Dibenzyl ether → HCID 178484195, Verbindung

HRID 424903Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 424903
[CH2:1](OCC1C=CC=CC=1)C1C=CC=CC=1.[NH2:16][CH2:17][CH2:18][N:19]1[C:27]2[C:22](=[CH:23][C:24]([N:28]3[C:32]([C:33]4[CH:38]=[C:37]([CH:39]([CH3:41])[CH3:40])[C:36]([O:42]CC5C=CC=CC=5)=[CH:35][C:34]=4[O:50]CC4C=CC=CC=4)=[N:31][N:30]=[C:29]3[OH:58])=[CH:25][CH:26]=2)[CH:21]=[CH:20]1>>[OH:58][C:29]1[N:28]([C:24]2[CH:23]=[C:22]3[C:27](=[CH:26][CH:25]=2)[N:19]([CH2:18][CH2:17][NH:16][CH3:1])[CH:20]=[CH:21]3)[C:32]([C:33]2[CH:38]=[C:37]([CH:39]([CH3:40])[CH3:41])[C:36]([OH:42])=[CH:35][C:34]=2[OH:50])=[N:31][N:30]=1

Komponenten

3

Edukt 2

HCID 7657Dibenzyl etherHCID 178438831HCID 178438831, Verbindung

Produkt 1

HCID 178484195HCID 178484195, Verbindung

Versuchsvorschrift

The benzylether [4-(1-(2-aminoethyl)-1H-indol-5-yl)-5-(2,4-bis(benzyloxy)-5-isopropylphenyl)-4H-1,2,4-triazol-3-ol; 188 mg, 0.33 mmol) was dissolved in 6 ml degassed THF/methanol (1:1). 50 mg Pd/C (10%) was added and the mixture stirred under hydrogen (balloon) at rt for 5 h. After filtration the solvent was removed and the crude purified by chromatography on silica with DCM/MeOH (5-20%)/NH4OH (0.5%) to yield 71 mg (0.18 mmol) 4-(5-hydroxy-4-(1-(2-(methylamino)ethyl)-1H-indol-5-yl)-4H-1,2,4-triazol-3-yl)-6-isopropylbenzene-1,3-diol. This amine (50 mg, 0.125) was added to 4-(2,5-dioxopyrrolidin-1-yl)butanoic acid (26 mg, 0.14 mmol), EDC (38 mg, 0.2 mmol) and HOBt (27 mg, 0.2 mmol) in 1.5 ml DMF at rt. The mixture was stirred for 12 h and then ethyl acetate and water added. The aq. Phase was extracted twice with ethyl acetate and the combined organic extracts washed with brine and dried over MgSO4. The crude was purified by chromatography on silica with DCM/MeOH (3-10%) to yield 34 mg (0.061 mmol) product.

Aufarbeitung

  1. dissolution188 mg, 0.33 mmol) was dissolved in 6 ml
  2. customdegassed THF/methanol (1:1)
  3. addition50 mg Pd/C (10%) was added
  4. filtrationAfter filtration the solvent
  5. customwas removed
  6. customthe crude purified by chromatography on silica with DCM/MeOH (5-20%)/NH4OH (0.5%)

Quellen und Nachweise

ORD-Eintrag
ord-7bc0e1383ee2413895c2a09e65442f0f
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08106083B2

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