Dichloromethane → 4-methoxy-3-methyl-1-phenyl-6-(4-piperazin-1-yl-phenyl)-1H-pyrazolo[3,4-b]pyridine

HRID 68742Notes

Reaction equation

HRID 68742 reaction equation
[CH3:1][C:2]1[C:10]2[C:9](=[O:11])[CH:8]=[C:7]([C:12]3[CH:17]=[CH:16][C:15]([N:18]4[CH2:23][CH2:22][N:21](C(OC(C)(C)C)=O)[CH2:20][CH2:19]4)=[CH:14][CH:13]=3)[N:6](C)[C:5]=2[N:4]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[N:3]=1.Cl[CH2:39]Cl>FC(F)(F)C(O)=O>[CH3:39][O:11][C:9]1[CH:8]=[C:7]([C:12]2[CH:17]=[CH:16][C:15]([N:18]3[CH2:19][CH2:20][NH:21][CH2:22][CH2:23]3)=[CH:14][CH:13]=2)[N:6]=[C:5]2[N:4]([C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=3)[N:3]=[C:2]([CH3:1])[C:10]=12

Participants

4

Reactant 2

HCID 6344DichloromethaneHCID 67450400HCID 67450400, compound

Product 1

HCID 674477964-methoxy-3-methyl-1-phenyl-6-(4-piperazin-1-yl-phenyl)-1H-pyrazolo[3,4-b]pyridine

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Into a 50 mL round-bottom flask, was placed a solution of tert-butyl 4-(4-(3,7-dimethyl-4-oxo-1-phenyl-4,7-dihydro-1H-pyrazolo[3,4-b]pyridin-6-yl)phenyl)piperazine-1-carboxylate (270 mg, 0.54 mmol, 1.00 equiv) in dichloromethane (6 mL), trifluoroacetic acid (3 mL). The resulting solution was stirred overnight at room temperature. The resulting mixture was concentrated under vacuum. The pH value of the solution was adjusted to about 9-10 with sodium bicarbonate. The resulting solution was extracted with of ethyl acetate (3×10 mL), the organic layers combined and dried over anhydrous magnesium sulfate. The residue was applied onto a silica gel column with methanol:CH2Cl2 (1:30) to yield 4-methoxy-3-methyl-1-phenyl-6-(4-piperazin-1-yl-phenyl)-1H-pyrazolo[3,4-b]pyridine as a white solid.

Workup

  1. customInto a 50 mL round-bottom flask, was placed
  2. concentrationThe resulting mixture was concentrated under vacuum
  3. extractionThe resulting solution was extracted with of ethyl acetate (3×10 mL)
  4. dry with materialdried over anhydrous magnesium sulfate

Sources & evidence

ORD record
ord-f61de46a1e4f4c9287873db02b91010e
Source dataset
uspto-grants-2014_09
Patent number
US08822447B2

Reaction notes

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