1,4-Dibromobutane → HCID 68033148, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of N-(2-aminoethylsulfonyl)-4-(4-(1-(4-chlorophenyl)cyclopropylamino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-ylamino)benzamide HCl salt (20 mg, 0.031 mmol) in Acetonitrile (Volume: 2 mL) was added 1,4-dibromobutane (6.96 mg, 0.032 mmol) and POTASSIUM CARBONATE (21.23 mg, 0.154 mmol). The mixture was heated to 65° C. for 16 h. After cooling to rt, the mixture was diluted with EtOAc, washed with water, and brine. The organic layer was dried over MgSO4 and concentrated. The crude product was purified by rev. phase preparative HPLC (Column: Sunfire prep C18 OBO 5 uM, 30×100 mm by Waters Corp) using a gradient of 20-100% ACN/water w/0.1% TFA modifier to give 4-(4-(1-(4-chlorophenyl)cyclopropylamino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-ylamino)-N-(2-(pyrrolidin-1-yl)ethylsulfonyl)benzamide (3 mg) as the TFA salt. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.17-1.48 (m, 4H), 1.80-2.12 (m, 4H), 3.37-4.41 (m, 8H), 5.00 (q, J=9.0 Hz, 2H), 7.15-7.44 (m, 4H), 7.67-7.86 (m, 3H), 7.93 (s, 1H), 8.86 (br. s., 1H), 9.71 (br. s., 1H), 10.13 (br. s., 1H); LC-MS (Condition A), MS m/z (M++H) 640.0.

Provenance & Evidence