4-(2-(2,2-Difluorobenzo[D][1,3]dioxol-5-ylamino)pyridin-3-YL)-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amine → 4-(2-(2,2-Difluorobenzo[d][1,3]dioxol-5-ylamino)pyridin-3-yl)-6-methyl-1,3,5-triazin-2-amine

HRID 1812037Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1812037
[F:1][C:2]1([F:44])[O:6][C:5]2[CH:7]=[CH:8][C:9]([NH:11][C:12]3[C:17]([C:18]4[N:23]=[C:22]([CH3:24])[N:21]=[C:20]([N:25](CC5C=CC(OC)=CC=5)CC5C=CC(OC)=CC=5)[N:19]=4)=[CH:16][CH:15]=[CH:14][N:13]=3)=[CH:10][C:4]=2[O:3]1>C(O)(C(F)(F)F)=O>[F:44][C:2]1([F:1])[O:6][C:5]2[CH:7]=[CH:8][C:9]([NH:11][C:12]3[C:17]([C:18]4[N:23]=[C:22]([CH3:24])[N:21]=[C:20]([NH2:25])[N:19]=4)=[CH:16][CH:15]=[CH:14][N:13]=3)=[CH:10][C:4]=2[O:3]1

Komponenten

3

Edukt 1

HCID 666109184-(2-(2,2-Difluorobenzo[D][1,3]dioxol-5-ylamino)pyridin-3-YL)-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amine

Produkt 1

HCID 595483914-(2-(2,2-Difluorobenzo[d][1,3]dioxol-5-ylamino)pyridin-3-yl)-6-methyl-1,3,5-triazin-2-amineAusbeute 3,83 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6422Trifluoroacetic acidLösungsmittel

Versuchsvorschrift

A solution of 4-(2-(2,2-difluorobenzo[d][1,3]dioxol-5-ylamino)pyridin-3-yl)-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amine (0.1352 g, 0.226 mmol) in TFA (8.0 mL) (Aldrich) was heated at 80° C. overnight. The solution was cooled to room temperature and the TFA was removed in vacuo. The residue was treated with a saturated solution of NaHCO3, the aqueous layer was extracted with DCM (3×15 mL), the layers were separated, the combined organic layers were dried and concentrated. The crude brown oil was dissolved in 2.5 mL of DMSO and purified by reversed phase chromatography (Gilson, 10-90% CH3CN in water with NH4OH additive: 0.1% v/v in each solvent). The fractions were concentrated in a Genevac Series II System to give 4-(2-(2,2-difluorobenzo[d][1,3]dioxol-5-ylamino)pyridin-3-yl)-6-methyl-1,3,5-triazin-2-amine (3.1 mg, 8.65 μmol, 3.83% yield) as a yellow amorphous solid. 1H NMR (400 MHz, d6-DMSO) δ 12.11 (s, 1H); 8.80 (dd, J=7.8, 2.0 Hz, 1H); 8.37 (dd, J=4.6, 2.1 Hz, 1H); 8.15 (d, J=2.2 Hz, 1H); 7.87 (br. s., 1H); 7.77 (br. s., 1H); 7.55 (dd, J=8.8, 2.2 Hz, 1H); 7.35 (d, J=8.8 Hz, 1H); 6.95 (dd, J=7.9, 4.6 Hz, 1H); 2.44 (s, 3H). m/z (ESI, +ve ion) 359.0 (M+H)+.

Aufarbeitung

  1. customthe TFA was removed in vacuo
  2. additionThe residue was treated with a saturated solution of NaHCO3
  3. extractionthe aqueous layer was extracted with DCM (3×15 mL)
  4. customthe layers were separated
  5. customthe combined organic layers were dried
  6. concentrationconcentrated
  7. dissolutionThe crude brown oil was dissolved in 2.5 mL of DMSO
  8. custompurified by reversed phase chromatography (Gilson, 10-90% CH3CN in water with NH4OH additive
  9. concentrationThe fractions were concentrated in a Genevac Series II System

Quellen und Nachweise

ORD-Eintrag
ord-c3756a827b7c48e69aaa7bdcd4313509
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08362241B2

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