Triethylamine → HCID 59770506, compound

HRID 2218723Notes

Reaction equation

HRID 2218723 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[CH:22]=[C:21]([NH2:23])[CH:20]=[CH:19][N: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]>C(Cl)Cl.O>[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[CH:22]=[C:21]([NH:23][S:32]([CH3:31])(=[O:34])=[O:33])[CH:20]=[CH:19][N:18]=3)[C:7]=2[CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 59770278HCID 59770278, compound

Product 1

HCID 59770506HCID 59770506, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Mix 2-(10,11-dihydro-dibenzo[a,d]cyclohepten-5-ylidenemethyl)-pyridin-4-ylamine (176 mg, 0.590 mmol), triethylamine (600 μL, 4.13 mmol), N,N-dimethylaminopyridine (7 mg, 0.059 mmol), and methanesulfonyl chloride (137 μL, 1.769 mmol) in CH2Cl2 (10 mL). Stir at room temperature for 3 h and dilute with H2O (15 mL). Extract into CH2Cl2, dry (MgSO4) and concentrate organics. Dissolve crude product in THF (10 mL), add 1.0M tetrabutylammonium fluoride (0.89 mL), and heat to reflux for 4 h. Cool to room temperature and dilute with H2O. Extract into ethyl acetate, dry (MgSO4) and concentrate organics. Chromatograph on silica gel (10 g), eluting with 80% →90% ethyl acetate/hexanes to afford 150 mg (68%) of the title compound as a yellow foam. MS (ES) 377 (M+H), 375 (M−H); BPLC shows 96% purity.

Workup

  1. extractionExtract into CH2Cl2
  2. dry with materialdry (MgSO4)
  3. concentrationconcentrate organics
  4. dissolutionDissolve crude product in THF (10 mL)
  5. additionadd 1.0M tetrabutylammonium fluoride (0.89 mL)
  6. temperatureheat
  7. temperatureto reflux for 4 h
  8. temperatureCool to room temperature
  9. additiondilute with H2O
  10. extractionExtract into ethyl acetate
  11. dry with materialdry (MgSO4)
  12. concentrationconcentrate organics
  13. washChromatograph on silica gel (10 g), eluting with 80% →90% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-59e5ff3e5ce745639b7e61f4370108fc
Source dataset
uspto-grants-2008_08
Patent number
US07411072B2

Reaction notes

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