Dimethylamine → HCID 11269976, compound

HRID 917771Notes

Reaction equation

HRID 917771 reaction equation
[CH3:1][NH:2][CH3:3].[F:4][C:5]1[CH:33]=[C:32]([I:34])[CH:31]=[CH:30][C:6]=1[NH:7][C:8]1[C:9]([C:16]([O:18]C2C(F)=C(F)C(F)=C(F)C=2F)=O)=[CH:10][N:11]([CH3:15])[C:12](=[O:14])[CH:13]=1>C1COCC1>[F:4][C:5]1[CH:33]=[C:32]([I:34])[CH:31]=[CH:30][C:6]=1[NH:7][C:8]1[C:9]([C:16]([N:2]([CH3:3])[CH3:1])=[O:18])=[CH:10][N:11]([CH3:15])[C:12](=[O:14])[CH:13]=1

Participants

4

Reactant 2

HCID 674DimethylamineHCID 23631099HCID 23631099, compound

Product 1

HCID 11269976HCID 11269976, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Dimethylamine (40% in aqueous solution) was added to 2,3,4,5,6-pentafluorophenyl 4-(2-fluoro-4-iodoanilino)-1-methyl-6-oxo-1,6-dihydro-3-pyridinecarboxylate in THF as for example 37, step B, and the solution stirred at RT for 15 h. The resultant precipitate was removed by filtration and washed with hexane and Et2O. The filtrate was concentrated under reduced pressure and triturated with hexane to give 4-(2-fluoro-4-iodoanilino)-N,N,1-trimethyl-6-oxo-1,6-dihydro-3-pyridinecarboxamide as a pale yellow solid (58%); m.p. 106-111° C. (glue-liquid). 1H NMR [400 MHz, (CD3)2SO] δ 8.21 (s, 1H), 7.79 (s, 1H), 7.72 (dd, J=10.2, 1.9 Hz, 1H), 7.56 (dt, J=8.4, 1.2 Hz, 1H), 7.16 (t, J=8.4 Hz, 1H), 5.41 (d, J=1.2 Hz, 1H), 3.34 (s, 3H), 2.98 (s, 6H). HRMS (FAB+) calcd for C15H16FIN3O2 416.0271 (M+), found 416.0270. HPLC 97.2% (254 nm).

Workup

  1. customThe resultant precipitate was removed by filtration
  2. washwashed with hexane and Et2O
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customtriturated with hexane

Sources & evidence

ORD record
ord-26899204bbe040c6bbe83c4a5391fce4
Source dataset
uspto-grants-2007_09
Patent number
US07273877B2

Reaction notes

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