Trifluoroacetic acid → (1S,6R)-3,8-diazabicyclo[4.2.0]octan-8-yl(3-fluoro-2-(2H-1,2,3-triazol-2-yl)phenyl)methanone

HRID 2175004Notes

Reaction equation

HRID 2175004 reaction equation
[F:1][C:2]1[C:3]([N:25]2[N:29]=[CH:28][CH:27]=[N:26]2)=[C:4]([CH:22]=[CH:23][CH:24]=1)[C:5]([N:7]1[C@H:14]2[C@H:9]([CH2:10][CH2:11][N:12](C(OC(C)(C)C)=O)[CH2:13]2)[CH2:8]1)=[O:6].C(O)(C(F)(F)F)=O>C(Cl)Cl>[C@H:14]12[N:7]([C:5]([C:4]3[CH:22]=[CH:23][CH:24]=[C:2]([F:1])[C:3]=3[N:25]3[N:29]=[CH:28][CH:27]=[N:26]3)=[O:6])[CH2:8][C@H:9]1[CH2:10][CH2:11][NH:12][CH2:13]2

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67086535(1S,6R)-tert-butyl 8-(3-fluoro-2-(2H-1,2,3-triazol-2-yl)benzoyl)-3,8-diazabicyclo[4.2.0]octane-3-carboxylate

Product 1

HCID 67086539(1S,6R)-3,8-diazabicyclo[4.2.0]octan-8-yl(3-fluoro-2-(2H-1,2,3-triazol-2-yl)phenyl)methanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To (1S,6R)-tert-butyl 8-(3-fluoro-2-(2H-1,2,3-triazol-2-yl)benzoyl)-3,8-diazabicyclo[4.2.0]octane-3-carboxylate (656 mg, 1.6 mmol) in CH2Cl2 (10 mL) was added TFA (10 mL). After 3 h, the volatiles were removed via rotovap. The resulting residue was neutralized using 5% Na2CO3 (aq) and extracted with CH2Cl2 (3×). The aqueous layer was saturated with NaCl and extracted with CH2Cl2 (3×). The combined organics were dried (Na2SO4) and concentrated to give the title compound as a yellow foam that was used without further purification. MS (ESI) mass calcd. C15H16FN5O, 301.32; m/z found 302.0 [M+H]+.

Workup

  1. customthe volatiles were removed via rotovap
  2. extractionextracted with CH2Cl2 (3×)
  3. extractionextracted with CH2Cl2 (3×)
  4. dry with materialThe combined organics were dried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-ecc6534998764bffa200f0c056eb74f3
Source dataset
uspto-grants-2015_06
Patent number
US09062044B2

Reaction notes

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