Water → HCID 178479963, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 2,4,5-trichloropyrimidine (550.5 mg, 3.001 mmol) and 7-amino-4-(trans-4-hydroxycyclohexyl)-2-methyl-2,3-dihydro-1H-isoindol-1-one (166.6 mg, 0.6400 mmol) in DMA (8 mL) was charged with DIPEA (1 mL, 6 mmol) and then heated to 100° C. overnight. The reaction mixture was cooled to ambient temperature, diluted with EtOAc, and poured into water. The material was extracted thrice with EtOAc and the combined organic layers were washed with brine, dried over anhydrous Na2SO4, filtered, and concentrated in vacuo. The crude material was adsorbed onto a pre-filled solid loading cartridge [RediSepRf 25 gram] and purified using the Teledyne/ISCO system [RediSepRf 12 gram silica], eluting first with 0-100% EtOAc:CH2Cl2 and then 0-5% MeOH:CH2Cl2. The desired fractions were pooled together and concentrated in vacuo, giving the title material as a brown solid, 173.0 mg. 1H NMR (400 MHz, DMSO-d6) δ ppm 11.07 (s, 1H), 8.52 (s, 1H), 8.43 (d, J=8.6 Hz, 1H), 7.52 (d, J=8.6 Hz, 1H), 4.60 (d, J=4.5 Hz, 1H), 4.57 (s, 2H), 3.48 (ddd, J=15.0, 6.4, 4.4 Hz, 1H), 3.10 (s, 3H), 1.93 (br s, 2H), 1.77 (br d, J=12.4 Hz, 2H), 1.55 (dtd, J=13.0, 12.7, 2.5 Hz, 2H), 1.22-1.37 (m, 3H). MS (ES+): m/z 407.10/409.10 (100/72) [MH+]. HPLC: tR=1.40 min (TOF, polar—3 min).

Provenance & Evidence