Water → HCID 178433899, compound

HRID 497953Notes

Reaction equation

HRID 497953 reaction equation
[OH:1][C:2]1[C:7]([C:8]([O:10]CC)=O)=[CH:6][N:5]=[C:4]2[N:13]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=3)[N:14]=[C:15]([CH3:16])[C:3]=12.[CH:23]1([NH2:29])[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1.O>C1(C)C(C)=CC=CC=1.CS(C)=O>[CH:23]1([NH:29][C:8]([C:7]2[C:2]([OH:1])=[C:3]3[C:15]([CH3:16])=[N:14][N:13]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=4)[C:4]3=[N:5][CH:6]=2)=[O:10])[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1

Participants

6

Reactant 3

HCID 962WaterHCID 7965CyclohexylamineHCID 178469580HCID 178469580, compound

Product 1

HCID 178433899HCID 178433899, compoundYield 10%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 7237O-XyleneSolvent

Procedure

A mixed solution of ethyl 4-hydroxy-3-methyl-1-(2-pyridinyl)-1H-pyrazolo[3,4-b]pyridine-5-carboxylate (1.5 g, 5.0 mmol) and cyclohexylamine (2.2 g, 22 mmol) in xylene (5.0 mL) and dimethylsulfoxide (5.0 mL) was stirred at 130° C. for 28 hours. The solution was cooled to room temperature and water was added thereto. Subsequently, organic matter was extracted with ethyl acetate. The extract was washed with saturated brine and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. Purification of the residue by silica gel column chromatography (chloroform:methanol=50:1 to 20:1) gave crude crystals. The crude crystals were recrystallized from ethyl acetate/ethanol to give the title compound (0.17 g, 10% yield).

Workup

  1. extractionSubsequently, organic matter was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customPurification of the residue by silica gel column chromatography (chloroform:methanol=50:1 to 20:1)
  6. customgave crude crystals
  7. customThe crude crystals were recrystallized from ethyl acetate/ethanol

Sources & evidence

ORD record
ord-141dd29ef21043eebb3bb0a343eb508d
Source dataset
uspto-grants-2005_09
Patent number
US06949648B2

Reaction notes

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