Triethylamine → HCID 66744626, compound

HRID 1959365Notes

Reaction equation

HRID 1959365 reaction equation
[CH2:1]([S:3](Cl)(=[O:5])=[O:4])[CH3:2].[C:7]1([C:13]2[O:17][C:16]([C:18]3[C:19]([NH2:30])=[N:20][CH:21]=[C:22]([N:24]4[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]4)[N:23]=3)=[N:15][N:14]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(N(CC)CC)C>ClCCl>[CH2:1]([S:3]([N:27]1[CH2:28][CH2:29][N:24]([C:22]2[N:23]=[C:18]([C:16]3[O:17][C:13]([C:7]4[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=4)=[N:14][N:15]=3)[C:19]([NH2:30])=[N:20][CH:21]=2)[CH2:25][CH2:26]1)(=[O:5])=[O:4])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 11667Ethanesulfonyl chlorideHCID 667444203-(5-Phenyl-1,3,4-oxadiazol-2-yl)-5-(piperazin-1-yl)pyrazin-2-amine

Product 1

HCID 66744626HCID 66744626, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Ethanesulfonyl chloride (37.51 mg, 27.64 μL, 0.2917 mmol) was added to a solution of 3-(5-phenyl-1,3,4-oxadiazol-2-yl)-5-piperazin-1-yl-pyrazin-2-amine (116 mg, 0.2652 mmol) and triethylamine (53.67 mg, 73.93 μL, 0.5304 mmol) in dichloromethane (5 mL) at 0° C. and the resulting solution stirred at room temperature for 1.5 hours. The mixture was diluted with dichloromethane, washed with water and the aqueous layer extracted further with dichloromethane. The organics were washed with saturated aqueous NaHCO3, dried over MgSO4 and concentrated in vacuo. The resultant residue was purified on silica gel by flash column chromatography (3% MeOH/DCM) to afford the title compound still impure. This was purified by reverse phase preparative HPLC [Waters Sunfire C18, 10 uM, 100A column, gradient 10%-95% B (solvent A: 0.05% TFA in water, solvent B: CH3CN) over 16 minutes at 25 mL/min]. The fractions were collected and freeze-dried to give the title compound (25.2 mg, 18% Yield).

Workup

  1. washwashed with water
  2. extractionthe aqueous layer extracted further with dichloromethane
  3. washThe organics were washed with saturated aqueous NaHCO3
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe resultant residue was purified on silica gel by flash column chromatography (3% MeOH/DCM)

Sources & evidence

ORD record
ord-6923a81db72d4a1fa22eb05ba4e92317
Source dataset
uspto-grants-2013_04
Patent number
US08410112B2

Reaction notes

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