Trifluoroacetic acid → 4-(5-Benzyl-2-(6-methoxypyridin-3-ylamino)pyridin-3-yl)-6-methyl-1,3,5-triazin-2-amine

HRID 1812019

Reaktionsgleichung

Reaktionsgleichung von HRID 1812019
[CH2:1]([C:8]1[CH:9]=[C:10]([C:23]2[N:28]=[C:27]([CH3:29])[N:26]=[C:25]([N:30](CC3C=CC(OC)=CC=3)CC3C=CC(OC)=CC=3)[N:24]=2)[C:11]([NH:14][C:15]2[CH:16]=[N:17][C:18]([O:21][CH3:22])=[CH:19][CH:20]=2)=[N:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O>FC(F)(F)S(O)(=O)=O>[CH2:1]([C:8]1[CH:9]=[C:10]([C:23]2[N:28]=[C:27]([CH3:29])[N:26]=[C:25]([NH2:30])[N:24]=2)[C:11]([NH:14][C:15]2[CH:16]=[N:17][C:18]([O:21][CH3:22])=[CH:19][CH:20]=2)=[N:12][CH:13]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 666119904-(5-benzyl-2-(6-methoxypyridin-3-ylamino)pyridin-3-yl)-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amine

Produkt 1

HCID 595484534-(5-Benzyl-2-(6-methoxypyridin-3-ylamino)pyridin-3-yl)-6-methyl-1,3,5-triazin-2-amineAusbeute 22,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 62406Trifluoromethanesulfonic acidKatalysator

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of 4-(5-benzyl-2-(6-methoxypyridin-3-ylamino)pyridin-3-yl)-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amine (110 mg, 0.172 mmol) in TFA (265 μL, 3.44 mmol) was treated with a couple of drops of trifluoromethanesulfonic acid (15.27 μL, 0.172 mmol) and the mixture was heated at 80° C. overnight. After cooling, the mixture was concentrated and the residue was dissolved in 5% MeOH/DCM and adsorbed onto a plug of silica gel and chromatographed through a Redi-Sep pre-packed silica gel column (pure DCM to 3% MeOH in DCM w/NH3) to give 4-(5-benzyl-2-(6-methoxypyridin-3-ylamino)pyridin-3-yl)-6-methyl-1,3,5-triazin-2-amine (15 mg, 0.038 mmol, 21.84% yield) as a yellow solid. 1H NMR (400 MHz, d6-DMSO) δ 11.68 (s, 1H); 8.61 (d, J=2.15 Hz, 1H); 8.53 (d, J=2.54 Hz, 1H); 8.23 (d, J=2.15 Hz, 1H); 8.16 (dd, J=8.80, 2.74 Hz, 1H); 7.83 (br. s., 1H); 7.69 (br. s., 1H); 7.11-7.45 (m, 5H); 6.81 (d, J=8.80 Hz, 1H); 3.94 (s, 2H); 3.84 (s, 3H). m/z (ESI, +ve ion) 400.0 (M+H)+.

Aufarbeitung

  1. temperatureAfter cooling
  2. concentrationthe mixture was concentrated
  3. dissolutionthe residue was dissolved in 5% MeOH/DCM
  4. customchromatographed through a Redi-Sep pre-packed silica gel column (pure DCM to 3% MeOH in DCM w/NH3)

Quellen und Nachweise

ORD-Eintrag
ord-e105dd2a4ce84351930890b4d0c89a57
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08362241B2

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