Pyridine → HCID 86596380, compound

HRID 917760Notes

Reaction equation

HRID 917760 reaction equation
[CH3:1][N:2]1[C:7](=[O:8])[CH:6]=[C:5]([NH:9][C:10]2[CH:19]=[CH:18][C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH:11]=2)[C:4]([C:20]([OH:22])=[O:21])=[CH:3]1.FC(F)(F)C(O[C:28]1[C:33]([F:34])=[C:32]([F:35])[C:31]([F:36])=[C:30]([F:37])[C:29]=1[F:38])=O.N1C=CC=CC=1>C1COCC1>[CH3:1][N:2]1[C:7](=[O:8])[CH:6]=[C:5]([NH:9][C:10]2[CH:19]=[CH:18][C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH:11]=2)[C:4]([C:20]([O:22][C:28]2[C:29]([F:38])=[C:30]([F:37])[C:31]([F:36])=[C:32]([F:35])[C:33]=2[F:34])=[O:21])=[CH:3]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 4327891Pentafluorophenyl TrifluoroacetateHCID 23630799HCID 23630799, compound

Product 1

HCID 86596380HCID 86596380, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-Methyl-4-(2-naphthylamino)-6-oxo-1,6-dihydro-3-pyridinecarboxylic acid and pentafluorophenyl trifluoroacetate were reacted in the presence of pyridine in THF as for example 4, step A. The crude residue was purified by flash chromatography on silica gel (60% EtOAc/Hexane) to give 2,3,4,5,6-pentafluorophenyl 1-methyl-4-(2-naphthylamino)-6-oxo-1,6-dihydro-3-pyridinecarboxylate (97%). 1H NMR [400 MHz, (CD3)2SO]δ 9.06 (s, 1H), 8.97 (s, 1H), 7.98 (d, J=8.8 Hz, 1H), 7.92 (t, J=9.0 Hz, 2H), 7.85 (d, J=1.9 Hz, 1H), 7.56-7.46 (m, 3H), 5.73 (s, 1H), 3.51 (s, 3H).

Workup

  1. customThe crude residue was purified by flash chromatography on silica gel (60% EtOAc/Hexane)

Sources & evidence

ORD record
ord-a074fd998c5d4dcc8100ab6915e5f88a
Source dataset
uspto-grants-2007_09
Patent number
US07273877B2

Reaction notes

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