Dimethylformamide → 5,5-Dioxo-2-(pyrid-4-ylethylcarbonylamino)dibenzothiophene

HRID 2055311노트

반응식

HRID 2055311 반응식
[O:1]=[S:2]1(=[O:16])[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[C:4]2[CH:11]=[C:12]([NH2:15])[CH:13]=[CH:14][C:3]1=2.[N+](C1C=CC(COC([NH:28][C:29]2C=[CH:40][C:32]3SC4C=C[CH:37]=[CH:36][C:35]=4[C:31]=3[CH:30]=2)=O)=CC=1)([O-])=O.CCN=C=NCCCN(C)C.CN(C=[O:59])C>>[O:1]=[S:2]1(=[O:16])[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[C:4]2[CH:11]=[C:12]([NH:15][C:37]([CH2:36][CH2:35][C:31]3[CH:30]=[CH:29][N:28]=[CH:40][CH:32]=3)=[O:59])[CH:13]=[CH:14][C:3]1=2

참가 물질

5

반응물 4

HCID 6228DimethylformamideHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 149185295,5-Dioxo-2-aminodibenzothiopheneHCID 693158012-(4-Nitrobenzoxycarbonylamino)dibenzothiophene

생성물 1

HCID 693151165,5-Dioxo-2-(pyrid-4-ylethylcarbonylamino)dibenzothiophene

실험 절차

5,5-Dioxo-2-aminodibenzothiophene (J Med Chem, (1994), 37 (13), 2085-9; 115 mg, 0.5 mmol) was dissolved in DMF (2.0 ml) and 3-(pyridin-4-yl)propionic acid (Method 1; 75 mg, 0.5 mmol) was added in one portion followed by EDAC (115 mg, 0.5 mmol) and the resultant mixture was stirred for 72 hours at ambient temperature. It was then poured onto water (50 ml) and extracted with DCM (2×50 ml), dried and evaporated in vacuo. The residue thus obtained was purified by chromatography (Bond Elut column) eluted with 0-0.5% methanol in DCM to give the product as a colourless solid (31.8 mg). NMR 10.52 (brs, 1H), 8.46 (d, 2H), 8.32 (d, 1H), 7.97 (d, 1H), 7.94 (d, 1H), 7.88 (d, 1H), 7.76 (d, 1H), 7.70 (t, 1H), 7.64 (t, 1H), 7.26 (d, 2H), 2.93 (t, 2H), 2.75 (t, 2H); m/z 365.

후처리

  1. additionIt was then poured onto water (50 ml)
  2. extractionextracted with DCM (2×50 ml)
  3. customdried
  4. customevaporated in vacuo
  5. customThe residue thus obtained
  6. customwas purified by chromatography (Bond Elut column)
  7. washeluted with 0-0.5% methanol in DCM

출처 및 근거

ORD 기록
ord-51372d515d604c968b1690827b9500db
출처 데이터셋
uspto-grants-2008_02
특허 번호
US07332492B2

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