Citric Acid → HCID 178489405, compound

HRID 1865578Notes

Reaction equation

HRID 1865578 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]3[C:16]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=4[O:23][CH3:24])=[N:15][N:14](COCC[Si](C)(C)C)[C:11]3=[N:12][CH:13]=2)=[CH:4][C:3]=1[C:33]([N:35]1[CH2:40][CH2:39][O:38][CH2:37][CH2:36]1)=[O:34].B(F)(F)F.CCOCC.[OH-].[K+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O.S([O-])([O-])(=O)=O.[Na+].[Na+]>ClCCl>[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]3[C:16]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=4[O:23][CH3:24])=[N:15][NH:14][C:11]3=[N:12][CH:13]=2)=[CH:4][C:3]=1[C:33]([N:35]1[CH2:36][CH2:37][O:38][CH2:39][CH2:40]1)=[O:34]

Participants

7

Reactant 5

HCID 311Citric AcidHCID 8000Boron trifluoride etherateHCID 14797Potassium HydroxideHCID 24436Sodium SulfateHCID 68617729{2-hydroxy-5-[3-(2-methoxy-phenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]-phenyl}-morpholin-4-yl-methanone

Product 1

HCID 178489405HCID 178489405, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of {2-hydroxy-5-[3-(2-methoxy-phenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]-phenyl}-morpholin-4-yl-methanone (34 mg, 61 μmol) in dichloromethane (15 mL) was cooled to 0-5° C. and boron trifluoride diethyl etherate (100 μl, 0.8 mmol) was added. The mixture was then stirred at 0-5° C. for 40 min before 10 ml of a 10% (w/v) solution of potassium hydroxide was added. The mixture was further stirred at room temperature for 1 h. The pH was then adjusted to approximately 3-4 by addition of citric acid and the aqueous phase saturated with sodium sulfate. The resulting mixture was extracted dichloromethane (3×). The organic phases were combined, washed with a saturated aqueous solution of sodium bicarbonate, dried over sodium sulfate and evaporated to afford {2-hydroxy-5-[3-(2-methoxy-phenyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]-phenyl}-morpholin-4-yl-methanone (11.5 mg, 44% yield) as a colorless solid. 1H-NMR (500 MHz, d6-DMSO) δ 13.76 (s, 1H), 10.06 (s, 1H), 8.78 (d, 1H), 8.23 (d, 1H), 7.64 (dd, 1H), 7.62 (dd, 1H), 7.51 (d, 1H), 7.46 (ddd, 1H), 7.22 (d, 1H), 7.10 (t, 1H), 6.99 (d, 1H), 3.84 (s, 3H), 3.7-3.2 (m, 8H). MS: m/z 431 [MH+].

Workup

  1. additionwas added
  2. extractionThe resulting mixture was extracted dichloromethane (3×)
  3. washwashed with a saturated aqueous solution of sodium bicarbonate
  4. dry with materialdried over sodium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-4648861dc8e447edbc075af2b1e85575
Source dataset
uspto-grants-2009_12
Patent number
US07626021B2

Reaction notes

Loading…