:8]([C:15](OC3C(F)=C(F)C(F)=C(F)C=3F)=[O:16])=[CH:9][N:10]([CH3:14])[C:11](=[O:13])[CH:12]=2)=[C:4]([F:31])[CH:3]=1.[NH3:32]>C1COCC1>[Br:1][C:2]1[CH:30]=[CH:29][C:5]([NH:6][C:7]2[C:8]([C:15]([NH2:32])=[O:16])=[CH:9][N:10]([CH3:14])[C:11](=[O:13])[CH:12]=2)=[C:4]([F:31])[CH:3]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 589628492,3,4,5,6-Pentafluorophenyl 4-(4-bromo-2-fluoroanilino)-1-methyl-6-oxo-1,6-dihydro-3-pyridinecarboxylate

Product 1

HCID 114392194-(4-Bromo-2-fluoroanilino)-1-methyl-6-oxo-1,6-dihydro-3-pyridinecarboxamideYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2,3,4,5,6-Pentafluorophenyl 4-(4-bromo-2-fluoroanilino)-1-methyl-6-oxo-1,6-dihydro-3-pyridinecarboxylate in THF was reacted with conc. NH3 solution as for example 37, step B. Recrystallisation (EtOAc/Hexane) yielded 4-(4-bromo-2-fluoroanilino)-1-methyl-6-oxo-1,6-dihydro-3-pyridinecarboxamide (100%); m.p. (EtOAc/Hexane) 282-284° C. 1H NMR [400 MHz, (CD3)2SO] δ 10.39 (s, 1H), 8.35 (s, 1H), 7.89 (br s, 1H), 7.66 (dd, J=10.4, 1.7 Hz, 1H), 7.51-7.44 (br m, 2H), 7.42 (dd, J=8.5, 1.9 Hz, 1H), 5.55 (s, 1H), 3.38 (s, 3H). LCMS (ACPI−) 340 (100%), 338 (90%). Anal. Calcd for C13H11BrFN3O2: C, 45.9; H, 3.3; N, 12.4. Found C, 46.1; H, 3.2; N, 12.6.

Workup

  1. customRecrystallisation (EtOAc/Hexane)

Sources & evidence

ORD record
ord-286cba12140c41c1a101469cd60935be
Source dataset
uspto-grants-2007_09
Patent number
US07273877B2

Reaction notes

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