Reaktion #1128069

Reaktionsgleichung

2-(2,5-Dichloro-pyrimidin-4-ylamino)-3,N-dimethyl-benzamide

7-Amino-5,5-dimethyl-1,3,4,5-tetrahydro-benzo[b]azepin-2-one

DL-10-Camphorsulfonic acid

→

2-[5-Chloro-2-(5,5-dimethyl-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepin-7-ylamino)-pyrimidin-4-ylamino]-3,N-dimethyl-benzamide

Ausbeute 3.0%

Lösungsmittel

isopropanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeMicrowaved
2. 2
   Sonstigereaction at 120° C. for 20 minutes
3. 3
   SonstigeEvaporated off solvent
4. 4
   Sonstigepurified with normal phase chromatography

Vorschrift

Combined 2-(2,5-Dichloro-pyrimidin-4-ylamino)-3,N-dimethyl-benzamide (90 mg, 0.289 mmol), 7-Amino-5,5-dimethyl-1,3,4,5-tetrahydro-benzo[b]azepin-2-one (62 mg, 0.304 mmol), DL-10-Camphorsulfonic acid (84 mg, 0.362 mmol) and isopropanol (3 mL) in a microwave tube. Microwaved reaction at 120° C. for 20 minutes. Evaporated off solvent and purified with normal phase chromatography to yield an off-white solid, 2-[5-Chloro-2-(5,5-dimethyl-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepin-7-ylamino)-pyrimidin-4-ylamino]-3,N-dimethyl-benzamide (4.2 mg, 3%). LCMS: m/z=479.37 (M+H+), 1H NMR (400 MHz, CDCl3) δ 8.67 (s, 1H), 8.06 (d, 1H, J=1.3 Hz), 7.39 (m, 4H), 7.27 (m, 1H), 7.18 (s, 1H), 7.14 (s, 1H), 6.66 (d, 1H, J=8.6 Hz), 6.10 (m, 1H), 2.92 (m, 3H), 2.34 (m, 2H), 2.25 (s, 3H), 2.05 (m, 2H), 1.30 (s, 6H).

Quelle