Hydrochloric Acid → HCID 59770233, compound

HRID 2218722Notes

Reaction equation

HRID 2218722 reaction equation
[CH:1]1[C:11]2[CH2:10][CH2:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[C:6](=[CH:16][C:17]3[N:22]=[C:21]([NH2:23])[CH:20]=[N:19][CH:18]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[CH3:31][S:32](Cl)(=[O:34])=[O:33].Cl>C(Cl)Cl>[CH:12]1[C:8]2[CH2:9][CH2:10][C:11]3[CH:1]=[CH:2][CH:3]=[CH:4][C:5]=3[C:6](=[CH:16][C:17]3[N:22]=[C:21]([NH:23][S:32]([CH3:31])(=[O:34])=[O:33])[CH:20]=[N:19][CH:18]=3)[C:7]=2[CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471Triethylamine2×HCID 31297Methanesulfonyl chloride2×HCID 59769989HCID 59769989, compound

Product 1

HCID 59770233HCID 59770233, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Mix 6-(10,11-dihydro-dibenzo[a,d]cyclohepten-5-ylidenemethyl)-pyrazin-2-ylamine (35 mg, 0.117 mmol), triethylamine (34 μL, 0.234 mmol), N,N-dimethylaminopyridine (2 mg, 0.018 mmol), and methanesulfonyl chloride (10 μL, 0.123 mmol) in CH2Cl2 (2 mL). Stir at room temperature overnight and add 150 μL triethylamine and 40 μL methanesulfonyl chloride. Stir at room temperature for 6 h and add 1.00N aqueous HCl (1 mL). Load mixture onto a Varian ChemElut CE1005 solid-phase extraction cartridge, then elute, collect, and concentrate 45 mL CH2Cl2. Dissolve crude product in THF (5 mL), add 1.0M tetrabutylammonium fluoride (0.30 mL), and heat to reflux for 1 h. Cool to room temperature and dilute with H2O and brine. Extract into ethyl acetate, dry (MgSO4) and concentrate organics. Chromatograph on silica gel (4 g), eluting with 20%→35% ethyl acetate/hexanes to afford 19 mg (43%) of the title compound as a white solid. MS (ES) 378 (M+H), 376 (M−H); HPLC shows 100% purity.

Workup

  1. stirringStir at room temperature for 6 h
  2. extractionLoad mixture onto a Varian ChemElut CE1005 solid-phase extraction cartridge
  3. washelute
  4. customcollect
  5. concentrationconcentrate 45 mL CH2Cl2
  6. dissolutionDissolve crude product in THF (5 mL)
  7. additionadd 1.0M tetrabutylammonium fluoride (0.30 mL)
  8. temperatureheat
  9. temperatureto reflux for 1 h
  10. temperatureCool to room temperature
  11. additiondilute with H2O and brine
  12. extractionExtract into ethyl acetate
  13. dry with materialdry (MgSO4)
  14. concentrationconcentrate organics
  15. washChromatograph on silica gel (4 g), eluting with 20%→35% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-0c2fc581890a4261a4645ead50ecb8f7
Source dataset
uspto-grants-2008_08
Patent number
US07411072B2

Reaction notes

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