Ammonia → HCID 11818670, compound

HRID 917761Notes

Reaction equation

HRID 917761 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]([O:22]C2C(F)=C(F)C(F)=C(F)C=2F)=O)=[CH:3]1.[NH3:34]>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]([NH2:34])=[O:22])=[CH:3]1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 86596380HCID 86596380, compound

Product 1

HCID 11818670HCID 11818670, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2,3,4,5,6-Pentafluorophenyl 1-methyl-4-(2-naphthylamino)-6-oxo-1,6-dihydro-3-pyridinecarboxylate in THF was reacted with conc. NH3 solution as for example 37, step B. The crude product was recrystallised (MeOH/EtOAc) to give 1-methyl-4-(2-naphthylamino)-6-oxo-1,6-dihydro-3-pyridinecarboxamide as a white solid (87%); m.p. (MeOH/EtOAc) 254-257° C. 1H NMR [400 MHz, (CD3)2SO] δ 10.56 (s, 1H), 8.35 (s, 1H), 7.95-7.86 (m, 4H), 7.74 (d, J=1.9 Hz, 1H), 7.53-7.42 (m, 3H), 7.39 (dd, J=8.7, 2.1 Hz, 1H), 5.86 (s, 1H), 3.37 (s, 3H). LCMS (ACPI−) 292 (100%). Anal. Calcd for C17H15N3O2: C, 69.6; H, 5.2; N, 14.3. Found C, 69.4; H, 5.2; N, 14.5.

Workup

  1. customThe crude product was recrystallised (MeOH/EtOAc)

Sources & evidence

ORD record
ord-1475f3d702ba4c3a9895e7143408a8f2
Source dataset
uspto-grants-2007_09
Patent number
US07273877B2

Reaction notes

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