Methanol → 1-(6-Bromo-7-benzyloxy-2-benzothiazolyl)-3-ethyl-urea

HRID 9112

반응식

HRID 9112 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]=1[OH:17].C(=O)([O-])[O-].[K+].[K+].[CH2:24](Br)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.CO>CN(C=O)C>[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[O:17][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

참가 물질

6

반응물 4

HCID 887MethanolHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 219855951-(6-Bromo-7-hydroxy-2-benzothiazolyl)-3-ethylurea

생성물 1

HCID 219856041-(6-Bromo-7-benzyloxy-2-benzothiazolyl)-3-ethyl-urea수율 45%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
20 °C

실험 절차

A mixture of 1-(6-bromo-7-hydroxy-2-benzothiazolyl)-3-ethyl-urea 6 (0.050 g, 0.16 mmol) and potassium carbonate (0.023 g, 0.17 mmol, 1.05 eq) in anhydrous DMF (1.6 mL) was stirred at about 20° C. for about 0.5 hour, and was cooled down to about 0° C. The reaction mixture was treated with benzyl bromide (0.019 mL, 0.16 mmol, 1.0 eq), and was stirred at about 0° C. for about 16 hours. To the reaction mixture was added methanol (10 mL). The solid was filtered off and rinsed with methanol (3 mL). The solvent was evaporated and the residue was dissolved in DMF (2 mL). The crude reaction solution was purified by LC/MS to give 0.029 g (45%) of the desired compound 9. 1H NMR (DMSO) δ 10.86 (br s, 1H, NH), 7.59–7.34 (m, 7H, ArH), 6.72 (br s, 1H, NH), 5.17 (s, 2H, CH2), 3.18 (m, 2H, CH2), 1.09 (t, 3H, J=7.2 Hz, CH3); LC/MS 406 (MH+); RP-HPLC RT 3.8 minutes.

후처리

  1. temperaturewas cooled down to about 0° C
  2. stirringwas stirred at about 0° C. for about 16 hours
  3. filtrationThe solid was filtered off
  4. washrinsed with methanol (3 mL)
  5. customThe solvent was evaporated
  6. dissolutionthe residue was dissolved in DMF (2 mL)
  7. customThe crude reaction solution
  8. customwas purified by LC/MS

출처 및 근거

ORD 기록
ord-c5baa1466eb64f28875bdeda9757c685
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07091227B2

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