Niclosamide → HCID 68760257, 화합물

HRID 1914488

반응식

HRID 1914488 반응식
[CH3:1][C:2]1([CH3:12])[O:6][C@H:5]([CH2:7][C:8]([OH:10])=[O:9])[C:4](=[O:11])[O:3]1.C(Cl)(=O)C(Cl)=O.CN(C)C=O.[Cl:24][C:25]1[CH:26]=[CH:27][C:28](O)=[C:29]([CH:43]=1)[C:30]([NH:32][C:33]1[CH:38]=[CH:37][C:36]([N+:39]([O-:41])=[O:40])=[CH:35][C:34]=1[Cl:42])=[O:31]>C(Cl)(Cl)Cl.N1C=CC=CC=1>[CH3:1][C:2]1([CH3:12])[O:6][C@H:5]([CH2:7][C:8]([O:10][C:28]2[CH:27]=[CH:26][C:25]([Cl:24])=[CH:43][C:29]=2[C:30](=[O:31])[NH:32][C:33]2[CH:38]=[CH:37][C:36]([N+:39]([O-:41])=[O:40])=[CH:35][C:34]=2[Cl:42])=[O:9])[C:4](=[O:11])[O:3]1

참가 물질

7

반응물 4

HCID 4477NiclosamideHCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 108449602-((4R)-2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl)acetic acid

생성물 1

HCID 68760257HCID 68760257, 화합물

시약·촉매·용매 2

HCID 1049Pyridine용매HCID 6212Chloroform용매

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온도
50 °C

실험 절차

A suspension of (R)-(−)-2,2-Dimethyl-5-oxo-1,3-dioxolane-4-acetic acid (Sigma-Aldrich, St. Louis, Mo.) (2.17 g, 12.46 mmol) in chloroform (24 mL) was treated with oxalyl chloride (2.11 mL, 25 mmol) and a drop of N,N-dimethylformamide was added. The progression of reaction was monitored by the observation of gas evolution by means of a bubbler. After 2 hours at room temperature, the reaction mixture was warmed to 50° C. for 2 hours, cooled to room temperature, and concentrated to remove volatiles. This residue was diluted with chloroform (10 mL) and added to a suspension of 5-Chloro-N-(2-chloro-4-nitrophenyl)-2-hydroxybenzamide (2.04 g, 6.23 mmol) in pyridine (30 mL) in which 4-dimethylaminopyride (20 mg) had been previously dissolved. The reaction mixture was stirred at room temperature for 16 h and then was partitioned between 1N aqueous HCl and ethyl acetate. The ethyl acetate solution was dried over magnesium sulfate and concentrated to a dark oil. The residue was dissolved in chloroform and placed upon a short column of silica gel (60 mm i.d.×15 mm). The product was eluted with chloroform and concentrated to an oil. The product was crystallized with a mixture of hexanes and ethyl acetate. 1HNMR (300 MHz, DMSO-d6): δ 1.456 (s, 3H), 1.495 (s, 3H), 4.939 (m, 1H), 7.352 (d, J=9 Hz, 1H, H3), 7.730 (dd, J=3.9 Hz, 1H, H4), 7.851 (d, J=3 Hz, 1H, H6), 8.110 (d, J=9 Hz, 1H, H6′), 8.255 (dd, J=3, 9 Hz, 1H, H5′), 8.411 (d, J=3 Hz, 1H, H3′), 10.481 (s, 1H, NH).

후처리

  1. customThe progression of reaction
  2. temperaturecooled to room temperature
  3. concentrationconcentrated
  4. customto remove volatiles
  5. additionThis residue was diluted with chloroform (10 mL)
  6. dissolutionhad been previously dissolved
  7. customwas partitioned between 1N aqueous HCl and ethyl acetate
  8. dry with materialThe ethyl acetate solution was dried over magnesium sulfate
  9. concentrationconcentrated to a dark oil
  10. dissolutionThe residue was dissolved in chloroform
  11. washThe product was eluted with chloroform
  12. concentrationconcentrated to an oil
  13. customThe product was crystallized with a mixture of hexanes and ethyl acetate

출처 및 근거

ORD 기록
ord-c5b4f695d6964a11bc18fa4d98a72df8
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08614205B2

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