Dimethylformamide → 2-Methoxy-6-(6-methoxy-4-((1-phenyl-1H-1,2,3-triazol-4-yl)methoxy)benzofuran-2-yl)imidazo[2,1-b][1,3,4]thiadiazole

HRID 1424355

Reaktionsgleichung

Reaktionsgleichung von HRID 1424355
[CH3:1][O:2][C:3]1[S:7][C:6]2=[N:8][C:9]([C:11]3[O:12][C:13]4[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[C:16]([O:22][CH2:23][C:24]#[CH:25])[C:14]=4[CH:15]=3)=[CH:10][N:5]2[N:4]=1.[N:26]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[N+:27]=[N-:28].CN(C=O)C.O[C@H]([C@@H]1C([O-])=C(O)C(=O)O1)CO.[Na+]>ClCCl.O.O.O.O.O.S([O-])([O-])(=O)=O.[Cu+2]>[CH3:1][O:2][C:3]1[S:7][C:6]2=[N:8][C:9]([C:11]3[O:12][C:13]4[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[C:16]([O:22][CH2:23][C:24]5[N:28]=[N:27][N:26]([C:29]6[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=6)[CH:25]=5)[C:14]=4[CH:15]=3)=[CH:10][N:5]2[N:4]=1

Komponenten

7

Edukt 4

HCID 6228DimethylformamideHCID 69319AzidobenzeneHCID 23667548Sodium AscorbateHCID 867008962-Methoxy-6-(6-methoxy-4-(prop-2-yn-1-yloxy)benzofuran-2-yl)imidazo[2,1-b][1,3,4]thiadiazole

Produkt 1

HCID 721933332-Methoxy-6-(6-methoxy-4-((1-phenyl-1H-1,2,3-triazol-4-yl)methoxy)benzofuran-2-yl)imidazo[2,1-b][1,3,4]thiadiazoleAusbeute 49 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24463Copper sulfate pentahydrateKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of 2-methoxy-6-(6-methoxy-4-(prop-2-yn-1-yloxy)benzofuran-2-yl)imidazo[2,1-b][1,3,4]thiadiazole (Example 9A, 20 mgs, 0.056 mmol) and azidobenzene (Example 9B, 19 mgs, 0.159 mmol) in DMF (4 mL, 51.7 mmol) was treated at r.t. and under a nitrogen atmosphere with sodium (R)-2-((S)-1,2-dihydroxyethyl)-4-hydroxy-5-oxo-2,5-dihydrofuran-3-olate (8 mgs, 0.040 mmol) and copper(II) sulfate pentahydrate (5 mgs, 0.020 mmol). The mixture was stirred for 2 hours (reaction followed by HPLC) and was then diluted with dichloromethane (60 mL) and washed with sat. NaHCO3, brine and dried (MgSO4). The solvent was evaporated and the solid residue was triturated with acetonitrile (2×1 mL) and lyophilized to give the title material (13 mgs, 0.027 mmol, 49% yield). LC (Method A): 2.213 min. HRMS (ESI) calcd for C23H19N6O4S [M+H]+ m/z 475.1183. found 475.1204. 1H NMR (DMSO-d6, 400 MHz) δ ppm: 9.04 (s, 1H), 8.37 (s, 1H), 7.90-7.99 (m, 2H), 7.58-7.67 (m, 2H), 7.51 (tt, J=7.4, 1.2 Hz, 1H), 6.97-7.03 (m, 1H), 6.83-6.88 (m, 1H), 6.71 (d, J=1.6 Hz, 1H), 5.38 (s, 3H), 4.20 (s, 3H), 3.83 (s, 3H).

Aufarbeitung

  1. custom(reaction followed by HPLC)
  2. washwashed with sat. NaHCO3, brine
  3. dry with materialdried (MgSO4)
  4. customThe solvent was evaporated
  5. customthe solid residue was triturated with acetonitrile (2×1 mL)

Quellen und Nachweise

ORD-Eintrag
ord-562fb128c29d481b8b68457c56d3a0f8
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08927688B2

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