Diisopropylethylamine → N-(1-{2-[3-(2-Methyl-quinolin-4-yl)-ureido]-ethyl}-piperidin-4-yl)-4-trifluoromethyl-benzenesulfonamide

HRID 2223692Notes

Reaction equation

[F:1][C:2]([F:14])([F:13])[C:3]1[CH:8]=[CH:7][C:6]([S:9](Cl)(=[O:11])=[O:10])=[CH:5][CH:4]=1.[NH2:15][CH:16]1[CH2:21][CH2:20][N:19]([CH2:22][CH2:23][NH:24][C:25]([NH:27][C:28]2[C:37]3[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=3)[N:31]=[C:30]([CH3:38])[CH:29]=2)=[O:26])[CH2:18][CH2:17]1.CCN(C(C)C)C(C)C>C1COCC1>[CH3:38][C:30]1[CH:29]=[C:28]([NH:27][C:25](=[O:26])[NH:24][CH2:23][CH2:22][N:19]2[CH2:20][CH2:21][CH:16]([NH:15][S:9]([C:6]3[CH:7]=[CH:8][C:3]([C:2]([F:14])([F:13])[F:1])=[CH:4][CH:5]=3)(=[O:11])=[O:10])[CH2:17][CH2:18]2)[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[N:31]=1

Participants

Conditions

Temperature: 40 °C

Procedure

A solution of 4-trifluoromethyl-benzenesulfonyl chloride (0.03 mmol) in THF (1 mL) is added to a mixture of 1-[2-(4-amino-piperidin-1-yl)-ethyl]-3-(2-methyl-quinolin-4-yl)-urea (0.025 mmol), DIPEA (6 μL) and THF (1 mL). The reaction mixture is heated at 40° C. for 18 h, and then is evaporated to dryness. The residue is taken up in formic acid (1 mL), and purified by preparative HPLC to provide the title compound.

Workup

customis evaporated to dryness
custompurified by preparative HPLC

Sources & evidence

ORD record: ord-92cd7b79463f42909f541a73e658acb5
Source dataset: uspto-grants-2008_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07375227B2

Reaction notes

Loading…