Acetic Acid → 2-chloro-N-(4-chloro-3-(pyridin-2-yl)phenyl)-4-((dimethylamino)methyl)benzamide

HRID 922839Notes

Reaction equation

HRID 922839 reaction equation
[Cl:1][C:2]1[CH:23]=[C:22](CN)[CH:21]=[CH:20][C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[C:9]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=2)[CH:8]=1)=[O:5].CC(O)=O.C=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[CH3:46][N:47]([CH:49]=O)[CH3:48]>>[Cl:1][C:2]1[CH:23]=[C:22]([CH2:49][N:47]([CH3:46])[CH3:48])[CH:21]=[CH:20][C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[C:9]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=2)[CH:8]=1)=[O:5]

Participants

6

Reactant 5

HCID 176Acetic AcidHCID 712FormaldehydeHCID 6228DimethylformamideHCID 5049666Sodium triacetoxyborohydrideHCID 668770292-chloro-N-(4-chloro-3-(pyridin-2-yl)phenyl)-4-(aminomethyl)benzamide

Product 1

HCID 442521482-chloro-N-(4-chloro-3-(pyridin-2-yl)phenyl)-4-((dimethylamino)methyl)benzamide

Procedure

2-chloro-N-(4-chloro-3-(pyridin-2-yl)phenyl)-4-(aminomethyl)benzamide (80 mg, 0.20 mmol) was dissolved in DMF (5 mL) and treated with AcOH (10 uL), paraformaldehyde (43 mg, 0.47 mmol), and sodium triacetoxyborohydride (125 mg, 0.59 mmol). After stirring for 16 h, the solvent was evaporated and the residue was dissolved in ethyl acetate. The organic layer was washed with 1 N Sodium hydroxide, dried (MgSO4) and concentrated. The crude product was purified by reverse phase HPLC to produce 2-chloro-N-(4-chloro-3-(pyridin-2-yl)phenyl)-4-((dimethylamino)methyl)benzamide. MS (Q1) 400.0 (M)+.

Workup

  1. customthe solvent was evaporated
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washThe organic layer was washed with 1 N Sodium hydroxide
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customThe crude product was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-c4b76dd4dc604b138e4dfdb6960950b1
Source dataset
uspto-grants-2016_03
Patent number
US09278961B2

Reaction notes

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