Trifluoroacetic acid → HCID 178507129, compound

HRID 221999Notes

Reaction equation

HRID 221999 reaction equation
[F:1][C:2]1([F:40])[CH2:5][C:4]([NH:32]C(=O)OC(C)(C)C)([C:6]2[CH:11]=[CH:10][C:9]([C:12]3[C:21]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)=[CH:20][C:19]4[C:18]5=[N:28][N:29]=[C:30]([OH:31])[N:17]5[CH:16]=[CH:15][C:14]=4[N:13]=3)=[CH:8][CH:7]=2)[CH2:3]1.C(O)(C(F)(F)F)=O>C(Cl)(Cl)Cl>[NH2:32][C:4]1([C:6]2[CH:7]=[CH:8][C:9]([C:12]3[C:21]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)=[CH:20][C:19]4[C:18]5=[N:28][N:29]=[C:30]([OH:31])[N:17]5[CH:16]=[CH:15][C:14]=4[N:13]=3)=[CH:10][CH:11]=2)[CH2:5][C:2]([F:1])([F:40])[CH2:3]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178452598HCID 178452598, compound

Product 1

HCID 178507129HCID 178507129, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a mixture of tert-butyl {3,3-difluoro-1-[4-(3-hydroxy-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl)phenyl]cyclobutyl}carbamate (5-20) (11 mg, 0.021 mmol) in CHCl3 (0.5 mL) was added TFA (0.5 mL), and the mixture was stirred at room temperature for 1 hour. The solvent was concentrated under reduced pressure and the residue was purified by reverse phase column chromatography (Sunfire C18) eluting with 5 to 95% acetonitrile/(0.1% TFA/water) gradient. The appropriate fractions were free based by suspending in ethyl acetate, washed with a saturated solution of sodium bicarbonate, followed by water, brine, dried over sodium sulfate, filtered, and concentrated in vacuo to give 8-[4-(1-amino-3,3-difluorocyclobutyl)phenyl]-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-3-ol (5-21) as a yellow oil. HRMS (M+H)+: observed=444.1636, calculated=444.1653.

Workup

  1. concentrationThe solvent was concentrated under reduced pressure
  2. customthe residue was purified by reverse phase column chromatography (Sunfire C18)
  3. washeluting with 5 to 95% acetonitrile/(0.1% TFA/water) gradient
  4. washwashed with a saturated solution of sodium bicarbonate
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8e1f08f98e91477f8ce716ce0c0d4b86
Source dataset
uspto-grants-2012_06
Patent number
US08207169B2

Reaction notes

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