Perchloric Acid → HCID 178496339, compound

HRID 1865665Notes

Reaction equation

HRID 1865665 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-8c9ec166920744a4bca5aa93fd606d01
Source dataset
uspto-grants-2009_12
Patent number
US07626021B2

Reaction notes

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