Trifluoroacetic acid → 1-(5-(3-(Aminomethyl)phenyl)-3,4-dihydroquinolin-1(2H)-yl)-4-(2,3-dimethylphenoxy)butan-1-one

HRID 2175248노트

반응식

HRID 2175248 반응식
[CH3:1][C:2]1[C:38]([CH3:39])=[CH:37][CH:36]=[CH:35][C:3]=1[O:4][CH2:5][CH2:6][CH2:7][C:8]([N:10]1[C:19]2[C:14](=[C:15]([C:20]3[CH:21]=[C:22]([CH:32]=[CH:33][CH:34]=3)[CH2:23][NH:24]C(=O)OC(C)(C)C)[CH:16]=[CH:17][CH:18]=2)[CH2:13][CH2:12][CH2:11]1)=[O:9].C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:24][CH2:23][C:22]1[CH:21]=[C:20]([C:15]2[CH:16]=[CH:17][CH:18]=[C:19]3[C:14]=2[CH2:13][CH2:12][CH2:11][N:10]3[C:8](=[O:9])[CH2:7][CH2:6][CH2:5][O:4][C:3]2[CH:35]=[CH:36][CH:37]=[C:38]([CH3:39])[C:2]=2[CH3:1])[CH:34]=[CH:33][CH:32]=1

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 70982891tert-Butyl 3-(1-(4-(2,3-dimethylphenoxy)butanoyl)-1,2,3,4-tetrahydroquinolin-5-yl)benzylcarbamate

생성물 1

HCID 709819111-(5-(3-(Aminomethyl)phenyl)-3,4-dihydroquinolin-1(2H)-yl)-4-(2,3-dimethylphenoxy)butan-1-one수율 77.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of tert-butyl 3-(1-(4-(2,3-dimethylphenoxy)butanoyl)-1,2,3,4-tetrahydroquinolin-5-yl)benzylcarbamate (0.12 g, 0.227 mmol) in DCM (2.5 mL) at 0° C. was added TFA (0.35 mL, 4.54 mmol) dropwise. The reaction mixture was slowly warmed to room temperature and stirred for 16 h. After this time, the reaction mixture was quenched with 50% saturated NaHCO3, and the aqueous phase was extracted with DCM. The combined organic layer was dried over anhydrous MgSO4, filtered, and concentrated in vacuo to afford the title compound (0.075 g, 77% yield). LCMS, [M+H]+=429.2.

후처리

  1. customAfter this time, the reaction mixture was quenched with 50% saturated NaHCO3
  2. extractionthe aqueous phase was extracted with DCM
  3. dry with materialThe combined organic layer was dried over anhydrous MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-b052780a5eac4b879db50aeceeac4a9a
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09062028B2

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