Ethyl Acetate → 4-tert.-butyl-N-{6-[2-(ethanesulfonyl-methyl-amino)-ethoxy]-5-p-tolyl-pyrimidin-4-yl}-benzenesulfonamide

HRID 1358319노트

반응식

HRID 1358319 반응식
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:14][C:15]2[C:20]([C:21]3[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=3)=[C:19](Cl)[N:18]=[CH:17][N:16]=2)(=[O:13])=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[OH:29][CH2:30][CH2:31][N:32]([CH3:38])[S:33]([CH2:36][CH3:37])(=[O:35])=[O:34].C(OCC)(=O)C>C1COCC1>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:14][C:15]2[C:20]([C:21]3[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=3)=[C:19]([O:29][CH2:30][CH2:31][N:32]([S:33]([CH2:36][CH3:37])(=[O:35])=[O:34])[CH3:38])[N:18]=[CH:17][N:16]=2)(=[O:13])=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

참가 물질

5

반응물 3

HCID 8857Ethyl AcetateHCID 18184242N-(2-hydroxyethyl)-N-methyl-ethanesulfonamideHCID 227294154-tert.-butyl-N-[6-chloro-5-(p-tolyl)4-pyrimidinyl]-benzene sulfonamide

생성물 1

HCID 867590734-tert.-butyl-N-{6-[2-(ethanesulfonyl-methyl-amino)-ethoxy]-5-p-tolyl-pyrimidin-4-yl}-benzenesulfonamide수율 34.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

100 mg 4-tert.-butyl-N-[6-chloro-5-(p-tolyl)-4-pyrimidinyl]-benzene sulfonamide was dissolved in 5 ml dry THF. 162 mg of potassium-tert.-butylate and 200 mg of N-(2-hydroxyethyl)-N-methyl-ethanesulfonamide was added and the mixture was heated to reflux for 8 h then cooled to room temperature. Ethyl acetate was added and the precipitated side product was filtered off. The filtrate was concentrated in vacuo. The crude product was purified by column chromatography (silica gel; ethyl acetate) to give 45 mg of 4-tert.-butyl-N-{6-[2-(ethanesulfonyl-methyl-amino)-ethoxy]-5-p-tolyl-pyrimidin-4-yl}-benzenesulfonamide. LC-MS: tR=5.58 min, [M−1]−=545.54.

후처리

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 8 h
  3. filtrationthe precipitated side product was filtered off
  4. concentrationThe filtrate was concentrated in vacuo
  5. customThe crude product was purified by column chromatography (silica gel; ethyl acetate)

출처 및 근거

ORD 기록
ord-514d1b28a69341c28f41b8bd3ee2e984
출처 데이터셋
uspto-grants-2003_07
특허 번호
US06596719B1

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