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

HRID 922850노트

반응식

HRID 922850 반응식
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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

실험 절차

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)+.

후처리

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

출처 및 근거

ORD 기록
ord-d7d0e35cf76f4f869f73e04358a77cd7
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09278961B2

반응 노트

불러오는 중…