Hydrochloric Acid → 4-Chloro-6-methoxy-7-(3-morpholinopropoxy)cinnoline

HRID 7482

反応式

HRID 7482 の反応式
Cl[CH2:2][CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1.[Cl:11][C:12]1[C:21]2[C:16](=[CH:17][C:18]([OH:24])=[C:19]([O:22][CH3:23])[CH:20]=2)[N:15]=[N:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+].Cl>CN(C=O)C.C(O)(C)C.O.CO>[Cl:11][C:12]1[C:21]2[C:16](=[CH:17][C:18]([O:24][CH2:2][CH2:3][CH2:4][N:5]3[CH2:10][CH2:9][O:8][CH2:7][CH2:6]3)=[C:19]([O:22][CH3:23])[CH:20]=2)[N:15]=[N:14][CH:13]=1

参加物

9

反応物 5

HCID 313Hydrochloric AcidHCID 4875Potassium IodideHCID 11430Potassium Carbonate2 回HCID 958344-(3-Chloropropyl)morpholine2 回HCID 1357525234-Chloro-7-hydroxy-6-methoxycinnoline

生成物 1

HCID 219910594-Chloro-6-methoxy-7-(3-morpholinopropoxy)cinnoline

試薬・触媒・溶媒 3

HCID 3776Isopropanol溶媒HCID 6228Dimethylformamide溶媒HCID 22242641Methanol--water (1/1)溶媒

反応条件

温度
80 °C

実験手順

The starting material 4-chloro-6-methoxy-7-(3-morpholinopropoxy)cinnoline hydrochloride was obtained by adding 1-chloro-3-morpholinopropane (190 mg, 0.95 mmol), (prepared as described in U.S. Pat. No. 4,004,007), to a suspension of 4-chloro-7-hydroxy-6-methoxycinnoline (0.2 g, 0.95 mmol), (prepared as described for the starting material in Example 10), in DMF (5 ml) containing potassium carbonate (327 mg, 2.3 mmol) and potassium iodide (15 mg, 0.095 mmol). After heating at 80° C. for 2 hours, potassium carbonate (65 mg, 0.47 mmol) and more 1-chloro-3-morpholinopropane (95 mg, 0.47 mmol) were added. After stirring for 4 hours at 80° C. the reaction mixture was cooled and 7M hydrogen chloride in isopropanol (407 μl) was added. The solution was poured onto a Diaion (trade mark of Mitsubishi) HP20SS column, using water/methanol (100/0 to 0/100 as a gradient) to give 4-chloro-6-methoxy-7-(3-morpholinopropoxy)cinnoline as an hydrochloride salt (175 mg, 44%).

後処理

  1. custom(prepared
  2. custom(prepared
  3. temperaturewas cooled
  4. additionThe solution was poured onto a Diaion (trade mark of Mitsubishi) HP20SS column

出典と根拠

ORDレコード
ord-245f2870f5024f29a93ebbc4e31b8a82
出典データセット
uspto-grants-2006_08
特許番号
US07087602B2

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