Diisopropylethylamine → HCID 67324636, compound

Participants

Reaction Steps

7-Quinolinecarboxylic acid (112 mg, 0.649 mmol) was weighed into a vial with the HATU (247 mg, 0.649 mmol), suspended in N,N-dimethylformamide (DMF) (2 ml) and treated with N,N-diisoproylethylamine (0.170 ml, 0.973 mmol). This mixture was stirred about 15 mins at ambient temperature. (3S)-3-methyl-1-{[4-(trifluoromethyl)phenyl]sulfonyl}piperazine (may be prepared in a similar manner as described in Intermediate 14; 100 mg, 0.324 mmol) was then added and stirring was continued. Stirring was stopped and the reaction mixture was left to stand overnight. The mixture was partitioned between DCM and sat aq. NaHCO3 solution (10 ml each). The layers were separated (hydrophobic frit) and the aqueous was washed with further DCM (2×5 ml). The combined organic layers were concentrated to leave an orange gum (still contained DMF). This was diluted with a mixture of MeCN and DMSO to give ˜1.8 ml orange solution which was purified by MDAP as two injections. The product fractions from the two runs were combined and concentrated to give the title compound as a colourless solid (119 mg).

Provenance & Evidence