Reaktion #1128072

Reaktionsgleichung

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

8-Amino-2,3,4,5-tetrahydro-benzo[c]azepin-1-one

DL-10-Camphorsulfonic acid

→

2-[5-Chloro-2-(1-oxo-2,3,4,5-tetrahydro-1H-benzo[c]azepin-8-ylamino)-pyrimidin-4-ylamino]-3,N-dimethyl-benzamide

Ausbeute 17.3%

Lösungsmittel

isopropanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeMicrowaved
2. 2
   Sonstigereaction at 120° C. for 30 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 (100 mg, 0.321 mmol), 8-Amino-2,3,4,5-tetrahydro-benzo[c]azepin-1-one (69 mg, 0.392 mmol), DL-10-Camphorsulfonic acid (93 mg, 0.400 mmol) and isopropanol (4 mL) in a microwave tube. Microwaved reaction at 120° C. for 30 minutes. Evaporated off solvent and purified with normal phase chromatography to yield an off-white solid, 2-[5-Chloro-2-(1-oxo-2,3,4,5-tetrahydro-1H-benzo[c]azepin-8-ylamino)-pyrimidin-4-ylamino]-3,N-dimethyl-benzamide (25 mg, 17%). mp 259° C.; LCMS: m/z=451.36 (M+H+), 1H NMR (400 MHz, CD3OD) δ 8.02 (s, 1H), 7.69 (m, 1H), 7.58 (s, 1H), 7.42 (m, 2H), 7.37 (m, 1H), 7.30 (m, 1H), 6.97 (d, 1H, J=8.3 Hz), 4.24 (m, 1H), 3.50 (m, 1H), 3.15 (m, 1H), 3.02 (m, 2H), 2.82 (s, 3H), 2.73 (m, 2H), 2.24 (s, 3H), 1.97 (m, 2H).

Quelle