Trifluoroacetic acid → 4-(aminomethyl)-N-(4-chloro-3-(pyridin-2-yl)phenyl)benzamide

HRID 922850Notes

Reaction equation

HRID 922850 reaction equation
C([C:8]1[CH:16]=[C:15]([CH2:17][NH2:18])[CH:14]=[CH:13][C:9]=1[C:10]([OH:12])=O)(OC(C)(C)C)=O.[Cl:19][C:20]1[CH:26]=[CH:25][C:23]([NH2:24])=[CH:22][C:21]=1[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=1.C(O)(C(F)(F)F)=O>O>[NH2:18][CH2:17][C:15]1[CH:16]=[CH:8][C:9]([C:10]([NH:24][C:23]2[CH:25]=[CH:26][C:20]([Cl:19])=[C:21]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=3)[CH:22]=2)=[O:12])=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 401519254-Chloro-3-(pyridin-2-yl)anilineHCID 66878017BOC-4-(aminomethyl)benzoic acid

Product 1

HCID 668779924-(aminomethyl)-N-(4-chloro-3-(pyridin-2-yl)phenyl)benzamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Procedure G was used to couple BOC-4-(aminomethyl)benzoic acid (48 mg) with 4-chloro-3-(pyridin-2-yl)aniline (35 mg). The crude reaction mixture was treated with TFA (1 mL) containing trace amounts of water for 1 h. The reaction mixture was concentrated to yield 4-(aminomethyl)-N-(4-chloro-3-(pyridin-2-yl)phenyl)benzamide. 4-(aminomethyl)-N-(4-chloro-3-(pyridin-2-yl)phenyl)benzamide (80 mg) was dissolved in DMF (5 mL) and treated with AcOH (10 L), paraformaldehyde (48 mg), and sodium triacetoxyborohydride (125 mg) for 16 h. The reaction mixture was concentrated, and the crude residue was dissolved in ethyl acetate and washed with 1 N sodium hydroxide, dried (MgSO4) and concentrated. The crude product was purified by reverse phase HPLC to yield N-(4-chloro-3-(pyridin-2-yl)phenyl)-4-((dimethylamino)methyl)benzamide. MS (Q1) 365.0 (M)+.

Workup

  1. customThe crude reaction mixture
  2. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-d7d0e35cf76f4f869f73e04358a77cd7
Source dataset
uspto-grants-2016_03
Patent number
US09278961B2

Reaction notes

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