Hydrochloric Acid → HCID 178489379, compound

HRID 886578Notes

Reaction equation

HRID 886578 reaction equation
[OH:1][CH:2]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][N:35]=1)[C:3]1[CH:4]=[C:5]([C:9]2[CH:10]=[C:11]3[C:17]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=4[O:24][CH3:25])=[N:16][N:15](COC(=O)C(C)(C)C)[C:12]3=[N:13][CH:14]=2)[CH:6]=[CH:7][CH:8]=1.[OH-].[Na+].Cl.C(=O)(O)[O-].[Na+]>C(O)C.C(Cl)(Cl)Cl>[CH3:25][O:24][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[C:17]1[C:11]2[C:12](=[N:13][CH:14]=[C:9]([C:5]3[CH:4]=[C:3]([CH:2]([C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][N:35]=4)[OH:1])[CH:8]=[CH:7][CH:6]=3)[CH:10]=2)[NH:15][N:16]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 59825052HCID 59825052, compound

Product 1

HCID 178489379HCID 178489379, compoundYield 43%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6212ChloroformSolvent

Procedure

200 mg (0.38 mmol) of 2,2-dimethyl-propionic acid 5-[3-(hydroxy-pyridin-2-yl-methyl)-phenyl]-3-(2-methoxy-phenyl)-pyrazolo[3,4-b]pyridin-1-ylmethyl ester was dissolved in 10 mL of ethanol. 10 mL of 2 M aqueous sodium hydroxide was added and the resulting mixture was left at room temperature for 5 h. The pH was adjusted to 8 by addition of concentrated aqueous hydrochloric acid and the resulting solution was distributed between chloroform and saturated aqueous sodium bicarbonate. The aqueous layer was extracted three times with chloroform. The combined organic phases were dried over sodium sulfate and evaporated. The residue was purified by flash chromatography on silica gel using a gradient of ethyl acetate in hexanes and then by mass-triggered reverse-phase HPLC to afford 67 mg (0.16 mmol, 43%) of {3-[3-(2-methoxy-phenyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]-phenyl}-pyridin-2-yl-methanol as an off-white solid. 1H NMR (500 MHz, DMSO-d6) α 13.84 (s, br., 1H), 8.80 (d, 1H), 8.46 (ddd, 1H), 8.28 (d, 1H), 7.80 (ddd, 1H), 7.77 (m, 1H), 7.67 (dd, 1), 7.64 (d, 1H), 7.61 (m, 1H), 7.47 (ddd, 1H), 7.43-7.42 (m, 2H), 7.24 (d, 1H), 7.23 (dd(d), 1H), 7.10 (ddd, 1H), 6.19 (s, br., 1H), 5.82 (s, br., 1H) 3.86 (s, 3H); MS: m/z 409.1 (M+H+).

Workup

  1. extractionThe aqueous layer was extracted three times with chloroform
  2. dry with materialThe combined organic phases were dried over sodium sulfate
  3. customevaporated
  4. customThe residue was purified by flash chromatography on silica gel using a gradient of ethyl acetate in hexanes

Sources & evidence

ORD record
ord-201c4933be1d45e9bf2a3082db1973d5
Source dataset
uspto-grants-2012_08
Patent number
US08242280B2

Reaction notes

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