Sodium Iodide → 4-(4-(2-(4-(8-Quinolyl)piperazinyl)ethyl)phenyl)-2-aminothiazole

HRID 329401

반응식

HRID 329401 반응식
Br.Cl[CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:12]=[C:13]([NH2:16])[S:14][CH:15]=2)=[CH:7][CH:6]=1.[N:17]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][C:25]=2[N:27]2[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]2)[CH:20]=[CH:19][CH:18]=1.C(=O)([O-])[O-].[Na+].[Na+].[I-].[Na+]>C(OCC)(=O)C.O.C(O)C>[N:17]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][C:25]=2[N:27]2[CH2:28][CH2:29][N:30]([CH2:3][CH2:4][C:5]3[CH:10]=[CH:9][C:8]([C:11]4[N:12]=[C:13]([NH2:16])[S:14][CH:15]=4)=[CH:7][CH:6]=3)[CH2:31][CH2:32]2)[CH:20]=[CH:19][CH:18]=1

참가 물질

7

반응물 4

HCID 5238Sodium IodideHCID 10340Sodium CarbonateHCID 118307868-(1-piperazinyl)QuinolineHCID 147269834-(2-Chloroethyl)phenyl-2-aminothiazole hydrobromide

생성물 1

HCID 147270064-(4-(2-(4-(8-Quinolyl)piperazinyl)ethyl)phenyl)-2-aminothiazole

시약·촉매·용매 2

HCID 702Ethanol용매HCID 22728543Water ethylacetate용매

실험 절차

To a 35 ml round-bottomed flask equipped with condenser and N2 inlet were added 0.746 g (2.34 mmol) of 4-(4-(2-chloroethyl)phenyl-2-aminothiazole hydrobromide, 0.50 g (2.34 mmol) of N-(8-quinolyl)piperazine (prepared from 8-aminoquinoline by reaction with diethanolamine in hydrobromide at 200° C.), 0.621 g (5.86 mmol) of sodium carbonate, 50 mg of sodium iodide, and 10 ml of ethanol. The reaction was heated at reflux for 25 hours, cooled, and the reaction mixture taken up in ethyl acetate/water. The layers were separated, the ethyl acetate layer dried and evaporated. The residue was chromatographed on silica gel using chloroform/methanol as eluent and the product fractions combined in methanol and precipitated with a solution of hydrochloride in ether. The precipitate was stirred with ether/methanol to afford a crystalline solid, m.p. >225° C., 277 mg (27%). NMR (free base in CDCl3): 2.8 (m, 8H), 3.5 (m, 4H), 7.0-8.2 (m, 11H).

후처리

  1. customTo a 35 ml round-bottomed flask equipped with condenser and N2 inlet
  2. temperatureThe reaction was heated
  3. temperatureat reflux for 25 hours
  4. temperaturecooled
  5. customThe layers were separated
  6. dry with materialthe ethyl acetate layer dried
  7. customevaporated
  8. customThe residue was chromatographed on silica gel
  9. customprecipitated with a solution of hydrochloride in ether
  10. customto afford a crystalline solid, m.p. >225° C., 277 mg (27%)

출처 및 근거

ORD 기록
ord-73780695d59245b380b2a0822a066e6b
출처 데이터셋
uspto-grants-1990_01
특허 번호
US04891375

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