5-Amino-3-methyl-1-phenyl-1H-pyrazole-4-carboxamide → HCID 135985433, compound

HRID 68724Notes

Reaction equation

HRID 68724 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:5]=[C:4]([CH3:13])[C:3]=1[C:14]([NH2:16])=[O:15].[N:17]1[CH:22]=[CH:21][CH:20]=[C:19]([N:23]2[CH2:28][CH2:27][CH:26]([C:29](OCC)=O)[CH2:25][CH2:24]2)[CH:18]=1>C(O)C>[CH3:13][C:4]1[C:3]2[C:14](=[O:15])[NH:16][C:29]([CH:26]3[CH2:25][CH2:24][N:23]([C:19]4[CH:18]=[N:17][CH:22]=[CH:21][CH:20]=4)[CH2:28][CH2:27]3)=[N:1][C:2]=2[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:5]=1

Participants

4

Reactant 2

HCID 158367655-Amino-3-methyl-1-phenyl-1H-pyrazole-4-carboxamideHCID 67448378Ethyl 1-(pyridin-3-yl)piperidine-4-carboxylate

Product 1

HCID 135985433HCID 135985433, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Into a 100-mL 3-necked round-bottom flask, was placed a solution of Na (64 mg, 2.78 mmol, 6.00 equiv) in ethanol (5 mL) at room temperature. To the resulting mixture was then added a solution of 5-amino-3-methyl-1-phenyl-1H-pyrazole-4-carboxamide (100 mg, 0.46 mmol, 1.00 equiv) in C4H10O (10 mL), in portions at room temperature, followed by a solution of ethyl 1-(pyridin-3-yl)piperidine-4-carboxylate (650 mg, 2.78 mmol, 6.00 equiv) in C4H10O (20 mL), in portions at room temperature. The resulting solution was heated to reflux for 5 hr. The reaction was then quenched by the addition of water (10 mL). The resulting solution was extracted with DCM (3×30 mL) and the organic layers combined. The resulting mixture was washed with sodium chloride (2×50 mL), then dried over anhydrous sodium sulfate. The solids were filtered out. The resulting mixture was concentrated under vacuum. The residue was applied onto a silica gel column with dichloromethane/methanol (50:1) to yield 3-methyl-1-phenyl-6-(1-(pyridin-3-yl)piperidin-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-4(5H)-one as a white solid.

Workup

  1. customInto a 100-mL 3-necked round-bottom flask, was placed
  2. customat room temperature
  3. customat room temperature
  4. temperatureThe resulting solution was heated
  5. temperatureto reflux for 5 hr
  6. customThe reaction was then quenched by the addition of water (10 mL)
  7. extractionThe resulting solution was extracted with DCM (3×30 mL)
  8. washThe resulting mixture was washed with sodium chloride (2×50 mL)
  9. dry with materialdried over anhydrous sodium sulfate
  10. filtrationThe solids were filtered out
  11. concentrationThe resulting mixture was concentrated under vacuum

Sources & evidence

ORD record
ord-d1bd2881ad714066b1b1a0e41f5781c4
Source dataset
uspto-grants-2014_09
Patent number
US08822447B2

Reaction notes

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