Trifluoroacetic acid → HCID 178489383, compound

HRID 886587Notes

Reaction equation

HRID 886587 reaction equation
[OH:1][CH:2]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]2[CH:15]=[C:16]3[C:22]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=4[O:29][CH3:30])=[N:21][N:20](COCC[Si](C)(C)C)[C:17]3=[N:18][CH:19]=2)[CH:9]=1)[C:3]([N:5]([CH3:7])[CH3:6])=[O:4].FC(F)(F)C(O)=O>>[OH:1][CH:2]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]2[CH:15]=[C:16]3[C:22]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=4[O:29][CH3:30])=[N:21][NH:20][C:17]3=[N:18][CH:19]=2)[CH:9]=1)[C:3]([N:5]([CH3:7])[CH3:6])=[O:4]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 598250912-hydroxy-2-{3-[3-(2-methoxy-phenyl)-1-(2-trimethylsilanylethoxymethyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]-phenyl}-N,N-dimethyl-acetamide

Product 1

HCID 178489383HCID 178489383, compound

Procedure

To the crude 2-hydroxy-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 trifluoroacetic acid (2 mL) and the resulting mixture was sonicated until the residue was completely dissolved. The trifluoroacetic acid was evaporated and the residue treated with ethylene diamine (0.2 mL). The resulting mixture was purified via mass-triggered reverse-phase HPLC to yield 2-hydroxy-2-{3-[3-(2-methoxy-phenyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]-phenyl}-N,N-dimethyl-acetamide as a white solid (25 mg, 33% over two steps). MS: m/z 403 (M+H+). 1H NMR (500 MHz, DMSO-d6) δ 2.89 (d, 6H), 3.87 (s, 3H), 5.48 (d, 1H), 5.57 (d, 1H), 7.10 (t, 1H), 7.24 (d, 1H), 7.38 (d, 1H), 7.47 (dt, 1H), 7.48 (t, 1H), 7.67 (dd, 1H), 7.70 (d, 1H), 7.75 (s, 1H), 8.32 (d, 1H), 8.84 (d, 1H), 13.84 (s, 1H).

Workup

  1. customthe resulting mixture was sonicated until the residue
  2. dissolutionwas completely dissolved
  3. customThe trifluoroacetic acid was evaporated
  4. additionthe residue treated with ethylene diamine (0.2 mL)
  5. customThe resulting mixture was purified via mass-triggered reverse-phase HPLC

Sources & evidence

ORD record
ord-527335f25f5b4fec85d5ac2785ec1185
Source dataset
uspto-grants-2012_08
Patent number
US08242280B2

Reaction notes

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