Water → 1-[(3-Methyl-2-pyridinyl)carbonyl]-4-{[4-(trifluoromethyl)phenyl]sulfonyl}piperazine

To a solution of 1-{[4-(trifluoromethyl)phenyl]sulfonyl}piperazine (Description 1) (100 mg, 0.340 mmol) in DMF (5 ml) was added HOBT.H2O (52.0 mg, 0.340 mmol), HBTU (129 mg, 0.340 mmol), 3-methyl-2-pyridinecarboxylic acid (46.6 mg, 0.340 mmol) and DIPEA (0.178 ml, 1.019 mmol). The reaction mixture was stirred for 2 hours at room temperature. Reaction mixture was transferred to a 100 ml round bottom flask and was reduced to dryness in vacuo. The residue was dissolved in DCM (50 ml) and transferred to a separating funnel then was washed with saturated aq. NaHCO3 solution (5 ml), twice. The organic layer was collected and dried with dried magnesium sulphate. The solid was removed by filtration and the filtrate collected in a 250 ml round bottom flask and reduced to dryness in vacuo. The residue was then dissolved in 1.8 ml 1:1 MeCN/DMSO and purified by MDAP in 2 batches. The fractions containing desired product were combined in a 250 ml round bottom flask and reduced in vacuo to yield the title compound (91 mg).

1. customReaction mixture
2. customwas transferred to a 100 ml round bottom flask
3. customtransferred to a separating funnel
4. washthen was washed with saturated aq. NaHCO3 solution (5 ml)
5. customThe organic layer was collected
6. dry with materialdried with dried magnesium sulphate
7. customThe solid was removed by filtration
8. customthe filtrate collected in a 250 ml round bottom flask
9. dissolutionThe residue was then dissolved in 1.8 ml 1:1 MeCN/DMSO
10. custompurified by MDAP in 2 batches
11. additionThe fractions containing desired product
12. customwere combined in a 250 ml round bottom flask

ORD record

ord-a0dae1b96ba14871af6017fb09c888d8

Source dataset

uspto-grants-2013_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08530478B2