Perchloric Acid → HCID 178489411, compound

HRID 886611Notes

Reaction equation

HRID 886611 reaction equation
[OH:1][CH:2]([C:8]1[CH:9]=[N:10][CH:11]=[C:12]([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:13]=1)[C:3]([N:5]([CH3:7])[CH3:6])=[O:4].Cl(O)(=O)(=O)=O>C(O)(=O)C>[OH:1][CH:2]([C:8]1[CH:9]=[N:10][CH:11]=[C:12]([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:13]=1)[C:3]([N:5]([CH3:6])[CH3:7])=[O:4]

Participants

4

Reactant 2

HCID 24247Perchloric AcidHCID 59824997HCID 59824997, compound

Product 1

HCID 178489411HCID 178489411, compoundYield 3.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

2-Hydroxy-2-{5-[3-(2-methoxyphenyl)-1-(2-trimethylsilanylethoxymethyl)-1H-pyrazolo[3,4-b]pyridin5-yl]-pyridin-3-yl}-N,N-dimethylacetamide (374 mg, 0.702 mmol) was treated with 5% v/v of 70% perchloric acid in glacial acetic acid (5 mL) for 2 h. The solids were collected by filtration and were dissolved in ethyl acetate upon shaking with saturated sodium bicarbonate. The layers were separated and the organics were dried over sodium sulfate and concentrated in vacuo. The material was dissolved in dichloromethane (1 mL) and treated with N,N-dimethylethylenediamine (154 μL) for 2.5 h. The mixture was concentrated and the residue was dissolved in dimethylsulfoxide and purified by preparative HPLC to afford 2-hydroxy-2-{5-[3-(2-methoxyphenyl)-1H-pyrazolo[3,4-b]pyridin5-yl]-pyridin-3-yl}-N,N-dimethylacetamide (10 mg, 0.025 mmol). 1H-NMR (500 MHz, dimethylsulfoxide-d6) δ 2.79 (s, 3H), 2.92 (s, 3H), 3.79 (s, 3H), 5.52 (m, 1H), 5.78 (m, 1H), 7.03 (t, J=7.0 Hz, 1H), 7.17 (d, J=8 Hz, 1H), 7.40 (dt, J=1, J=6.5 Hz, 1H), 7.59 (dd, J=1.5, J=7.5 Hz, 1H), 8.04 (t, J=2.5 Hz, 1H), 8.33 (d, J=2.5 Hz, 1H), 8.52 (d, J=2.0 Hz, 1H), 8.81 (d, J=2.0 Hz, 1H), 8.85 (d, J=2.5 Hz, 1H). MS: m/z 404 (M+H+).

Workup

  1. filtrationThe solids were collected by filtration
  2. dissolutionwere dissolved in ethyl acetate
  3. customThe layers were separated
  4. dry with materialthe organics were dried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. dissolutionThe material was dissolved in dichloromethane (1 mL)
  7. additiontreated with N,N-dimethylethylenediamine (154 μL) for 2.5 h
  8. concentrationThe mixture was concentrated
  9. dissolutionthe residue was dissolved in dimethylsulfoxide
  10. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-a17baeaad4b64adcba5d76fa4d87f51d
Source dataset
uspto-grants-2012_08
Patent number
US08242280B2

Reaction notes

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