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

HRID 389978
Notes
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Reaction equation

HRID 389978 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 845041-Hexanesulfonyl chlorideHCID 67419145[4-(6-Aminopyridin-3-YL)piperazin-1-YL]-(2-trifluoromethylphenyl)methanone

Product 1

HCID 11294961Hexane-1-sulfonic acid {5-[4-(2-trifluoromethylbenzoyl)piperazin-1-YL]pyridin-2-YL}amideYield 8%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolvent
HCID 8857
Ethyl Acetate
Solvent

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

  1. washwashed with brine
  2. dry with materialdried over anhydrous MgSO4
  3. concentrationconcentrated in vacuo
  4. customPurification by preparative thin layer chromatography

Sources & evidence

ORD record
ord-e33776045e6c44e9acbd26e6e6c5ac00
Source dataset
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08383628B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes