Succinic anhydride → HCID 10436069, compound

HRID 2299302Notes

Reaction equation

HRID 2299302 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.[C:28]1(=[O:34])[O:33][C:31](=[O:32])[CH2:30][CH2:29]1>N1C=CC=CC=1>[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]([C:21]#[C:22][CH2:23][O:24][C:28](=[O:34])[CH2:29][CH2:30][C:31]([OH:33])=[O:32])[S:18][C:13]=3[N:14]([CH2:16][CH3:17])[CH:15]=2)=[O:9])=[CH:26][CH:27]=1

Participants

4

Reactant 2

HCID 7922Succinic anhydrideHCID 6483693N-[(4-chlorophenyl)methyl]-7-ethyl-2-(3-hydroxyprop-1-ynyl)-4-oxo-thieno[2,3-b]pyridine-5-carboxamide

Product 1

HCID 10436069HCID 10436069, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To 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) (0.200 g) in pyridine (10 mL) is added succinic anhydride (0.639 g). The reaction is stirred at rt for 18 h then at 40° C. for 1 h. The reaction mixture is concentrated in vacuo. The residue is suspended in H2O (25 mL) and stirred for 1 h. An off-white solid is filtered off and recrystallized from ethanol to yield 0.210 g (84%) of the title compound as a pale yellow, crystalline solid.

Workup

  1. waitat 40° C. for 1 h
  2. concentrationThe reaction mixture is concentrated in vacuo
  3. stirringstirred for 1 h
  4. filtrationAn off-white solid is filtered off
  5. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-c0026fef089b4991a233e8163742d0fa
Source dataset
uspto-grants-2002_12
Patent number
US06495683B2

Reaction notes

Loading…