HCID 11186126, compound → HCID 11393001, compound

HRID 917710Notes

Reaction equation

HRID 917710 reaction equation
[C:1]([C:3]1[CH:22]=[CH:21][C:6]([NH:7][C:8]2[C:9]([C:15]([NH:17][CH2:18][CH2:19][OH:20])=[O:16])=[CH:10][NH:11][C:12](=[O:14])[CH:13]=2)=[C:5]([F:23])[CH:4]=1)#[CH:2]>CO.C1COCC1.[Pd]>[CH2:1]([C:3]1[CH:22]=[CH:21][C:6]([NH:7][C:8]2[C:9]([C:15]([NH:17][CH2:18][CH2:19][OH:20])=[O:16])=[CH:10][NH:11][C:12](=[O:14])[CH:13]=2)=[C:5]([F:23])[CH:4]=1)[CH3:2]

Participants

4

Reactant 1

HCID 11186126HCID 11186126, compound

Product 1

HCID 11393001HCID 11393001, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

4-(4-Ethynyl-2-fluoroanilino)-N-(2-hydroxyethyl)-6-oxo-1,6-dihydro-3-pyridinecarboxamide was hydrogenated in MeOH/THF in the presence of 5% Pd/C as for example 3. Purification of the crude oil was carried out by column chromatography on silica gel (10% MeOH/CH2Cl2 as eluant) to give 4-(4-ethyl-2-fluoroanilino)-N-(2-hydroxyethyl)-6-oxo-1,6-dihydro-3-pyridinecarboxamide as a white solid (100%), m.p. (EtOAc/MeOH) 256-258° C. 1H NMR [(CD3)2SO, 400 MHz] δ 11.29 (br s, 1H), 10.00 (s, 1H), 8.43 (t, J=5.2 Hz, 1H), 7.93 (s, 1H), 7.33 (t, J=8.4 Hz, 1H), 7.19 (dd, J=11.9, 1.5 Hz, 1H), 7.08 (dd, J=8.2, 1.5 Hz, 1H), 5.32 (s, 1H), 4.71 (t, J=5.7 Hz, 1H), 3.49 (q, J=5.9 Hz, 2H), 3.29-3.24 (m, 2H), 2.62 (q, J=7.6 Hz, 2H), 1.21 (t, J=7.6 Hz, 3H). Anal. Calcd for C16H18FN3O3: C, 60.2; H, 5.7; N, 13.2. Found: C, 60.2; H, 5.7; N, 13.4.

Workup

  1. customPurification of the crude oil

Sources & evidence

ORD record
ord-e5bdf719b6c440e5824070986a6a5a6b
Source dataset
uspto-grants-2007_09
Patent number
US07273877B2

Reaction notes

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