Triethylamine → HCID 46199087, compound

HRID 1959369Notes

Reaction equation

HRID 1959369 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[C:11]([NH2:22])=[N:12][CH:13]=[C:14]([N:16]2[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]2)[N:15]=1.CCN(CC)CC.[CH2:30]([S:32](Cl)(=[O:34])=[O:33])[CH3:31]>C(Cl)Cl>[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[C:11]([NH2:22])=[N:12][CH:13]=[C:14]([N:16]2[CH2:17][CH2:18][N:19]([S:32]([CH2:30][CH3:31])(=[O:34])=[O:33])[CH2:20][CH2:21]2)[N:15]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 11667Ethanesulfonyl chlorideHCID 66745292HCID 66745292, compound

Product 1

HCID 46199087HCID 46199087, compoundYield 65.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

3-(1H-benzo[d]imidazol-2-yl)-5-(piperazin-1-yl)pyrazin-2-amine (50 mg, 0.169 mmol) was dissolved in DCM (3 mL) and Et3N (70.0 μL, 0.507 mmol) followed by ethanesulfonyl chloride (17.6 μL, 0.186 mmol) were added. The reaction was allowed to stir for 30 mins and then diluted with dichloromethane and washed with water. The aqueous layer was extracted further with dichloromethane and the organics washed with saturated aqueous NaHCO3, dried over MgSO4 and concentrated in vacuo. The resultant residue was purified on silica gel by flash column chromatography (0-5% MeOH/DCM) to afford the title compound (42.6 mg, 65% Yield). MS (ES+) 388.0

Workup

  1. additionwere added
  2. washwashed with water
  3. extractionThe aqueous layer was extracted further with dichloromethane
  4. washthe organics washed with saturated aqueous NaHCO3
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe resultant residue was purified on silica gel by flash column chromatography (0-5% MeOH/DCM)

Sources & evidence

ORD record
ord-ad91f606c78c4a24a70c5c817975f5e8
Source dataset
uspto-grants-2013_04
Patent number
US08410112B2

Reaction notes

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