Hydrochloric Acid → HCID 59769921, compound

HRID 2218721Notes

Reaction equation

HRID 2218721 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]=[CH: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]=[CH: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 59769968HCID 59769968, compound

Product 1

HCID 59769921HCID 59769921, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Mix 6-(10,11-dihydro-dibenzo[a,d]cyclohepten-5-ylidenemethyl)-pyridin-2-ylamine (70 mg, 0.235 mmol), triethylamine (68 μL, 0.470 mmol), N,N-dimethylaminopyridine (3 mg, 0.024 mmol), and methanesulfonyl chloride (19 μL, 0.247 mmol) in CH2Cl2 (2 mL). Stir at room temperature overnight and add 150 □L 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 (0.25 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 (10 g), eluting with 20% to 35% ethyl acetate/hexanes to afford 61 mg (69%) of the title compound as a yellow oil. MS (ES) 377 (M+H), 375 (M−H); BPLC shows 96% 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 (0.25 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 (10 g), eluting with 20% to 35% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-48735d8dd1b54122a5e977d2041bf260
Source dataset
uspto-grants-2008_08
Patent number
US07411072B2

Reaction notes

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