Hydrochloric Acid → HCID 178489381, compound

HRID 886579Notes

Reaction equation

HRID 886579 reaction equation
[OH:1][CH:2]([C:34]1[C:39]([C:40]([F:43])([F:42])[F:41])=[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.C(N)CN.Cl.C(=O)(O)[O-].[Na+]>C(O)C.[OH-].[Na+].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[C:39]([C:40]([F:43])([F:41])[F:42])=[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

8

Reactant 4

HCID 313Hydrochloric AcidHCID 3301EthylenediamineHCID 516892Sodium BicarbonateHCID 598250482,2-Dimethyl-propionic acid 5-{3-[hydroxy-(3-trifluoromethyl-pyridin-2-yl)-methyl]-phenyl}-3-(2-methoxy-phenyl)-pyrazolo[3,4-b]pyridin-1-ylmethyl ester

Product 1

HCID 178489381HCID 178489381, compoundYield 4%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 6212ChloroformSolventHCID 14798Sodium HydroxideSolvent

Procedure

380 mg (0.64 mmol) of 2,2-dimethyl-propionic acid 5-{3-[hydroxy-(3-trifluoromethyl-pyridin-2-yl)-methyl]-phenyl}-3-(2-methoxy-phenyl)-pyrazolo[3,4-b]pyridin-1-ylmethyl ester was dissolved in hot ethanol. 0.5 ml (450 mg, 7.5 mmol) of ethylene diamine was added and the mixture diluted with 2 M aqueous sodium hydroxide (30% v/v). The resulting mixture was gently heated until all material was dissolved and the solution left at room temperature for 16 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 mass-triggered reverse-phase HPLC to afford 12 mg (25 μmol, 4%) of {3-[3-(2-methoxy-phenyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]-phenyl}-(3-trifluoromethyl-pyridin-2-yl)-methanol as a yellow solid. 1H NMR (500 MHz, DMSO-d6) δ 13.83 (s, 1H), 8.86 (d, 1H), 8.79 (s, 1H), 8.28 (d, 1H), 7.79 (s, 1H), 7.66 (d, 1H), 7.62 (d, 1H), 7.54 (dd, 1H), 7.47 (t, 1H), 7.43 (t, 1H), 7.35 (d, 1H), 7.24 (d, 1H), 7.10 (t, 1H), 6.23 (d, 1H), 6.10 (d, 1H), 3.85 (s, 3H); MS: m/z 477.1 (M+H+).

Workup

  1. temperatureThe resulting mixture was gently heated until all material
  2. dissolutionwas dissolved
  3. extractionThe aqueous layer was extracted three times with chloroform
  4. dry with materialThe combined organic phases were dried over sodium sulfate
  5. customevaporated
  6. customThe residue was purified by mass-triggered reverse-phase HPLC

Sources & evidence

ORD record
ord-269f1fb3f881428985f3baf04edf9313
Source dataset
uspto-grants-2012_08
Patent number
US08242280B2

Reaction notes

Loading…