Ammonia → 6-[4-(1-cyano-1-methylethyl)phenyl]-1-(4-methoxyphenyl)-7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxamide

HRID 971144Notes

Reaction equation

HRID 971144 reaction equation
[C:1]([C:3]([CH3:34])([CH3:33])[C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][C:13]3[C:16]([C:27]([O:29]CC)=O)=[N:17][N:18]([C:19]4[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=4)[C:12]=3[C:11]2=[O:32])=[CH:6][CH:5]=1)#[N:2].[NH3:35]>C(O)CO>[C:1]([C:3]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][C:13]3[C:16]([C:27]([NH2:35])=[O:29])=[N:17][N:18]([C:19]4[CH:20]=[CH:21][C:22]([O:25][CH3:26])=[CH:23][CH:24]=4)[C:12]=3[C:11]2=[O:32])=[CH:6][CH:5]=1)([CH3:33])[CH3:34])#[N:2]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 59020140Ethyl 6-[4-(cyano-dimethyl-methyl)phenyl]-1-(4-methoxy-phenyl)-7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboylate

Product 1

HCID 590200716-[4-(1-cyano-1-methylethyl)phenyl]-1-(4-methoxyphenyl)-7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxamideYield 88%

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Conditions

Temperature
80 °C

Procedure

Ethyl 6-[4-(cyano-dimethyl-methyl)phenyl]-1-(4-methoxy-phenyl)-7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboylate (0.38 g, 0.83 mmol) obtained in Example 96 was placed in a sealed tube containing 10% ammonia in ethylene glycol (3 mL) and heated 80° C. for 2 h. The reaction was cooled, quenched with H2O, extracted with EtOAc, and dried (MgSO4). Recrystallization from CH2Cl2/Hexanes afforded 0.31 g (88%) of the title amide. High Resolution Mass Spec (M+H)+. for C24H24N5O3 430.1898.

Workup

  1. temperatureThe reaction was cooled
  2. customquenched with H2O
  3. extractionextracted with EtOAc
  4. dry with materialdried (MgSO4)
  5. customRecrystallization from CH2Cl2/Hexanes

Sources & evidence

ORD record
ord-2ca5de5cf55f41ac95693f38bde09b45
Source dataset
uspto-grants-2007_12
Patent number
US07312214B2

Reaction notes

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