Dichloromethane → 1-(4-Amino-2-phenyl-thieno[3,2-c]pyridin-7-yl)-ethanone

HRID 1268875

반응식

HRID 1268875 반응식
Cl[C:2]1[C:7]2[CH:8]=[C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[S:10][C:6]=2[C:5]([C:17](=[O:19])[CH3:18])=[CH:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+].COC1C=CC(C[NH2:33])=CC=1.ClCCl>CN(C=O)C.CO>[NH2:33][C:2]1[C:7]2[CH:8]=[C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[S:10][C:6]=2[C:5]([C:17](=[O:19])[CH3:18])=[CH:4][N:3]=1

참가 물질

7

반응물 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 754524-MethoxybenzylamineHCID 184465121-(4-Chloro-2-phenyl-thieno[3,2-c]pyridin-7-yl)-ethanone

생성물 1

HCID 102650281-(4-Amino-2-phenyl-thieno[3,2-c]pyridin-7-yl)-ethanone

시약·촉매·용매 2

HCID 887Methanol용매HCID 6228Dimethylformamide용매

반응 조건

온도
55 °C

실험 절차

To a suspension of 1-(4-chloro-2-phenyl-thieno[3,2-c]pyridin-7-yl)-ethanone 97 (61 mg, 0.21 mmol) and potassium carbonate (174 mg, 1.26 mmol) in DMF (1.8 mL) was added 4-methoxybenzylamine (85 μl, 0.64 mmol). The resultant mixture was heated at 50° C. for 6.75 h. After this time, 20 mL of a 1:1 mixture of dichloromethane and methanol was added and the resultant slurry was filtered. The filtrate was concentrated and the residue was dissolved in trifluoroacetic acid (7 mL). The resultant mixture was heated at 55° C. for 2.75 h. After this time, the reaction mixture was concentrated and the residue was purified by silica gel column chromatography (eluent: dichloromethane:MeOH:Et3N, 98.5:1.5:0.5) to give 98. 1H NMR (400 MHz, CDCl3) δ: 2.66 (s, 3H), 5.78–6.15 (br s, 2H), 7.37 (t, J=7.0 Hz, 1H), 7.45 (t, J=7.5 Hz, 2H), 7.54 (s, 1H), 8.0 (d, J=3.5 Hz, 2H), 8.56 (s, 1H). MS (EI) m/z (M+H+) 269.

후처리

  1. additionwas added
  2. filtrationthe resultant slurry was filtered
  3. concentrationThe filtrate was concentrated
  4. dissolutionthe residue was dissolved in trifluoroacetic acid (7 mL)
  5. concentrationAfter this time, the reaction mixture was concentrated
  6. customthe residue was purified by silica gel column chromatography (eluent: dichloromethane:MeOH:Et3N, 98.5:1.5:0.5)

출처 및 근거

ORD 기록
ord-4a0ccd46beb140648fb87e5163786105
출처 데이터셋
uspto-grants-2007_04
특허 번호
US07199119B2

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