Sodium Hydroxide → 1-(3-Cyanopropyl)-4-(2-fluoro-4-iodoanilino)-6-oxo-1,6-dihydro-3-pyridinecarboxylic acid

HRID 917728Notes

Reaction equation

HRID 917728 reaction equation
[C:1]([CH2:3][CH2:4][CH2:5][N:6]1[C:11](=[O:12])[CH:10]=[C:9]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([I:20])=[CH:16][C:15]=2[F:21])[C:8]([C:22]([O:24]CC)=[O:23])=[CH:7]1)#[N:2].[OH-].[Na+]>CCO>[C:1]([CH2:3][CH2:4][CH2:5][N:6]1[C:11](=[O:12])[CH:10]=[C:9]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([I:20])=[CH:16][C:15]=2[F:21])[C:8]([C:22]([OH:24])=[O:23])=[CH:7]1)#[N:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 23630802Ethyl 1-(3-cyanopropyl)-4-(2-fluoro-4-iodoanilino)-6-oxo-1,6-dihydro-3-pyridinecarboxylate

Product 1

HCID 589628511-(3-Cyanopropyl)-4-(2-fluoro-4-iodoanilino)-6-oxo-1,6-dihydro-3-pyridinecarboxylic acidYield 100%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 1-(3-cyanopropyl)-4-(2-fluoro-4-iodoanilino)-6-oxo-1,6-dihydro-3-pyridinecarboxylate was dissolved in EtOH and treated with 1 M NaOH, as for example 1, step C, to hydrolyse the ester to give 1-(3-cyanopropyl)-4-(2-fluoro-4-iodoanilino)-6-oxo-1,6-dihydro-3-pyridinecarboxylic acid as a white solid (100%), used directly in the next step. 1H NMR [(CD3)2SO, 400 MHz] δ 13.10 (v br s, 1H), 9.72 (br s, 1H), 8.48 (s, 1H), 7.76 (dd, J=10.1, 1.9 Hz, 1H), 7.60 (dd, J=8.4, 0.9 Hz, 1H), 7.30 (t, J=8.5 Hz, 1H), 5.49 (s, 1H), 3.95 (t, J=7.1 Hz, 2H), 2.52 (t, J=7.2 Hz, 2H), 1.93 (pentet, J=7.2 Hz, 2H). HRMS (FAB+) calcd C16H14FIN3O3 (MH+) 442.0064, found 442.0060.

Sources & evidence

ORD record
ord-11cef488e88b48f4a800b62bb3e6d294
Source dataset
uspto-grants-2007_09
Patent number
US07273877B2

Reaction notes

Loading…