7-Chloro-3-(2,2,2-trifluoroacetyl)-6-trifluoromethylsulfonyloxy-2,3,4,5-tetrahydro-1H-benzo[d]azepine → 7-chloro-6-{4-[2-(3-methyl-butylamino)-thiazol-4-yl]-benzylamino}-3-(2,2,2-trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine

Participants

Reaction Steps

Use a method similar to the General Procedure 1-2 to couple 7-chloro-3-(2,2,2-trifluoroacetyl)-6-trifluoromethanesulfonyloxy-2,3,4,5-tetrahydro-1H-benzo[d]azepine (380 mg, 0.89 mmol) with 4-[2-(3-methyl-butylamino)-thiazol-4-yl]-benzylamine (443 mg, 1.6 mmol) in toluene (12 mL). Purify the crude mixture by chromatography on silica gel (25 g) eluting with hexane/(EtOAc with 1% methanol) (20:1 to 7:3 gradient) to obtain 7-chloro-6-{4-[2-(3-methyl-butylamino)-thiazol-4-yl]-benzylamino}-3-(2,2,2-trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine (368 mg, 75%). MS (ES+) m/z: 551.4 (M+H)+.

Provenance & Evidence