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

HRID 7482

반응식

HRID 7482 반응식
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

참가 물질

9

반응물 5

HCID 313Hydrochloric AcidHCID 4875Potassium IodideHCID 11430Potassium Carbonate2회HCID 958344-(3-Chloropropyl)morpholine2회HCID 1357525234-Chloro-7-hydroxy-6-methoxycinnoline

생성물 1

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

시약·촉매·용매 3

HCID 3776Isopropanol용매HCID 6228Dimethylformamide용매HCID 22242641Methanol--water (1/1)용매

반응 조건

온도
80 °C

실험 절차

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%).

후처리

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

출처 및 근거

ORD 기록
ord-245f2870f5024f29a93ebbc4e31b8a82
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07087602B2

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