Diisopropylethylamine → 8-Methyl-7-{[4-({4-[(trifluoromethyl)oxy]phenyl}sulfonyl)-1-piperazinyl]carbonyl}quinoline

To the solution of 8-methyl-7-quinolinecarboxylic acid (may be prepared as described in Intermediate 2; 90 mg, 0.483 mmol) in N,N-Dimethylformamide (DMF) (2 ml), HATU (193 mg, 0.508 mmol) was added at room temperature. The reaction was stirred for 20 min and then 1-({4-[(trifluoromethyl)oxy]phenyl}sulfonyl)piperazine (may be prepared as described in Intermediate 11; 150 mg, 0.483 mmol) was added followed by DIPEA (0.211 ml, 1.209 mmol) and the reaction mixture was stirred for 3 hours. The reaction mixture was poured into the separating funnel and partitioned between ethyl acetate (25 ml) and sodium hydroxide (15 ml). The organic phase was washed with sodium hydroxide (2×10 ml), water (2×10 ml) and brine (10 mL) before it was dried using phase separator and the solvent was removed under vacuum. The crude product was purified by MDAP to give the title compound as a white solid (115 mg).

1. stirringthe reaction mixture was stirred for 3 hours
2. additionThe reaction mixture was poured into the separating funnel
3. custompartitioned between ethyl acetate (25 ml) and sodium hydroxide (15 ml)
4. washThe organic phase was washed with sodium hydroxide (2×10 ml), water (2×10 ml) and brine (10 mL) before it
5. customwas dried
6. customthe solvent was removed under vacuum
7. customThe crude product was purified by MDAP

ORD record

ord-abdbf5896023457fa2d80a1e3c818abb

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08697703B2