Triethyloxonium tetrafluoroborate → HCID 68157194, compound

HRID 243195Notes

Reaction equation

HRID 243195 reaction equation
F[B-](F)(F)F.C([O+](CC)CC)C.[C:13]([O:17][C:18](=[O:25])[NH:19][C@H:20]([C:22](=O)[NH2:23])[CH3:21])([CH3:16])([CH3:15])[CH3:14].[F:26][C:27]1[CH:28]=[C:29]([NH:34][C:35]2[N:36]([CH3:40])[N:37]=[CH:38][CH:39]=2)[C:30](N)=[CH:31][CH:32]=1>C(Cl)Cl>[C:13]([O:17][C:18](=[O:25])[NH:19][C@H:20]([C:22]1[N:34]([C:35]2[N:36]([CH3:40])[N:37]=[CH:38][CH:39]=2)[C:29]2[CH:28]=[C:27]([F:26])[CH:32]=[CH:31][C:30]=2[N:23]=1)[CH3:21])([CH3:16])([CH3:15])[CH3:14]

Participants

5

Reactant 3

HCID 2723982Triethyloxonium tetrafluoroborateHCID 7015295Boc-Ala-NH2HCID 68157564HCID 68157564, compound

Product 1

HCID 68157194HCID 68157194, compoundYield 130.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethyloxonium tetrafluoroborate (1.06 g, 5.60 mmol) was added to a solution of ((S)-1-carbamoylethyl)carbamic acid tert-butyl ester (1.26 g, 6.67 mmol) in DCM (20 mL) at 20° C. under nitrogen and the resultant mixture stirred for 3 h then concentrated in vacuo. The resultant residue was dissolved in ethanol (20 mL) and 4-fluoro-N2-(2-methyl-2H-pyrazol-3-yl)-benzene-1,2-diamine (0.55 g, 2.67 mmol) added, and the reaction mixture stirred at reflux for 16 h under nitrogen. The reaction mixture was concentrated in vacuo and residue partitioned between DCM (×3) and saturated aqueous NaHCO3. The combined DCM extracts were dried (Na2SO4) and concentrated in vacuo. The resultant residue was purified by chromatography (SiO2, 0-5% (2M ammonia in methanol) in DCM) to give the title compound as a yellow oil (1.25 g, 100%). LCMS (Method C): RT 3.08 min [M+H]+ 360.2. 310091751

Workup

  1. concentrationthen concentrated in vacuo
  2. dissolutionThe resultant residue was dissolved in ethanol (20 mL)
  3. temperatureat reflux for 16 h under nitrogen
  4. concentrationThe reaction mixture was concentrated in vacuo and residue
  5. custompartitioned between DCM (×3) and saturated aqueous NaHCO3
  6. dry with materialThe combined DCM extracts were dried (Na2SO4)
  7. concentrationconcentrated in vacuo
  8. customThe resultant residue was purified by chromatography (SiO2, 0-5% (2M ammonia in methanol) in DCM)

Sources & evidence

ORD record
ord-2c27b7ddfe614bdf9b04354ad4167d45
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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