Sulfathiazole → Succinylsulfathiazole

HRID 16654

반응식

HRID 16654 반응식
[C:1]1(=[O:7])[O:6][C:4](=[O:5])[CH2:3][CH2:2]1.[CH:8]1[C:13]([NH2:14])=[CH:12][CH:11]=[C:10]([S:15]([NH:18][C:19]2[S:23][CH:22]=[CH:21][N:20]=2)(=[O:17])=[O:16])[CH:9]=1.C(N(CC)CC)C>O1CCCC1>[CH:12]1[C:13]([NH:14][C:1]([CH2:2][CH2:3][C:4]([OH:6])=[O:5])=[O:7])=[CH:8][CH:9]=[C:10]([S:15]([NH:18][C:19]2[S:23][CH:22]=[CH:21][N:20]=2)(=[O:17])=[O:16])[CH:11]=1

참가 물질

5

반응물 3

HCID 5340SulfathiazoleHCID 7922Succinic anhydrideHCID 8471Triethylamine

생성물 1

HCID 5315Succinylsulfathiazole수율 67%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

an Indo-Sulfathiazole Analog: Compound 27j was synthesized by the method outlined in FIG. 1. Briefly, Compound 27j was synthesized by first complexing succinic anhydride with sulfathiazole by reacting these compounds at room temperature for 6 hours in tetrahydrofuran (THF) in the presence of triethylamine (TEA) to produce succinylsulfathiazole as a white solid (67% yield). The succinylsulfathiazole was then reacted for 2 hours at room temperature with O—(N-succinimidyl)-1,1,3,3-tetramethyluronium tetrafluoroborate (TSTU) in dichloromethane in the presence of TEA to produce the corresponding succinimidyl ester, which was reacted with 1-(4-aminobutyl)-2-{1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl}acetamide in dichloromethane in the presence of TEA at room temperature for 16 hours to produce Compound 27j as a yellow gummy mass (45% yield). Compound 27j was characterized by NMR, two-dimensional NMR, and mass spectroscopy.

후처리

  1. customat room temperature
  2. customfor 6 hours

출처 및 근거

ORD 기록
ord-188dcdf9ff0941fd9334d21b814bbcc3
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07736624B2

연결된 노트

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