Trifluoroacetic acid → HCID 178509346, compound

HRID 384081Notes

Reaction equation

HRID 384081 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-3e13d7645f6f459690c8e19cd2c982a1
Source dataset
uspto-grants-2013_02
Patent number
US08367697B2

Reaction notes

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