Acetic Acid → 3-{5-[(2-Bicyclo[2.2.1]hept-2-ylethylamino)methyl]pyridin-2-yl}benzamide

HRID 561361Notes

Reaction equation

HRID 561361 reaction equation
[CH:1]([C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH:10]=[C:11]([CH:15]=[CH:16][CH:17]=2)[C:12]([NH2:14])=[O:13])=[N:7][CH:8]=1)=O.[CH:18]12[CH2:24][CH:21]([CH2:22][CH2:23]1)[CH2:20][CH:19]2[CH2:25][CH2:26][NH2:27].CC(O)=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl.CCOC(C)=O>[CH:18]12[CH2:24][CH:21]([CH2:22][CH2:23]1)[CH2:20][CH:19]2[CH2:25][CH2:26][NH:27][CH2:1][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH:10]=[C:11]([CH:15]=[CH:16][CH:17]=2)[C:12]([NH2:14])=[O:13])=[N:7][CH:8]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydrideHCID 202228702-{Bicyclo[2.2.1]heptan-2-yl}ethan-1-amineHCID 593165483-(5-Formylpyridin-2-yl)benzamide

Product 1

HCID 252169673-{5-[(2-Bicyclo[2.2.1]hept-2-ylethylamino)methyl]pyridin-2-yl}benzamide

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 3-(5-formylpyridin-2-yl)benzamide (Preparation 12, 108 mg, 0.48 mmol) in DCM (75 mL) was added 2-bicyclo[2.2.1]hept-2-ylethylamine (333 mg, 2.39 mmol), AcOH (80 μL, 1.4 mmol) and sodium triacetoxyborohydride (302 mg, 1.42 mmol). The mixture was stirred at rt for 16 h. EtOAc (100 mL) was added and the organic phase washed with aqueous NaHCO3 (30 mL), brine (30 mL) and dried (MgSO4). The solvent was removed in vacuo and the residue purified by column chromatography (10% MeOH: DCM to 20% MeOH: DCM) to give the title compound: RT=2.62 min; m/z (ES+)=350.0 [M+H]+.

Workup

  1. washthe organic phase washed with aqueous NaHCO3 (30 mL), brine (30 mL)
  2. dry with materialdried (MgSO4)
  3. customThe solvent was removed in vacuo
  4. customthe residue purified by column chromatography (10% MeOH: DCM to 20% MeOH: DCM)

Sources & evidence

ORD record
ord-5bffa0a0a6b34e92b11e5ed5a23a2aa3
Source dataset
uspto-grants-2011_11
Patent number
US08063247B2

Reaction notes

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