8-Amino-4-cyclopropylmethyl-7-methoxy-1,3,4,5-tetrahydro-benzo[e][1,4]diazepin-2-one → 8-{5-Chloro-4-[2-(pyrrolidine-1-sulfonyl)-phenylamino]-pyrimidin-2-ylamino}-4-cyclopropylmethyl-7-methoxy-1,3,4,5-tetrahydro-benzo[e][1,4]diazepin-2-one

Participants

Reaction Steps

In an analogous manner to procedure 1656g, 8-amino-4-cyclopropylmethyl-7-methoxy-1,3,4,5-tetrahydro-benzo[e][1,4]diazepin-2-one (125 mg, 0.48 mmol) and (2,5-dichloro-pyrimidin-4-yl)-[2-(pyrrolidine-1-sulfonyl)-phenyl]-amine (149 mg, 0.40 mmol) were coupled to afford 8-{5-chloro-4-[2-(pyrrolidine-1-sulfonyl)-phenylamino]-pyrimidin-2-ylamino}-4-cyclopropylmethyl-7-methoxy-1,3,4,5-tetrahydro-benzo[e][1,4]diazepin-2-one (30 mg, 10%) as a pale yellow solid following flash chromatography on silica gel (0-10% MeOH-EtOAc);); 1H NMR (400 MHz, CDCl3) δ 9.44 (s, 1H), 8.45 (d, J=8 Hz, 1H), 8.19 (s, 1H), 8.07 (s, 1H), 7.98 (d, J=8 Hz, 1H), 7.62 (m, 2H), 7.35 (m, 1H), 7.07 (s, 1H), 6.83 (s, 1H), 3.94 (s, 3H), 3.82 (s, 2H), 3.53 (s, 2H), 3.28 (t, J=6 Hz, 4H), 2.60 (d, J=6 Hz, 2H), 1.82 (t, J=6 Hz, 4H), 0.96 (m, 1H), 0.60 (m, 2H), 0.23 (m, 2H); MS (m/e) 599 (M+1); mp 142° C.

Provenance & Evidence