4-[(3-benzyloxybenzyl)(4-cyanophenyl)amino]-4H-[1,2,4]triazole → 4-[(3-Hydroxybenzyl)(4-cyanophenyl)amino]-4H-[1,2,4]triazole

HRID 1685645

Reaktionsgleichung

Reaktionsgleichung von HRID 1685645
C([O:8][C:9]1[CH:10]=[C:11]([CH:27]=[CH:28][CH:29]=1)[CH2:12][N:13]([C:19]1[CH:24]=[CH:23][C:22]([C:25]#[N:26])=[CH:21][CH:20]=1)[N:14]1[CH:18]=[N:17][N:16]=[CH:15]1)C1C=CC=CC=1>C1COCC1.CO.[Pd]>[OH:8][C:9]1[CH:10]=[C:11]([CH:27]=[CH:28][CH:29]=1)[CH2:12][N:13]([C:19]1[CH:24]=[CH:23][C:22]([C:25]#[N:26])=[CH:21][CH:20]=1)[N:14]1[CH:15]=[N:16][N:17]=[CH:18]1

Komponenten

4

Edukt 1

HCID 219768914-[(3-benzyloxybenzyl)(4-cyanophenyl)amino]-4H-[1,2,4]triazole

Produkt 1

HCID 219768414-[(3-Hydroxybenzyl)(4-cyanophenyl)amino]-4H-[1,2,4]triazoleAusbeute 88,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 21899815MeOH tetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 4-[(3-Benzyloxybenzyl)(4-cyanophenyl)amino]-4H-[1,2,4]triazole (0.4 g, 1.05 mmol) in anhydrous THF/MeOH (20 mL) was added Pd—C (10% by wt., 0.04 g). The black suspension was then stirred under an atmosphere of hydrogen (balloon) for 16 h. The catalyst was removed by filteration through Celite® and exhaustively washed with THF. The filtrate was concentrated in vacuo to give a beige residue. Recrystallisation from EtOH gave STX333 as a colourless solid (0.27 g, 88%) after recrystallisation; δH (400 MHz, DMSO-d6) 4.97 (s, 2H), 6.68 (AA′BB′, 2H), 6.72-6.75 (m, 3H), 7.11 (m, 1H), 7.76 (AA′BB′, 2H), 8.77 (s, 2H), 9.49 (br s, 1H—exchanges with D2O); LRMS (FAB+) m/z (rel. intensity) 292 (100%, [M+H]), 223 (42, [M+H-triazole]); HPLC tR=2.22 min, (96%); HRMS (FAB+) Found 292.1198; C16H13N5O requires 292.1192;

Aufarbeitung

  1. customThe catalyst was removed by filteration through Celite®
  2. washexhaustively washed with THF
  3. concentrationThe filtrate was concentrated in vacuo
  4. customto give a beige residue
  5. customRecrystallisation from EtOH

Quellen und Nachweise

ORD-Eintrag
ord-e49ea1753fc0401984bc7296630034d3
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08148415B2

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