Triethylamine → HCID 178484369, 화합물

HRID 1075678

반응식

HRID 1075678 반응식
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2=[CH:12][C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[N:16]=[CH:15][CH:14]=1.C(N(CC)CC)C.C(OC([NH:37][C:38]([N:40]([CH3:42])[CH3:41])=S)=O)(C)(C)C.C(OCC)(=O)C>CN(C=O)C.FC(F)(F)C(O)=O.Cl[Hg]Cl>[CH3:41][N:40]([CH3:42])[C:38](=[NH:37])[NH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2=[CH:12][C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[N:16]=[CH:15][CH:14]=1

참가 물질

8

반응물 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 450920251-t-Butoxycarbonyl-3,3-dimethylthioureaHCID 545367025-Amino-3-(quinol-4-ylmethylene)-2-oxindole

생성물 1

HCID 178484369HCID 178484369, 화합물수율 50%

시약·촉매·용매 3

HCID 24085Mercuric Chloride촉매HCID 6228Dimethylformamide용매HCID 6422Trifluoroacetic acid용매

실험 절차

To a solution of 5-amino-3-(4-quinolylmethylen) -2-oxindole (431 mg, 1.5 mmol) in DMF (100 ml) containing triethylamine (202 mg, 2 mmol) was added 1-t-butoxycarbonyl-3,3-dimethylthiourea (409 mg, 2 mmol) and HgCl2 (543 mg, 2 mmol). The mixture was stirred at room temperature for 1 h and then filtered on a pad of celite. The residue was washed with ethyl acetate, the organic layer washed several times with water, dried and evaporated to dryness. The residue was chromatographed on silica gel using as eluant ethyl acetate/cyclohexane 2:1. The above obtained BOC-derivative was taken up in trifluoroacetic acid (10 ml) and then stirred for 1 h at room temperature. Ethyl acetate was added, the organic layer washed with 1N sodium hydroxide and brine, dried and evaporated. The residue was chromatographed on a LoBar RP18 column with water as eluant to give pure title compound after freeze-drying. Yield 50% (268 mg).

후처리

  1. filtrationfiltered on a pad of celite
  2. washThe residue was washed with ethyl acetate
  3. washthe organic layer washed several times with water
  4. customdried
  5. customevaporated to dryness
  6. customThe residue was chromatographed on silica gel using as eluant ethyl acetate/cyclohexane 2:1
  7. customThe above obtained BOC-derivative
  8. stirringstirred for 1 h at room temperature
  9. washthe organic layer washed with 1N sodium hydroxide and brine
  10. customdried
  11. customevaporated
  12. customThe residue was chromatographed on a LoBar RP18 column with water as eluant

출처 및 근거

ORD 기록
ord-40844b03e22c4d1bbb85c3fbe6bee499
출처 데이터셋
uspto-grants-1999_05
특허 번호
US05905149

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