Trifluoroacetic acid → HCID 178489375, compound

HRID 1865668Notes

Reaction equation

HRID 1865668 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]([CH2:24][C:25]([N:27]([CH3:29])[CH3:28])=[O:26])[CH:21]=[CH:22][CH:23]=3)[CH:16]=2)[N:11](COCC[Si](C)(C)C)[N:10]=1.C(O)(C(F)(F)F)=O>CS(C)=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]([CH2:24][C:25]([N:27]([CH3:29])[CH3:28])=[O:26])[CH:21]=[CH:22][CH:23]=3)[CH:16]=2)[NH:11][N:10]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 579757872-{3-[3-(2-Methoxy-phenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]-phenyl}-N,N-dimethyl-acetamide

Product 1

HCID 178489375HCID 178489375, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To the crude 2-{3-[3-(2-methoxy-phenyl)-1-(2-trimethylsilanylethoxymethyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]-phenyl}-N,N-dimethyl-acetamide obtained in last step was added TFA (2 mL) and the resulting mixture was sonicated till the residue was completely dissolved. The TFA was evaporated. The residue was treated with ethylene diamine (0.2 mL) to scavenge the formaldehyde which generated from the de-protection of the trimethylsilanylethoxymethyl group. The resulting mixture was sonicated till the residue was completely dissolved to give a greenish blue solution. DMSO was added to make a 2 mL solution which was used in preparative LCMS purification on a reverse phase column to yield 2-{3-[3-(2-methoxy-phenyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]-phenyl}-N,N-dimethyl-acetamide as a white solid (21 mg, 29% over two steps) MS: m/z 387 (M+H+). 1H NMR (500 MHz, DMSO-d6) δ 2.84 (s, 3H), 3.04 (s, 3H), 3.78 (s, 2H), 3.86 (s, 6H), 7.10 (t, 1H), 7.23 (d, 1H), 7.25 (d, 1H), 7.43 (t, 1H), 7.47 (t, 1H), 7.61 (s, 1H), 7.62 (d, 1H), 7.66 (d, 1H), 8.30 (s, 1H), 8.82 (d, sH), 13.82 (s, 1H).

Workup

  1. customthe resulting mixture was sonicated till the residue
  2. dissolutionwas completely dissolved
  3. customThe TFA was evaporated
  4. additionThe residue was treated with ethylene diamine (0.2 mL)
  5. customThe resulting mixture was sonicated till the residue
  6. dissolutionwas completely dissolved
  7. customto give a greenish blue solution
  8. customwas used in preparative LCMS purification on a reverse phase column

Sources & evidence

ORD record
ord-7fb23a1fdeb743d298dea82669a1edf7
Source dataset
uspto-grants-2009_12
Patent number
US07626021B2

Reaction notes

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