p-Toluenesulfonic acid → 4-[(4-Bromo-3-hydroxybenzyl)(4-cyanophenyl)amino]-4H-[1,2,4]triazole

HRID 1685661

Reaktionsgleichung

Reaktionsgleichung von HRID 1685661
O1CCCCC1[O:7][C:8]1[CH:9]=[C:10]([CH:26]=[CH:27][C:28]=1[Br:29])[CH2:11][N:12]([C:18]1[CH:23]=[CH:22][C:21]([C:24]#[N:25])=[CH:20][CH:19]=1)[N:13]1[CH:17]=[N:16][N:15]=[CH:14]1.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[Br:29][C:28]1[CH:27]=[CH:26][C:10]([CH2:11][N:12]([C:18]2[CH:23]=[CH:22][C:21]([C:24]#[N:25])=[CH:20][CH:19]=2)[N:13]2[CH:14]=[N:15][N:16]=[CH:17]2)=[CH:9][C:8]=1[OH:7]

Komponenten

4

Edukt 2

HCID 6101p-Toluenesulfonic acidHCID 167493314-[(3-(tetrahydropyran-2-yloxy)-4-bromobenzyl)(4-cyanophenyl)amino]-4H-[1,2,4]triazole

Produkt 1

HCID 167493324-[(4-Bromo-3-hydroxybenzyl)(4-cyanophenyl)amino]-4H-[1,2,4]triazole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

The title compound was prepared by adapting the method reported by Tafi et al.[Tafi,2002] with the following modifications. To a solution of 4-[(3-(tetrahydropyran-2-yloxy)-4-bromobenzyl)(4-cyanophenyl)amino]-4H-[1,2,4]triazole (3.05 g, 6.71 mmol) in MeOH (60 mL) was added a catalytic amount of p-toluenesulfonic acid at 0° C. and the mixture was stirred (allowing to slowly warm to room temperature) overnight. The solvent was removed in vacuo and the residue dissolved in EtOAc (100 mL). The organic fraction was washed with Na2CO3 solution (1M aqueous solution, 3×50 mL), brine (3×50 mL) and dried (Na2SO4). The solvent was removed in vacuo and the pale yellow residue recrystallised from EtOH to give STX1216 as an off-white powder (1.48 g, 60%); δH (400 MHz, DMSO-d6) 5.00 (s, 2H), 6.72 (dd, J=8.3, 2.1, 1H), 6.76 (AA′BB′, 2H), 6.86 (d, J=1.8, 1H), 7.43 (d, J=8.0, 1H), 7.78 (AA′BB′, 2H), 8.81 (s, 2H), 10.32 (s, 1H—exchanges with D2O); δC (100 MHz, DMSO-d6) 57.08 (CH2), 103.32, 109.42 114.07 (2×CH), 116.66 (CH), 119.51 (CH), 120.90 (CH), 133.54 (2×CH), 134.45 (2×CH), 136.14, 143.90, 151.82, 154.60; LRMS (FAB+) m/z (rel. intensity) 372.1 (94, [C16H12N5O81Br+H], 370.1 (100, [C16H12N5O79Br+H]); LC-MS (ES−) TR=1.98 min, m/z 368.1 (C16H12N5O79Br—H), 370.1 (C16H12N5O81Br—H); HPLC tR=1.77 min (100%); HRMS (FAB+) Found 372.02789; C16H13N5O81Br requires 372.02830. Found: C, 51.6; H, 3.4; N, 18.9; C16H12N5OBr requires C, 51.9; H, 3.3; N, 18.9%.

Aufarbeitung

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue dissolved in EtOAc (100 mL)
  3. washThe organic fraction was washed with Na2CO3 solution (1M aqueous solution, 3×50 mL), brine (3×50 mL)
  4. dry with materialdried (Na2SO4)
  5. customThe solvent was removed in vacuo
  6. customthe pale yellow residue recrystallised from EtOH

Quellen und Nachweise

ORD-Eintrag
ord-0d75467a714847edb00556db6b700ca2
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08148415B2

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