HCID 11221175, compound → HCID 11473059, compound

HRID 917713Notes

Reaction equation

HRID 917713 reaction equation
[C:1]([C:3]1[CH:23]=[CH:22][C:6]([NH:7][C:8]2[C:9]([C:15]([NH:17][CH2:18][CH2:19][CH2:20][OH:21])=[O:16])=[CH:10][NH:11][C:12](=[O:14])[CH:13]=2)=[C:5]([F:24])[CH:4]=1)#[CH:2]>CO.C1COCC1.[Pd]>[CH2:1]([C:3]1[CH:23]=[CH:22][C:6]([NH:7][C:8]2[C:9]([C:15]([NH:17][CH2:18][CH2:19][CH2:20][OH:21])=[O:16])=[CH:10][NH:11][C:12](=[O:14])[CH:13]=2)=[C:5]([F:24])[CH:4]=1)[CH3:2]

Participants

4

Reactant 1

HCID 11221175HCID 11221175, compound

Product 1

HCID 11473059HCID 11473059, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

4-(4-Ethynyl-2-fluoroanilino)-N-(3-hydroxypropyl)-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-(3-hydroxypropyl)-6-oxo-1,6-dihydro-3-pyridinecarboxamide as a white solid (91%), m.p. (EtOAc) 231-233° C. 1H NMR [(CD3)2SO, 400 MHz] δ 11.28 (br s, 1H), 10.02 (s, 1H), 8.41 (t, J=5.1 Hz, 1H), 7.90 (s, 1H), 7.32 (t, J=8.3 Hz, 1H), 7.19 (dd, J=11.9, 1.8 Hz, 1H), 7.08 (d, J=8.2 Hz, 1H), 5.33 (s, 1H), 4.44 (t, J=5.1 Hz, 1H), 3.46 (q, J=5.2 Hz, 2H), 3.30-3.22 (m, 2H), 2.62 (q, J=7.6 Hz, 2H), 1.66 (pentet, J=6.7 Hz, 2H), 1.21 (t, J=7.6 Hz, 3H). Anal. Calcd for C17H20FN3O3: C, 61.1; H, 6.1; N, 12.6. Found: C, 61.3; H, 5.9; N, 12.7.

Workup

  1. customPurification of the crude oil

Sources & evidence

ORD record
ord-cee0652537354cbca6da626b0c8120cd
Source dataset
uspto-grants-2007_09
Patent number
US07273877B2

Reaction notes

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