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

HRID 1268875

反応式

HRID 1268875 の反応式
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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
55 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-4a0ccd46beb140648fb87e5163786105
出典データセット
uspto-grants-2007_04
特許番号
US07199119B2

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