Dimethylformamide → HCID 24764821, compound

HRID 1095476Notes

Reaction equation

HRID 1095476 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([N:14]2[CH2:19][CH2:18][N:17]([C:20]([CH:22]3[CH2:24][CH2:23]3)=[O:21])[CH2:16][CH:15]2[CH2:25][OH:26])(=[O:13])=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:27]N(C=O)C.CI.[H-].[Na+]>C1COCC1.C([O-])(O)=O.[Na+]>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([N:14]2[CH2:19][CH2:18][N:17]([C:20]([CH:22]3[CH2:23][CH2:24]3)=[O:21])[CH2:16][CH:15]2[CH2:25][O:26][CH3:27])(=[O:12])=[O:13])=[CH:7][CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 24764818HCID 24764818, compound

Product 1

HCID 24764821HCID 24764821, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 516892Sodium BicarbonateSolvent

Procedure

(1-(4-tert-Butylphenylsulfonyl)piperazin-2-yl)methanol (97 mg, 0.255 mmol, 1.0 equiv, prepared as described in example 17) was dissolved in 5 mL THF under N2 followed by the addition of 0.1 mL DMF, 0.079 mL methyl iodide (0.765 mmol, 3.0 equiv) and 18 mg sodium hydride (1.28 mmol, 5.0 equiv). The solution was allowed to stir for one hour, at which time the solution was diluted with a saturated NaHCO3 solution. The resulting solution was extracted (3×CH2Cl2), dried (Na2SO4), and concentrated under reduced pressure. Purification by flash chromatography (SiO2, 0.5-2% MeOH/CH2Cl2) gave the product as a white solid. 1H NMR (DMSO, 400 MHz) δ 7.79 (d, J=8.4 Hz, 2H), 7.63 (d, J=8.5 Hz, 2 H), 4.21-3.90 (m, 3 H), 3.65 (m, 1 H), 3.45-2.65 (m, 8 H), 1.82 (m, 1 H), 1.30 (s, 9 H), 0.683 (broad s, 4 H).

Workup

  1. extractionThe resulting solution was extracted (3×CH2Cl2)
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated under reduced pressure
  4. customPurification by flash chromatography (SiO2, 0.5-2% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-fdfb2a1cd8c24d168c3b58109dd94d85
Source dataset
uspto-grants-2012_03
Patent number
US08138190B2

Reaction notes

Loading…