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

HRID 2307295노트

반응식

HRID 2307295 반응식
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

참가 물질

6

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-c5f816fcff8b429c87a50de413586b84
출처 데이터셋
uspto-grants-2004_12
특허 번호
US06831081B2

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