4-Fluorobenzylamine → 3-cyano-N-[(4-fluorophenyl)methyl]-6-hydroxy-7-oxo-1H-pyrazolo[1,5-a]pyrimidine-5-carboxamide;(4-fluorophenyl)methanamine

HRID 536117Notes

Reaction equation

HRID 536117 reaction equation
CO[C:3]([C:5]1[N:6]=[C:7]2[C:15]([C:16]#[N:17])=[CH:14][NH:13][N:8]2[C:9](=[O:12])[C:10]=1[OH:11])=[O:4].[F:18][C:19]1[CH:26]=[CH:25][C:22]([CH2:23][NH2:24])=[CH:21][CH:20]=1>CO>[F:18][C:19]1[CH:26]=[CH:25][C:22]([CH2:23][NH2:24])=[CH:21][CH:20]=1.[F:18][C:19]1[CH:26]=[CH:25][C:22]([CH2:23][NH:24][C:3]([C:5]2[N:6]=[C:7]3[C:15]([C:16]#[N:17])=[CH:14][NH:13][N:8]3[C:9](=[O:12])[C:10]=2[OH:11])=[O:4])=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 673264-FluorobenzylamineHCID 574945263-Cyano-6-hydroxy-7-oxo-1,7-dihydro-pyrazolo[1,5-a]pyrimidine-5-carboxylic acid methyl ester

Product 1

HCID 866430543-cyano-N-[(4-fluorophenyl)methyl]-6-hydroxy-7-oxo-1H-pyrazolo[1,5-a]pyrimidine-5-carboxamide;(4-fluorophenyl)methanamineYield 18%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-Cyano-6-hydroxy-7-oxo-1,7-dihydro-pyrazolo[1,5-a]pyrimidine-5-carboxylic acid methyl ester (100 mg, 0.427 mmol) was suspended in MeOH (10 mL) and to this was added 4-fluorobenzylamine (122 μL, 1.07 mmol) and the reaction was heated at reflux for 2 days before being cooled to room temperature and filtered. The filtrate was concentrated and recrystalised from hot methanol to afford the product a yellow solid (25 mg, 18%).

Workup

  1. temperaturethe reaction was heated
  2. temperatureat reflux for 2 days
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated
  5. customrecrystalised from hot methanol

Sources & evidence

ORD record
ord-1acf7a95b27b46b19945d26adf0fb889
Source dataset
uspto-grants-2014_10
Patent number
US08859563B2

Reaction notes

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