5-Amino-3-methyl-1-phenyl-1H-pyrazole-4-carboxamide → tert-butyl 3-(3-(3-methyl-4-oxo-1-phenyl-4,5-dihydro-1H-pyrazolo[3,4-d]pyrimidin-6-yl)piperidin-1-yl)azetidine-1-carboxylate

HRID 68725

Reaction equation

HRID 68725 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].[C:17]([O:21][C:22]([N:24]1[CH2:27][CH:26]([N:28]2[CH2:33][CH2:32][CH2:31][CH:30]([C:34](OC)=O)[CH2:29]2)[CH2:25]1)=[O:23])([CH3:20])([CH3:19])[CH3:18]>C(O)C>[CH3:13][C:4]1[C:3]2[C:14](=[O:15])[NH:16][C:34]([CH:30]3[CH2:31][CH2:32][CH2:33][N:28]([CH:26]4[CH2:25][N:24]([C:22]([O:21][C:17]([CH3:18])([CH3:20])[CH3:19])=[O:23])[CH2:27]4)[CH2:29]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 67448521HCID 67448521, compound

Product 1

HCID 136386278tert-butyl 3-(3-(3-methyl-4-oxo-1-phenyl-4,5-dihydro-1H-pyrazolo[3,4-d]pyrimidin-6-yl)piperidin-1-yl)azetidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Into a 100-mL 3-necked round-bottom flask, was placed a solution of Na (128 mg, 5.57 mmol, 6.00 equiv) in ethanol (10 mL) at room temperature. To the resulting mixture was then added a solution of 5-amino-3-methyl-1-phenyl-1H-pyrazole-4-carboxamide (200 mg, 0.93 mmol, 1.00 equiv) in C4H10O (10 mL), in portions at room temperature, followed by a solution of methyl 1-(1-(tert-butoxycarbonyl)azetidin-3-yl)piperidine-3-carboxylate (1.66 g, 5.57 mmol, 6.00 equiv) in C4H10O (20 mL), in portions at room temperature. The resulting solution was heated to reflux overnight. The reaction was then quenched by the addition of water (20 mL). The resulting solution was extracted with DCM (3×30 mL) and the organic layers combined. The resulting mixture was washed with sodium chloride (2×30 mL). The mixture was 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 tert-butyl 3-(3-(3-methyl-4-oxo-1-phenyl-4,5-dihydro-1H-pyrazolo[3,4-d]pyrimidin-6-yl)piperidin-1-yl)azetidine-1-carboxylate as a yellow 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 overnight
  6. customThe reaction was then quenched by the addition of water (20 mL)
  7. extractionThe resulting solution was extracted with DCM (3×30 mL)
  8. washThe resulting mixture was washed with sodium chloride (2×30 mL)
  9. dry with materialThe mixture was dried over anhydrous sodium sulfate
  10. filtrationthe solids were filtered out
  11. concentrationThe resulting mixture was concentrated under vacuum

Sources & evidence

ORD record
ord-18d67e092e0a427099d380a283d7c933
Source dataset
uspto-grants-2014_09
Patent number
US08822447B2

Linked notes

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