(E)-N-(3-fluorobenzyl)-4-methyl-6-morpholino-2-(prop-1-enyl)-pyridine-3-carboxylic acid amide → N-[(3-fluorophenyl)-methyl]-4-methyl-6-morpholin-4-yl-2-propyl-pyridine-3-carboxylic acid amide

HRID 1039748Notes

Reaction equation

HRID 1039748 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:25]=[CH:26][CH:27]=1)[CH2:5][NH:6][C:7]([C:9]1[C:10](/[CH:22]=[CH:23]/[CH3:24])=[N:11][C:12]([N:16]2[CH2:21][CH2:20][O:19][CH2:18][CH2:17]2)=[CH:13][C:14]=1[CH3:15])=[O:8]>CO.[Pd]>[F:1][C:2]1[CH:3]=[C:4]([CH2:5][NH:6][C:7]([C:9]2[C:10]([CH2:22][CH2:23][CH3:24])=[N:11][C:12]([N:16]3[CH2:21][CH2:20][O:19][CH2:18][CH2:17]3)=[CH:13][C:14]=2[CH3:15])=[O:8])[CH:25]=[CH:26][CH:27]=1

Participants

4

Reactant 1

HCID 67287461(E)-N-(3-fluorobenzyl)-4-methyl-6-morpholino-2-(prop-1-enyl)-pyridine-3-carboxylic acid amide

Product 1

HCID 67286956N-[(3-fluorophenyl)-methyl]-4-methyl-6-morpholin-4-yl-2-propyl-pyridine-3-carboxylic acid amideYield 61.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 300 mg (0.81 mmol) (E)-N-(3-fluorobenzyl)-4-methyl-6-morpholino-2-(prop-1-enyl)-pyridine-3-carboxylic acid amide (example 9) in MeOH (9 ml) was degassed with argon for 15 min. Then 0.065 g Pd/C (10% w/w) was added and the RM was stirred for 3 h under hydrogen atmosphere by use of an H2 balloon. Subsequently the mixture was filtered through celite and the filtrate was concentrated in vacuo. Purification of the residue by CC (hexane/acetone 17:3) provided 170 mg (0.5 mmol, 56%) N-[(3-fluorophenyl)-methyl]-4-methyl-6-morpholin-4-yl-2-propyl-pyridine-3-carboxylic acid amide (example 10). [M+H]+ 372.2.

Workup

  1. filtrationSubsequently the mixture was filtered through celite
  2. concentrationthe filtrate was concentrated in vacuo
  3. customPurification of the residue by CC (hexane/acetone 17:3)

Sources & evidence

ORD record
ord-14c635f87a674ffe8e133f647afcdf1e
Source dataset
uspto-grants-2013_10
Patent number
US08552200B2

Reaction notes

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