N-(4-chlorobenzyl)-7-methyl-2-(4-morpholinylmethyl)-4-oxo-4,7-dihydrothieno(2,3-b)pyridine-5-carboxamide → Thieno(2,3-b)pyridine-5-carboxamide, N-((4-chlorophenyl)methyl)-4,7-dihydro-7-methyl-2-(4-morpholinylmethyl)-4-oxo-, hydrochloride (1:1)

HRID 2299306Notes

Reaction equation

HRID 2299306 reaction equation
[Cl:1][C:2]1[CH:29]=[CH:28][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:11](=[O:27])[C:12]3[CH:19]=[C:18]([CH2:20][N:21]4[CH2:26][CH2:25][O:24][CH2:23][CH2:22]4)[S:17][C:13]=3[N:14]([CH3:16])[CH:15]=2)=[O:9])=[CH:4][CH:3]=1>Cl>[ClH:1].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:11](=[O:27])[C:12]3[CH:19]=[C:18]([CH2:20][N:21]4[CH2:22][CH2:23][O:24][CH2:25][CH2:26]4)[S:17][C:13]=3[N:14]([CH3:16])[CH:15]=2)=[O:9])=[CH:28][CH:29]=1

Participants

3

Reactant 1

HCID 503580N-(4-chlorobenzyl)-7-methyl-2-(4-morpholinylmethyl)-4-oxo-4,7-dihydrothieno(2,3-b)pyridine-5-carboxamide

Product 1

HCID 18380160Thieno(2,3-b)pyridine-5-carboxamide, N-((4-chlorophenyl)methyl)-4,7-dihydro-7-methyl-2-(4-morpholinylmethyl)-4-oxo-, hydrochloride (1:1)Yield 179.3%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

N-(4-chlorobenzyl)-7-methyl-2-(4-morpholinylmethyl)-4-oxo-4,7-dihydro-thieno[2,3-b]pyridine-5-carboxamide (1.50 g) from Example No. 36 is dissolved in methanolic HCl (50 mL) and concentrated in vacuo. The resulting off-white solid is recrystallized from methanol/ethanol to yield 1.458 g (90%) of the title compound as a white solid. Physical characteristics are as follows:

Workup

  1. concentrationconcentrated in vacuo
  2. customThe resulting off-white solid is recrystallized from methanol/ethanol

Sources & evidence

ORD record
ord-df221610b9cd49ada947e9d0dbd21160
Source dataset
uspto-grants-2002_12
Patent number
US06495683B2

Reaction notes

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