HCID 11199166, compound → 4-[2-fluoro-4-(3-hydroxypropyl)anilino]-N-(2-hydroxyethyl)-1-methyl-6-oxo-1,6-dihydro-3-pyridinecarboxamide

HRID 917703Notes

Reaction equation

HRID 917703 reaction equation
[F:1][C:2]1[CH:22]=[C:21]([C:23]#[C:24][CH2:25][OH:26])[CH:20]=[CH:19][C:3]=1[NH:4][C:5]1[C:6]([C:13]([NH:15][CH2:16][CH2:17][OH:18])=[O:14])=[CH:7][N:8]([CH3:12])[C:9](=[O:11])[CH:10]=1>CO.[Pd]>[F:1][C:2]1[CH:22]=[C:21]([CH2:23][CH2:24][CH2:25][OH:26])[CH:20]=[CH:19][C:3]=1[NH:4][C:5]1[C:6]([C:13]([NH:15][CH2:16][CH2:17][OH:18])=[O:14])=[CH:7][N:8]([CH3:12])[C:9](=[O:11])[CH:10]=1

Participants

4

Reactant 1

HCID 11199166HCID 11199166, compound

Product 1

HCID 111992794-[2-fluoro-4-(3-hydroxypropyl)anilino]-N-(2-hydroxyethyl)-1-methyl-6-oxo-1,6-dihydro-3-pyridinecarboxamideYield 92%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

4-[2-Fluoro-4-(3-hydroxy-1-propynyl)anilino]-N-(2-hydroxyethyl)-1-methyl-6-oxo-1,6-dihydro-3-pyridinecarboxamide was hydrogenated in MeOH 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 (5% MeOH/CH2Cl2 as eluant) to give 4-[2-fluoro-4-(3-hydroxypropyl)anilino]-N-(2-hydroxyethyl)-1-methyl-6-oxo-1,6-dihydro-3-pyridinecarboxamide as a white solid (92%), m.p. (CH2Cl2/MeOH) 177-179° C. 1H NMR [(CD3)2SO, 400 MHz] δ 9.88 (s, 1H), 8.40 (br t, J=5.2 Hz, 1H), 8.26 (s, 1H), 7.33 (t, J=8.4 Hz, 1H), 7.17 (dd, J=11.8, 1.4 Hz, 1H), 7.06 (dd, J=8.2, 1.2 Hz, 1H), 5.42 (d, J=0.8 Hz, 1H), 4.78 (t, J=5.5 Hz, 1H), 4.49 (t, J=5.1 Hz, 1H), 3.50 (q, J=5.8 Hz, 2H), 3.41 (q, J=6.0 Hz, 2H), 3.35 (s, 3H), 3.31-3.25 (m, 2H), 2.63 (t, J=7.6 Hz, 2H), 1.72 (pentet, J=6.5 Hz, 2H). Anal. Calcd for C18H22FN3O4: C, 59.5; H, 6.1; N, 11.6. Found: C, 59.3; H, 6.3; N, 11.5.

Workup

  1. customPurification of the crude oil

Sources & evidence

ORD record
ord-d6273f51f0c84d92be6c2f463477d2db
Source dataset
uspto-grants-2007_09
Patent number
US07273877B2

Reaction notes

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