Trifluoroacetic acid → HCID 77461103, compound

HRID 930308Notes

Reaction equation

HRID 930308 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]([C:9]([NH:11][C:12]2[N:17]=[C:16]([C@:18]3([CH3:36])[CH2:23][C@@H:22]([C:24]([F:27])([F:26])[F:25])[O:21][C:20]([NH:28]C(=O)OC(C)(C)C)=[N:19]3)[C:15]([F:37])=[CH:14][CH:13]=2)=[O:10])=[N:7][CH:8]=1)#[N:2].C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:28][C:20]1[O:21][C@H:22]([C:24]([F:25])([F:27])[F:26])[CH2:23][C@:18]([C:16]2[N:17]=[C:12]([NH:11][C:9](=[O:10])[C:6]3[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:8][N:7]=3)[CH:13]=[CH:14][C:15]=2[F:37])([CH3:36])[N:19]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86732137HCID 86732137, compound

Product 1

HCID 77461103HCID 77461103, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl ((4S,6S)-4-(6-(5-cyanopicolinamido)-3-fluoropyridin-2-yl)-4-methyl-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-2-yl)carbamate (7l, 0.096 g, 0.18 mmol) in DCM (3 mL) was added TFA (1 mL). The reaction mixture was stirred at room temperature for 1 h and the solvent was removed under reduced pressure. The residue was treated with 1 N NaOH (5 mL) and extracted with DCM (3×5 mL). The combined organic extracts were dried over sodium sulfate and concentrated under reduced pressure. The crude material was triturated with ether and the solid was filtered off to give the title compound as a white solid (0.065 g, 84% yield, 0.15 mmol) after drying under vacuum. MS m/z=423.0 [M+H]+. Calculated for C18H14F4N6O2: 422

Workup

  1. customthe solvent was removed under reduced pressure
  2. additionThe residue was treated with 1 N NaOH (5 mL)
  3. extractionextracted with DCM (3×5 mL)
  4. dry with materialThe combined organic extracts were dried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe crude material was triturated with ether
  7. filtrationthe solid was filtered off

Sources & evidence

ORD record
ord-8032e1608e604c7aa54e81b48c0846f5
Source dataset
uspto-grants-2016_03
Patent number
US09296734B2

Reaction notes

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