Potassium Carbonate → 3-amino-1-[{4-(2,4-dimethylphenyl)piperazin-1-yl}propanoyl]-6-N-benzyl-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridin-7-one

HRID 390023Notes

Reaction equation

HRID 390023 reaction equation
[C:1](=[O:4])([O-])[O-].[K+].[K+].C(O[C:12]([N:14]1[C:18]2O[N:20]([CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH2:21][CH2:22][C:17]=2[C:16]([NH2:30])=[N:15]1)=[O:13])(C)(C)C.ClC[CH2:33][C:34]([N:36]1[CH2:41][CH2:40][N:39]([C:42]2[CH:47]=[CH:46][C:45]([CH3:48])=[CH:44][C:43]=2[CH3:49])[CH2:38][CH2:37]1)=O>C(#N)C>[NH2:30][C:16]1[C:17]2[CH2:22][CH2:21][N:20]([CH2:23][C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)[C:1](=[O:4])[C:18]=2[N:14]([C:12](=[O:13])[CH2:33][CH2:34][N:36]2[CH2:41][CH2:40][N:39]([C:42]3[CH:47]=[CH:46][C:45]([CH3:48])=[CH:44][C:43]=3[CH3:49])[CH2:38][CH2:37]2)[N:15]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 679970803-Chloro-1-{4-(2,4-dimethylphenyl)piperazin-1-yl}propan-1-oneHCID 67997531t-Butyl-3-amino-6-benzyl-4,5,6,7-tetrahydro-7-oxapyrazolo[3,4-c]pyridin-1-carboxylate

Product 1

HCID 679970053-amino-1-[{4-(2,4-dimethylphenyl)piperazin-1-yl}propanoyl]-6-N-benzyl-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridin-7-oneYield 11.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Potassium carbonate (68.2 mg, 0.494 mmol) was added to a solution of t-butyl-3-amino-6-benzyl-4,5,6,7-tetrahydro-7-oxapyrazolo[3,4-c]pyridin-1-carboxylate (154 mg, 0.449 mmol) dissolved in anhydrous acetonitrile (1.9 mL) and then stirred at room temperature for 30 minutes. After adding 3-chloro-1-{4-(2,4-dimethylphenyl)piperazin-1-yl}propan-1-one (132.2 mg, 0.471 mmol), reaction was carried out overnight. A target compound (25.4 mg, 0.052 mmol, 11.6%) was yielded as white solid.

Workup

  1. additionAfter adding
  2. waitwas carried out overnight

Sources & evidence

ORD record
ord-53e1d2ac111147d79360de6a2da78ad2
Source dataset
uspto-grants-2013_02
Patent number
US08383631B2

Reaction notes

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