Perchloric Acid → HCID 178496339, compound

HRID 2389002Notes

Reaction equation

HRID 2389002 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6](=[O:44])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([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:10][C:9]=1[C:39](=[O:43])[N:40]([CH3:42])[CH3:41].Cl(O)(=O)(=O)=O.C(=O)(O)[O-].[Na+]>C(O)(=O)C>[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6](=[O:44])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([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:10][C:9]=1[C:39](=[O:43])[N:40]([CH3:42])[CH3:41]

Participants

5

Reactant 3

HCID 24247Perchloric AcidHCID 516892Sodium BicarbonateHCID 57975846HCID 57975846, compound

Product 1

HCID 178496339HCID 178496339, compoundYield 55.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To {2-dimethylcarbamoyl-4-[3-(2-methoxy-phenyl)-1-(2-trimethylsilanyl-ethoxy-methyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]-phenyl}-carbamic acid 2-methoxy-ethyl ester (53 mg, 0.084 mmol) was added 5% v/v 70% perchloric acid in acetic acid (0.5 mL) and the resulting solution was agitated for 60 min. Saturated sodium bicarbonate (2 mL) was added and the resulting mixture was extracted with ethyl acetate (3×2 mL). The combined organic layers were concentrated and the residue was purified by mass-triggered reverse-phase HPLC to give {2-dimethylcarbamoyl-4-[3-(2-methoxy-phenyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]-phenyl}-carbamic acid 2-methoxy-ethyl ester as a white solid (23 mg, 55%). MS: m/z 490 (M+H+). 1H NMR (500 MHz, DMSO-d6) δ 3.00 (s, 6H), 3.33 (s, 3H), 3.60 (t, 2H), 3.86 (s, 3H), 4.23 (t, 3H), 7.11 (t, 1H), 7.22 (d, 1H), 7.46 (t, 1H), 7.62 (s, 1H), 7.69 (d, 1H), 7.75 (d, 1H), 7.85 (d, 1H), 8.31 (s, 1H), 8.82 (s, 1H), 13.42 (br, 1H).

Workup

  1. extractionthe resulting mixture was extracted with ethyl acetate (3×2 mL)
  2. concentrationThe combined organic layers were concentrated
  3. customthe residue was purified by mass-triggered reverse-phase HPLC

Sources & evidence

ORD record
ord-635e183d187341688c5b50b414a98d8f
Source dataset
uspto-grants-2012_09
Patent number
US08268994B2

Reaction notes

Loading…