Trifluoroacetic acid → HCID 178509346, compound

HRID 1920869Notes

Reaction equation

HRID 1920869 reaction equation
[F:1][C:2]([F:51])([F:50])[C:3]1[C:11]2[C:6](=[N:7][CH:8]=[CH:9][C:10]=2[C:12]2[CH:13]=[C:14]([C:18]3([CH2:22][NH:23]C(=O)OC(C)(C)C)[CH2:21][O:20][CH2:19]3)[CH:15]=[CH:16][CH:17]=2)[N:5](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[N:4]=1.C([SiH](CC)CC)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:50][C:2]([F:1])([F:51])[C:3]1[C:11]2[C:6](=[N:7][CH:8]=[CH:9][C:10]=2[C:12]2[CH:13]=[C:14]([C:18]3([CH2:22][NH2:23])[CH2:19][O:20][CH2:21]3)[CH:15]=[CH:16][CH:17]=2)[NH:5][N:4]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 67492851HCID 67492851, compound

Product 1

HCID 178509346HCID 178509346, compoundYield 26.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

tert-Butyl N-[[3-[3-[3-(trifluoromethyl)-1-trityl-pyrazolo[3,4-b]pyridin-4-yl]phenyl]oxetan-3-yl]methyl]carbamate (58 mg, 0.08397 mmol) was dissolved in DCM (2 mL) and cooled to 0° C. Triethylsilane (39.06 mg, 53.65 μL, 0.3359 mmol) was added followed by TFA (0.5 mL). The reaction was stirred at 0° C. for 1 hour then the solvent removed under reduced pressure. The crude product was dissolved in DMSO and purified by FractionLynx. The fractions were passed through bicarbonate cartridges to obtain free base and lyophilised to give (3-(3-(3-(trifluoromethyl)-1H-pyrazolo[3,4-b]pyridin-4-yl)phenyl)oxetan-3-yl)methanamine (7.8 mg, 25%).

Workup

  1. customthe solvent removed under reduced pressure
  2. dissolutionThe crude product was dissolved in DMSO
  3. custompurified by FractionLynx
  4. customto obtain free base

Sources & evidence

ORD record
ord-bf9cfd61d38c442f8d39f0a04073ba7c
Source dataset
uspto-grants-2012_05
Patent number
US08173635B2

Reaction notes

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