2,4,6-Trimethylpyridine → N-(4-chlorobenzyl)-2-(chloromethyl)-7-propyl-4-oxo4,7-dihydrothieno[2,3-b]pyridine-5-carboxamide

HRID 2307295Notes

Reaction equation

HRID 2307295 reaction equation
N1C(C)=CC(C)=CC=1C.CS([Cl:14])(=O)=O.[Cl:15][C:16]1[CH:40]=[CH:39][C:19]([CH2:20][NH:21][C:22]([C:24]2[C:25](=[O:38])[C:26]3[CH:35]=[C:34]([CH2:36]O)[S:33][C:27]=3[N:28]([CH2:30][CH2:31][CH3:32])[CH:29]=2)=[O:23])=[CH:18][CH:17]=1>CN(C=O)C.O>[Cl:15][C:16]1[CH:40]=[CH:39][C:19]([CH2:20][NH:21][C:22]([C:24]2[C:25](=[O:38])[C:26]3[CH:35]=[C:34]([CH2:36][Cl:14])[S:33][C:27]=3[N:28]([CH2:30][CH2:31][CH3:32])[CH:29]=2)=[O:23])=[CH:18][CH:17]=1

Participants

6

Reactant 3

HCID 79532,4,6-TrimethylpyridineHCID 31297Methanesulfonyl chlorideHCID 22605728N-(4-chlorobenzyl)-7-propyl-2-(hydroxymethyl)-4-oxo-4,7-dihydrothieno[2,3-b]pyridine-5-carboxamide

Product 1

HCID 22605695N-(4-chlorobenzyl)-2-(chloromethyl)-7-propyl-4-oxo4,7-dihydrothieno[2,3-b]pyridine-5-carboxamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

4-N,N-Dimethylaminopyridine (80 mg), 2,4,6-collidine (1.39 mL), and methanesulfonyl chloride (0.81 mL) are added to a solution of N-(4-chlorobenzyl)-7-propyl-2-(hydroxymethyl)-4-oxo-4,7-dihydrothieno[2,3-b]pyridine-5-carboxamide (Preparation 12, 1.63 g) in anhydrous DMF (80 mL). The reaction mixture is stirred at room temperature for 24 h. The mixture is diluted with water (150 mL) and filtered. The resulting light yellow powder is recrystallized from acetonitrile and dried in a vacuum oven to afford 1.4 g of the title compound as a light yellow solid. Physical characteristics. Mp 186.5-188° C.; 1H NMR (300 Mhz,7 DMSO-6) δ 10.45, 8.75, 7.56, 7.39, 5.15, 4.54, 4.27, 1.85, 0.91. Anal. Found: C, 55.76; H, 4.59; N, 6.95; Cl, 16.88; S, 7.80.

Workup

  1. filtrationfiltered
  2. customThe resulting light yellow powder is recrystallized from acetonitrile
  3. customdried in a vacuum oven

Sources & evidence

ORD record
ord-c5f816fcff8b429c87a50de413586b84
Source dataset
uspto-grants-2004_12
Patent number
US06831081B2

Reaction notes

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