Trifluoroacetic acid → (1S,6R)-3,8-Diazabicyclo[4.2.0]octan-8-yl(2-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl)methanone

HRID 2174984Notes

Reaction equation

HRID 2174984 reaction equation
[CH3:1][C:2]1[N:6]=[C:5]([C:7]2[CH:29]=[CH:28][CH:27]=[CH:26][C:8]=2[C:9]([N:11]2[C@H:18]3[C@H:13]([CH2:14][CH2:15][N:16](C(OC(C)(C)C)=O)[CH2:17]3)[CH2:12]2)=[O:10])[O:4][N:3]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[C@H:18]12[N:11]([C:9]([C:8]3[CH:26]=[CH:27][CH:28]=[CH:29][C:7]=3[C:5]3[O:4][N:3]=[C:2]([CH3:1])[N:6]=3)=[O:10])[CH2:12][C@H:13]1[CH2:14][CH2:15][NH:16][CH2:17]2

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 131732983(1S,6R)-tert-Butyl 8-(2-(3-methyl-1,2,4-oxadiazol-5-yl)benzoyl)-3,8-diazabicyclo[4.2.0]octane-3-carboxylate

Product 1

HCID 67086669(1S,6R)-3,8-Diazabicyclo[4.2.0]octan-8-yl(2-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl)methanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The product of Step B (645 mg, 1.63 mmol), DCM (8 mL), TFA (3 mL) were stirred at room temperature for 2 h and then concentrated in vacuo. The residue was dissolved in DCM and treated with Dowex 550 A resin. After stirring for 2 h the resin was removed by filtration and the filtrate was concentrated in vacuo to a colorless oil which was taken on to the next step without further purification. MS (ESI) mass calculated for C16H18N4O2, 298.14; m/z found, 299.1.

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in DCM
  3. additiontreated with Dowex 550 A resin
  4. customwas removed by filtration
  5. concentrationthe filtrate was concentrated in vacuo to a colorless oil which
  6. customwas taken on to the next step without further purification

Sources & evidence

ORD record
ord-ec44707e7b8f43adb6b382f3e2bed8f4
Source dataset
uspto-grants-2015_06
Patent number
US09062044B2

Reaction notes

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