Triethyloxonium tetrafluoroborate → HCID 68157081, compound

HRID 243146Notes

Reaction equation

HRID 243146 reaction equation
[C:1]([NH:8][C@H:9]([C:11](N)=O)[CH3:10])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].F[B-](F)(F)F.C([O+](CC)CC)C.[F:26][C:27]1[CH:28]=[C:29]([NH:34][C:35]2[CH:39]=[CH:38][N:37]([CH3:40])[N:36]=2)[C:30]([NH2:33])=[CH:31][CH:32]=1>C(Cl)Cl.CCO>[C:4]([O:3][C:1](=[O:2])[NH:8][C@H:9]([C:10]1[N:34]([C:35]2[CH:39]=[CH:38][N:37]([CH3:40])[N:36]=2)[C:29]2[CH:28]=[C:27]([F:26])[CH:32]=[CH:31][C:30]=2[N:33]=1)[CH3:11])([CH3:7])([CH3:6])[CH3:5]

Participants

6

Reactant 3

HCID 2723982Triethyloxonium tetrafluoroborateHCID 7015295Boc-Ala-NH2HCID 68157152HCID 68157152, compound

Product 1

HCID 68157081HCID 68157081, compoundYield 31%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a suspension of (S)-Boc-alaninamide (614 mg, 3.27 mmol) in DCM (5 mL) was added triethyloxonium tetrafluoroborate (621 mg, 3.27 mmol) in one portion under a nitrogen atmosphere. The resulting mixture stirred at RT for 1 h. The volatiles were removed in vacuo and to the resulting residue was added 4-fluoro-N2-(1-methyl-1H-pyrazol-3-yl)-benzene-1,2-diamine (350 mg, 1.70 mmol) in absolute EtOH (5 mL) and the mixture stirred at 80° C. for 2 h. The volatiles were removed in vacuo and the resulting residue partitioned between DCM and an aqueous solution of NaHCO3. The organic fraction was dried, concentrated in vacuo and the resulting residue purified by column chromatography (Si—PCC, gradient 0-50% EtOAc in DCM) to afford the title compound as a purple oil (187 mg, 31%). LCMS (Method B): RT 3.18 min [M+H]+ 360.05

Workup

  1. customThe volatiles were removed in vacuo and to the resulting residue
  2. stirringthe mixture stirred at 80° C. for 2 h
  3. customThe volatiles were removed in vacuo
  4. customthe resulting residue partitioned between DCM
  5. customThe organic fraction was dried
  6. concentrationconcentrated in vacuo
  7. customthe resulting residue purified by column chromatography (Si—PCC, gradient 0-50% EtOAc in DCM)

Sources & evidence

ORD record
ord-fdf226689ee94c65bdb653391437c034
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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