Trifluoroacetic acid → HCID 78321126, compound

HRID 930314Notes

Reaction equation

HRID 930314 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH3:38])[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].FC(F)(F)C(O)=O>C(Cl)Cl.C([O-])([O-])=O.[Na+].[Na+]>[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[C:5]([CH3:38])=[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

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86732140HCID 86732140, compound

Product 1

HCID 78321126HCID 78321126, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 10340Sodium CarbonateSolvent

Procedure

A solution of tert-butyl ((4S,6S)-4-(6-(5-cyano-3-methylpicolinamido)-3-fluoropyridin-2-yl)-4-methyl-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-2-yl)carbamate (9a, 0.052 g, 0.097 mmol) in DCM (1.5 mL) was treated with trifluoroacetic acid (0.747 mL, 9.69 mmol) and stirred at room temperature for 30 min. The reaction mixture was diluted with aqueous saturated Na2CO3 and extracted with DCM. The organic extract was washed with brine and dried over Na2SO4. The solution was concentrated under reduced pressure and the title compound was obtained as a white solid (40 mg, 95% yield). MS m/z=437 [M+H]+. Calculated for C19H16F4N6O2: 436.

Workup

  1. extractionextracted with DCM
  2. extractionThe organic extract
  3. washwas washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationThe solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-a62f3f219e584047b84408c257a3fd6c
Source dataset
uspto-grants-2016_03
Patent number
US09296734B2

Reaction notes

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