4-Chloro-2-sulfanylbenzoic acid → tert-Butyl 2-[2-(7-chloro-4-oxo-4H-1,3-benzothiazin-2-yl)-4-pyridyl]ethylcarbamate

HRID 499488노트

반응식

HRID 499488 반응식
[C:1]([C:3]1[CH:8]=[C:7]([CH2:9][CH2:10][NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH:6]=[CH:5][N:4]=1)#[N:2].[Cl:19][C:20]1[CH:21]=[C:22]([SH:29])[C:23](=[CH:27][CH:28]=1)[C:24](O)=[O:25]>N1C=CC=CC=1>[Cl:19][C:20]1[CH:28]=[CH:27][C:23]2[C:24](=[O:25])[N:2]=[C:1]([C:3]3[CH:8]=[C:7]([CH2:9][CH2:10][NH:11][C:12](=[O:18])[O:13][C:14]([CH3:15])([CH3:17])[CH3:16])[CH:6]=[CH:5][N:4]=3)[S:29][C:22]=2[CH:21]=1

참가 물질

4

반응물 2

HCID 204569744-Chloro-2-sulfanylbenzoic acidHCID 22939273tert-Butyl 2-(2-cyano-4-pyridyl)ethylcarbamate

생성물 1

HCID 22939621tert-Butyl 2-[2-(7-chloro-4-oxo-4H-1,3-benzothiazin-2-yl)-4-pyridyl]ethylcarbamate수율 19.1%

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

tert-Butyl 2-(2-cyano-4-pyridyl)ethylcarbamate (1.5 g, 6.0 mmol) and 4-chlorothiosalicylic acid (2.3 g, 12.1 mmol) were dissolved in pyridine (10 ml), and the mixture was refluxed for 18 hrs. The solvent was evaporated, and the residue was subjected to a silica gel column chromatography. The fractions eluted with hexane-ethyl acetate (1:1, v/v) were collected, concentrated and recrystallized from hexane-tetrahydrofuran to give the titled compound (0.48 g, 19%) as white crystals.

후처리

  1. temperaturethe mixture was refluxed for 18 hrs
  2. customThe solvent was evaporated
  3. washThe fractions eluted with hexane-ethyl acetate (1:1
  4. customv/v) were collected
  5. concentrationconcentrated
  6. customrecrystallized from hexane-tetrahydrofuran

출처 및 근거

ORD 기록
ord-e6d9d706ce9442e89634ca7c0a95a1b9
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07767665B2

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