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

HRID 1364627

반응식

HRID 1364627 반응식
NC[C:3]1[CH:24]=[CH:23][C:6]([C:7]([NH:9][C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[C:12]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=3)[CH:11]=2)=[O:8])=[CH:5][CH:4]=1.CC(O)=O.C=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[CH3:45][N:46]([CH:48]=O)[CH3:47]>>[Cl:16][C:13]1[CH:14]=[CH:15][C:10]([NH:9][C:7](=[O:8])[C:6]2[CH:5]=[CH:4][C:3]([CH2:48][N:46]([CH3:45])[CH3:47])=[CH:24][CH:23]=2)=[CH:11][C:12]=1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=1

참가 물질

6

반응물 5

HCID 176Acetic AcidHCID 712FormaldehydeHCID 6228DimethylformamideHCID 5049666Sodium triacetoxyborohydrideHCID 668779924-(aminomethyl)-N-(4-chloro-3-(pyridin-2-yl)phenyl)benzamide

생성물 1

HCID 58614907N-(4-chloro-3-(pyridin-2-yl)phenyl)-4-((dimethylamino)methyl)benzamide

실험 절차

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)+.

후처리

  1. concentrationThe reaction mixture was concentrated
  2. dissolutionthe crude residue was dissolved in ethyl acetate
  3. washwashed with 1 N sodium hydroxide
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customThe crude product was purified by reverse phase HPLC

출처 및 근거

ORD 기록
ord-5743bb444b73401fbcdc1b89fcc6d450
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07888364B2

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