N-[(4-chlorophenyl)methyl]-7-ethyl-2-(3-hydroxyprop-1-ynyl)-4-oxo-thieno[2,3-b]pyridine-5-carboxamide → N-[(4-chlorophenyl)methyl]-7-ethyl-2-(3-hydroxypropyl)-4-oxo-thieno[2,3-b]pyridine-5-carboxamide
Reaction equation
[Cl:1][C:2]1[CH:27]=[CH:26][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:11](=[O:25])[C:12]3[CH:20]=[C:19]([C:21]#[C:22][CH2:23][OH:24])[S:18][C:13]=3[N:14]([CH2:16][CH3:17])[CH:15]=2)=[O:9])=[CH:4][CH:3]=1>[Pd].C(Cl)Cl.CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:11](=[O:25])[C:12]3[CH:20]=[C:19]([CH2:21][CH2:22][CH2:23][OH:24])[S:18][C:13]=3[N:14]([CH2:16][CH3:17])[CH:15]=2)=[O:9])=[CH:26][CH:27]=1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
A solution of N-(4-chlorobenzyl)-7-ethyl-2-(3-hydroxy-1-propynyl)-4-oxo-4,7-dihydrothieno[2,3-b]pyridine-5-carboxamide (Example No. 14) (0.197 g) in 1/1 CH2Cl2/CH3OH (50 mL) is hydrogenated over 10% Pd/C (59 mg) at 35 psi for 2 h. The reaction mixture is filtered through a Celite pad, and the filtrate is concentrated in vacuo. The resulting yellow solid is purified via column chromatography (CH2Cl2, CH2Cl2:CH3OH; 98:2, 95:5). Fractions homogeneous by TLC are combined and concentrated in vacuo to yield 0.114 g (57%) of the title compound as a white solid.
Workup
- filtrationThe reaction mixture is filtered through a Celite pad
- concentrationthe filtrate is concentrated in vacuo
- customThe resulting yellow solid is purified via column chromatography (CH2Cl2, CH2Cl2:CH3OH; 98:2, 95:5)
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-4e5a8e5c24ae4363b164e4f8c18b50b6
- Source dataset
- uspto-grants-2001_05
- Patent number
- US06239142B1
Reaction notes
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