Trifluoromethanesulfonic anhydride → 1-(6-Bromo-7-trifluoromethylsulfonyl-2-benzothiazolyl)-3-ethylurea

HRID 9117

반응식

HRID 9117 반응식
[Br:1][C:2]1[CH:16]=[CH:15][C:5]2[N:6]=[C:7]([NH:9][C:10]([NH:12][CH2:13][CH3:14])=[O:11])[S:8][C:4]=2[C:3]=1O.[O:18](S(C(F)(F)F)(=O)=O)[S:19]([C:22]([F:25])([F:24])[F:23])(=O)=[O:20]>N1C=CC=CC=1>[Br:1][C:2]1[CH:16]=[CH:15][C:5]2[N:6]=[C:7]([NH:9][C:10]([NH:12][CH2:13][CH3:14])=[O:11])[S:8][C:4]=2[C:3]=1[S:19]([C:22]([F:25])([F:24])[F:23])(=[O:20])=[O:18]

참가 물질

4

반응물 2

HCID 67749Trifluoromethanesulfonic anhydrideHCID 219855951-(6-Bromo-7-hydroxy-2-benzothiazolyl)-3-ethylurea

생성물 1

HCID 219855071-(6-Bromo-7-trifluoromethylsulfonyl-2-benzothiazolyl)-3-ethylurea

시약·촉매·용매 1

HCID 1049Pyridine용매

반응 조건

온도
35 °C

실험 절차

To a solution of 1-(6-bromo-7-hydroxy-2-benzothiazolyl)-3-ethyl-urea (50 mg, 0.158 mmol) in pyridine (1 mL) were added 3 portions of (CF3SO2)2O (29 μL, 0.174 mmol) about 45 minutes apart. The reaction mixture was stirred for about 3 hours at about 35° C. The solvent was then evaporated. The crude material was purified by LC/MS to give 23 mg (32%) pure 14. 1H NMR (DMSO) δ 1.09 (t, 3H, J=8 Hz CH3), 3.19 (m, 2H, CH2), 6.79 (br s, 1H, NH), 7.67 (d, 1H, J=12 Hz, ArH), 7.80 (d, 1H, J=8 Hz, ArH), 11.20 (br s, 1H, NH). HPLC retention time 3.58 minutes.

후처리

  1. customThe solvent was then evaporated
  2. customThe crude material was purified by LC/MS
  3. customto give 23 mg (32%) pure 14

출처 및 근거

ORD 기록
ord-871ba8cd3b864435860dd69669537659
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07091227B2

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