Water → HCID 86690646, compound

HRID 1505613Notes

Reaction equation

HRID 1505613 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10]2[CH:15]=[CH:14][C:13]([CH2:16][NH:17][S:18]([CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)(=[O:20])=[O:19])=[CH:12][CH:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[H-].[Na+].FC(F)(F)S(O[CH2:36][C:37]([F:40])([F:39])[F:38])(=O)=O.O>CN(C)C(=O)C>[C:1]([N:4]1[CH2:5][CH2:6][N:7]([C:10]2[CH:11]=[CH:12][C:13]([CH2:16][N:17]([CH2:36][C:37]([F:40])([F:39])[F:38])[S:18]([CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)(=[O:20])=[O:19])=[CH:14][CH:15]=2)[CH2:8][CH2:9]1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 803662,2,2-Trifluoroethyl trifluoromethanesulfonateHCID 86690645HCID 86690645, compound

Product 1

HCID 86690646HCID 86690646, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

To a solution of N-[[4-(4-acetylpiperazin-1-yl)phenyl]methyl]-1-phenyl-methanesulfonamide (100 mg, 0.25 mmol) in N,N-dimethylacetamide (3 mL) was added sodium hydride (60% in mineral oil) (11.3 mg, 0.28 mmol) and stirred at ambient temperature for 30 minutes. 2,2,2-Trifluoroethyl trifluoromethanesulfonate (72 mg, 0.31 mmol) was then added and stirred at ambient temperature for 16 hours. Water was added and the reaction was partitioned between water and dichloromethane. The dichloromethane layer was isolated with a phase separator cartridge and concentrated and purified by preparative reverse phase HPLC to yield 47 mg of N-(4-(4-acetylpiperazin-1-yl)benzyl)-1-phenyl-N-(2,2,2-trifluoroethyl)methanesulfonamide. 1H NMR (400 MHz, DMSO) δ 7.47-7.32 (m, 5H), 7.21 (d, J=8.5 Hz, 2H), 6.95 (d, J=8.5 Hz, 2H), 4.52 (s, 2H), 4.27 (s, 2H), 3.83 (q, J=9.3 Hz, 2H), 3.62-3.51 (m, 4H), 3.22-3.13 (m, 2H), 3.13-3.03 (m, 2H), 2.03 (s, 3H); LCMS (m/z) ES+ 470.1 [M+1]+.

Workup

  1. stirringstirred at ambient temperature for 16 hours
  2. customthe reaction was partitioned between water and dichloromethane
  3. customThe dichloromethane layer was isolated with a phase separator cartridge
  4. concentrationconcentrated
  5. custompurified by preparative reverse phase HPLC

Sources & evidence

ORD record
ord-39cab4208baa40e38c2df765726b28fb
Source dataset
uspto-grants-2015_12
Patent number
US09216988B2

Reaction notes

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