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

HRID 1064003Notes

Reaction equation

HRID 1064003 reaction equation
[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

Participants

5

Reactant 4

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

Product 1

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

Procedure

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 0-5.0% 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.

Workup

  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 0-5.0% methanol in DCM

Sources & evidence

ORD record
ord-05506dd271e14b56bef55778e2633097
Source dataset
uspto-grants-2005_11
Patent number
US06967216B2

Reaction notes

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