4-[2-fluoro-4-(3-hydroxy-1-propynyl)anilino]-N-(3-hydroxypropyl)-1-methyl-6-oxo-1,6-dihydro-3-pyridinecarboxamide → 4-[2-fluoro-4-(3-hydroxypropyl)anilino]-N-(3-hydroxypropyl)-1-methyl-6-oxo-1,6-dihydro-3-pyridinecarboxamide

HRID 917705Notes

Reaction equation

HRID 917705 reaction equation
[F:1][C:2]1[CH:23]=[C:22]([C:24]#[C:25][CH2:26][OH:27])[CH:21]=[CH:20][C:3]=1[NH:4][C:5]1[C:6]([C:13]([NH:15][CH2:16][CH2:17][CH2:18][OH:19])=[O:14])=[CH:7][N:8]([CH3:12])[C:9](=[O:11])[CH:10]=1>CO.[Pd]>[F:1][C:2]1[CH:23]=[C:22]([CH2:24][CH2:25][CH2:26][OH:27])[CH:21]=[CH:20][C:3]=1[NH:4][C:5]1[C:6]([C:13]([NH:15][CH2:16][CH2:17][CH2:18][OH:19])=[O:14])=[CH:7][N:8]([CH3:12])[C:9](=[O:11])[CH:10]=1

Participants

4

Reactant 1

HCID 112341384-[2-fluoro-4-(3-hydroxy-1-propynyl)anilino]-N-(3-hydroxypropyl)-1-methyl-6-oxo-1,6-dihydro-3-pyridinecarboxamide

Product 1

HCID 114288564-[2-fluoro-4-(3-hydroxypropyl)anilino]-N-(3-hydroxypropyl)-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-(3-hydroxypropyl)-1-methyl-6-oxo-1,6-dihydro-3-pyridinecarboxamide was hydrogenated in MeOH in the presence of 5% Pd/C 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-(3-hydroxypropyl)-1-methyl-6-oxo-1,6-dihydro-3-pyridinecarboxamide as a white solid (92%), m.p. (CH2Cl2/MeOH) 161-164° C. 1H NMR [(CD3)2SO, 400 MHz] δ 9.88 (s, 1H), 8.36 (t, J=5.4 Hz, 1H), 8.21 (s, 1H), 7.33 (t, J=8.3 Hz, 1H), 7.17 (dd, J=11.9, 1.7 Hz, 1H), 7.06 (dd, J=8.1, 1.4 Hz, 1H), 5.42 (d, J=0.9 Hz, 1H), 4.48 (t, J=5.0 Hz, 1H), 4.09 (q, J=5.2 Hz, 1H), 3.47 (q, J=5.9 Hz, 2H), 3.41 (q, J=6.0 Hz, 2H), 3.35 (s, 3H), 3.26 (q, J=6.6 Hz, 2H), 2.62 (t, J=7.7 Hz, 2H), 1.75-1.62 (m, 4H). Anal. Calcd for C19H24FN3O4.0.5H2O; C, 59.1; H, 6.5; N, 10.9. Found: C, 59.3; H, 6.4; N, 10.9.

Workup

  1. customPurification of the crude oil

Sources & evidence

ORD record
ord-652f6ea40f8444bf90a13e4bceb1fcea
Source dataset
uspto-grants-2007_09
Patent number
US07273877B2

Reaction notes

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