Tetrahydrofuran → HCID 178521456, compound

HRID 1047363Notes

Reaction equation

HRID 1047363 reaction equation
Cl[CH2:2][C:3]([N:5]1[CH2:10][CH2:9][N:8]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=2)[CH2:7][CH2:6]1)=[O:4].[N+:21]([C:24]1[CH:29]=[CH:28][C:27]([NH:30][C@H:31]2[CH2:36][CH2:35][C@H:34]([OH:37])[CH2:33][CH2:32]2)=[CH:26][C:25]=1[C:38]([F:41])([F:40])[F:39])([O-:23])=[O:22].[H-].[Na+].O1CCCC1>ClCCl.CN(C)C=O>[N+:21]([C:24]1[CH:29]=[CH:28][C:27]([NH:30][C@H:31]2[CH2:36][CH2:35][C@H:34]([O:37][CH2:2][C:3]([N:5]3[CH2:10][CH2:9][N:8]([C:11]4[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=4)[CH2:7][CH2:6]3)=[O:4])[CH2:33][CH2:32]2)=[CH:26][C:25]=1[C:38]([F:39])([F:40])[F:41])([O-:23])=[O:22]

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 581182122-Chloro-1-[4-[4-(trifluoromethyl)phenyl]piperazin-1-yl]ethan-1-oneHCID 178526690HCID 178526690, compound

Product 1

HCID 178521456HCID 178521456, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

2-Chloro-1-[4-(4-trifluoromethyl-phenyl)-piperazin-1-yl]-ethanone (26 mg, 0.09 mmol, prepared in accordance with Example 4), trans-4-(4-nitro-3-trifluoromethyl-phenylamino)-cyclohexanol (26 mg, 0.09 mmol, prepare in accordance with Example 5), and sodium hydride (10 mg, 60% in oil, 0.26 mmol) were placed under an inert atmosphere. Tetrahydrofuran (1 mL) was added under stirring. Next, dimethylformamide (300 μL) was added under stirring. The resulting mixture was stirred for 40 min at room temperature and then diluted with dichloromethane (5 mL). The mixture was washed with water (5 mL) and then washed with saturated aqueous sodium hydrogencarbonate (5 mL). The organic phase was collected, dried over magnesium sulfate, filtered, and concentrated under vacuum. The crude product was purified by preparative HPLC. Following lyophilization of the fractions of interest, the desired product was isolated as a yellow solid (21 mg, 43% yield). The structure was confirmed using Protocol II-A. Calculated mass=575; observed mass=575; HPLC retention time=4.51 min.

Workup

  1. stirringunder stirring
  2. stirringThe resulting mixture was stirred for 40 min at room temperature
  3. washThe mixture was washed with water (5 mL)
  4. washwashed with saturated aqueous sodium hydrogencarbonate (5 mL)
  5. customThe organic phase was collected
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum
  9. customThe crude product was purified by preparative HPLC

Sources & evidence

ORD record
ord-68ca62a907c04bdabbb9771cf8a7c76a
Source dataset
uspto-grants-2013_10
Patent number
US08569495B2

Reaction notes

Loading…