1-Hexanesulfonyl chloride → Hexane-1-sulfonic acid {5-[4-(2-trifluoromethylbenzoyl)piperazin-1-YL]pyridin-2-YL}amide

HRID 2357889Notes

Reaction equation

[NH2:1][C:2]1[N:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[C:22]([F:25])([F:24])[F:23])=[O:15])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[CH2:26]([S:32](Cl)(=[O:34])=[O:33])[CH2:27][CH2:28][CH2:29][CH2:30][CH3:31]>N1C=CC=CC=1.C(OCC)(=O)C>[F:23][C:22]([F:25])([F:24])[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[C:14]([N:11]1[CH2:10][CH2:9][N:8]([C:5]2[CH:4]=[CH:3][C:2]([NH:1][S:32]([CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])(=[O:34])=[O:33])=[N:7][CH:6]=2)[CH2:13][CH2:12]1)=[O:15]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of [4-(6-aminopyridin-3-yl)piperazin-1-yl]-(2-trifluoromethylphenyl)-methanone (0.035 g, 0.10 mmol) in pyridine (3 mL) was added hexanesulfonyl chloride (0.022 mL, 0.12 mmol). After heating at 60° C. for 20 h, the mixture was diluted with ethyl acetate (100 mL), washed with brine, dried over anhydrous MgSO4 and concentrated in vacuo. Purification by preparative thin layer chromatography afforded the title compound as a white solid (3.8 mg, 8% yield). 1H NMR (300 MHz, CDCl3) δ 7.66, 7.29, 4.08, 3.91, 3.38, 3.27, 3.08, 1.84, 1.35, 1.27, 0.87. MS (ES+) m/z 499.4 (M+1).

Workup

washwashed with brine
dry with materialdried over anhydrous MgSO4
concentrationconcentrated in vacuo
customPurification by preparative thin layer chromatography

Sources & evidence

ORD record: ord-798d48cd61174ddebb7f80fd49efad3f
Source dataset: uspto-grants-2010_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07763618B2

Reaction notes

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