HCID 11403394, compound → HCID 11437715, compound

HRID 917716Notes

Reaction equation

HRID 917716 reaction equation
[C:1]([C:3]1[CH:20]=[CH:19][C:6]([NH:7][C:8]2[C:9]([C:16]([NH2:18])=[O:17])=[CH:10][N:11]([CH3:15])[C:12](=[O:14])[CH:13]=2)=[C:5]([F:21])[CH:4]=1)#[CH:2]>CO.C1COCC1.[Pd]>[CH2:1]([C:3]1[CH:20]=[CH:19][C:6]([NH:7][C:8]2[C:9]([C:16]([NH2:18])=[O:17])=[CH:10][N:11]([CH3:15])[C:12](=[O:14])[CH:13]=2)=[C:5]([F:21])[CH:4]=1)[CH3:2]

Participants

4

Reactant 1

HCID 11403394HCID 11403394, compound

Product 1

HCID 11437715HCID 11437715, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

4-(4-Ethynyl-2-fluoroanilino)-1-methyl-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 (50% acetone/CH2Cl2 as eluant) to give 4-(4-ethyl-2-fluoroanilino)-1-methyl-6-oxo-1,6-dihydro-3-pyridinecarboxamide as a cream solid (82%), m.p. (EtOAc) 268-272° C. 1H NMR [(CD3)2SO, 400 MHz] δ 10.14 (s, 1H), 8.32 (s, 1H), 7.84 (br s, 1H), 7.43 (br s, 1H), 7.33 (t, J=8.4 Hz, 1H), 7.19 (dd, J=11.1, 1.7 Hz, 1H), 7.08 (dd, J=8.2, 1.5 Hz, 1H), 5.39 (d, J=1.1 Hz, 1H), 3.36 (s, 3H), 2.62 (q, J=7.6 Hz, 2H), 1.19 (t, J=7.6 Hz, 3H). Anal. Calcd for C15H16FN3O2: C, 62.3; H, 5.6; N, 14.5. Found: C, 62.5; H, 5.4; N, 14.8.

Workup

  1. customPurification of the crude oil

Sources & evidence

ORD record
ord-008d25876347426d83a786cb5dabc432
Source dataset
uspto-grants-2007_09
Patent number
US07273877B2

Reaction notes

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