HCID 59836036, compound → HCID 178489377, compound

HRID 2389008Notes

Reaction equation

HRID 2389008 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[C:17]2[C:12](=[N:13][CH:14]=[C:15]([C:18]3[CH:19]=[C:20]([CH:23]=[CH:24][CH:25]=3)[C:21]#[N:22])[CH:16]=2)[N:11](COCC[Si](C)(C)C)[N:10]=1>FC(F)(F)C(O)=O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[C:17]2[C:12](=[N:13][CH:14]=[C:15]([C:18]3[CH:19]=[C:20]([CH:23]=[CH:24][CH:25]=3)[C:21]#[N:22])[CH:16]=2)[NH:11][N:10]=1

Participants

3

Reactant 1

HCID 59836036HCID 59836036, compound

Product 1

HCID 178489377HCID 178489377, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

3-[3-(2-Methoxy-phenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]-benzonitrile (22 mg, 0.048 mmol) was dissolved in 1 mL trifluoroacetic acid. The mixture was stirred at room temperature for 1 h and the solvent was evaporated. The crude product was dissolved in 1 mL of methanol and 50 μL of ethylenediamine was added. After 15 min., mL of DMSO was added and the mixture was directly purified by mass-triggered preparative reverse phase HPLC to give 3-[3-(2-methoxy-phenyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]-benzonitrile as a colorless solid (4.6 mg, 30% yield). 1H NMR (500 MHz, DMSO-d6) δ 8.90 (d, J=2.5 Hz, 1H), 8.44 (d, J=2.5 Hz, 1H), 8.28 (t, J=2 Hz, 1H), 8.12 (m, 2H), 7.84 (dt, J1=8 Hz, J2=1 Hz, 1H), 7.67 (t, J=7.5 Hz, 1H), 7.64 (dd, J1=7.5 Hz, J2=2 Hz, 1H), 7.46 (m, 1H), 7.21 (d, J=8 Hz, 1H), 7.09 (td, J1=7.5 Hz, J2=1 Hz, 1H), 3.83 (s, 3H); MS: m/z 327 [MH+].

Workup

  1. customthe solvent was evaporated
  2. dissolutionThe crude product was dissolved in 1 mL of methanol
  3. addition50 μL of ethylenediamine was added
  4. waitAfter 15 min.
  5. additionmL of DMSO was added
  6. customthe mixture was directly purified by mass-triggered preparative reverse phase HPLC

Sources & evidence

ORD record
ord-366979a3a41044dabe663679ed4ab9a4
Source dataset
uspto-grants-2012_09
Patent number
US08268994B2

Reaction notes

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