4-Fluorobenzylamine → HCID 68952401, compound

HRID 1453833Notes

Reaction equation

HRID 1453833 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([C:21](OC)=[O:22])=[N:11][N:12]2[CH2:17][CH:16]([CH3:18])[N:15]([CH3:19])[C:14](=[O:20])[C:13]=12)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:25][C:26]1[CH:33]=[CH:32][C:29]([CH2:30][NH2:31])=[CH:28][CH:27]=1>CO>[CH2:1]([O:8][C:9]1[C:10]([C:21]([NH:31][CH2:30][C:29]2[CH:32]=[CH:33][C:26]([F:25])=[CH:27][CH:28]=2)=[O:22])=[N:11][N:12]2[CH2:17][CH:16]([CH3:18])[N:15]([CH3:19])[C:14](=[O:20])[C:13]=12)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 673264-FluorobenzylamineHCID 68953978HCID 68953978, compound

Product 1

HCID 68952401HCID 68952401, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 3-benzyloxy-5,6-dimethyl-4-oxo-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazine-2-carboxylate (72 mg, 0.219 mmol) in MeOH was added 4-fluorobenzylamine (376 μL, 3.28 mmol). The mixture was heated to reflux overnight and then at 110° C. for 4 hours. The mixture was purified by reverse phase chromatography on a C-18 column using a gradient elution of 95-5% H2O (0.1% TFA)/CH3CN (0.1% TFA), and collection and concentration of the appropriate fractions afforded the amide as a yellow oil. ES MS (M+1)=423.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux overnight
  3. customThe mixture was purified by reverse phase chromatography on a C-18 column
  4. washa gradient elution of 95-5% H2O (0.1% TFA)/CH3CN (0.1% TFA), and collection and concentration of the appropriate fractions

Sources & evidence

ORD record
ord-041bc1f0ac8c4cd5bc9cc50d5a62b099
Source dataset
uspto-grants-2009_01
Patent number
US07476666B2

Reaction notes

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