4-Fluorobenzylamine → HCID 59392856, compound

HRID 536141Notes

Reaction equation

HRID 536141 reaction equation
C[O:2][C:3]([C:5]1[N:6]=[C:7]2[C:15]3[C:14]([N:16]4[CH2:21][CH2:20][O:19][CH2:18][CH2:17]4)=[CH:13][CH:12]=[CH:11][C:10]=3[NH:9][N:8]2[C:22](=[O:25])[C:23]=1[OH:24])=O.C[O-].[Na+].[F:29][C:30]1[CH:37]=[CH:36][C:33]([CH2:34][NH2:35])=[CH:32][CH:31]=1>CO>[F:29][C:30]1[CH:37]=[CH:36][C:33]([CH2:34][NH:35][C:3]([C:5]2[N:6]=[C:7]3[C:15]4[C:14]([N:16]5[CH2:17][CH2:18][O:19][CH2:20][CH2:21]5)=[CH:13][CH:12]=[CH:11][C:10]=4[NH:9][N:8]3[C:22](=[O:25])[C:23]=2[OH:24])=[O:2])=[CH:32][CH:31]=1

Participants

5

Reactant 3

HCID 673264-FluorobenzylamineHCID 10942334Sodium MethoxideHCID 59392871HCID 59392871, compound

Product 1

HCID 59392856HCID 59392856, compoundYield 38.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The product from Example 21.2 (172 mg, 0.5 mmol), sodium methoxide (54 mg, 1.0 mmol) and 4-fluoro benzylamine (1.87 mg, 1.5 mmol) in methanol (15 mL) were combined and heated with stirring at reflux overnight. The mixture was cooled to room temperature and the resulting solid was collected by filtration and dissolved in dichloromethane (30 mL). The solution was washed with aqueous hydrochloric acid (2.0 M), water, dried and concentrated in vacuo to afford desired compound (84 mg, 38.4).

Workup

  1. temperatureheated
  2. temperatureat reflux overnight
  3. filtrationthe resulting solid was collected by filtration
  4. dissolutiondissolved in dichloromethane (30 mL)
  5. washThe solution was washed with aqueous hydrochloric acid (2.0 M), water
  6. customdried
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f7898a56e40743258a80e45fa1400312
Source dataset
uspto-grants-2014_10
Patent number
US08859563B2

Reaction notes

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