Potassium Iodide → 4-Ethoxy-7-[2-[1-(6-methylpyridazin-3-yl)-4-piperidyl]ethoxy]quinazoline

HRID 1171629노트

반응식

HRID 1171629 반응식
Cl[CH2:2][CH2:3][CH:4]1[CH2:9][CH2:8][N:7]([C:10]2[N:11]=[N:12][C:13]([CH3:16])=[CH:14][CH:15]=2)[CH2:6][CH2:5]1.[OH:17][C:18]1[CH:27]=[C:26]2[C:21]([C:22]([O:28][CH2:29][CH3:30])=[N:23][CH:24]=[N:25]2)=[CH:20][CH:19]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CN(C=O)C>[CH3:16][C:13]1[N:12]=[N:11][C:10]([N:7]2[CH2:8][CH2:9][CH:4]([CH2:3][CH2:2][O:17][C:18]3[CH:27]=[C:26]4[C:21]([C:22]([O:28][CH2:29][CH3:30])=[N:23][CH:24]=[N:25]4)=[CH:20][CH:19]=3)[CH2:5][CH2:6]2)=[CH:15][CH:14]=1

참가 물질

6

반응물 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 149892183-[4-(2-Chloroethyl)-1-piperidinyl]-6-methylpyridazineHCID 1358487477-Hydroxy-4-ethoxyquinazoline

생성물 1

HCID 5044704-Ethoxy-7-[2-[1-(6-methylpyridazin-3-yl)-4-piperidyl]ethoxy]quinazoline수율 18%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
90 °C

실험 절차

A mixture of 3-[4-(2-chloroethyl)-1-piperidinyl]-6-methylpyridazine (76 mg, 318 μmol), 7-hydroxy-4-ethoxyquinazoline (100 mg, 526 μmol), potassium carbonate (109 mg, 789 μmol) and potassium iodide (53 mg, 319 μmol) in DMF (5 mL) was heated at 90° C. overnight in an argon atmosphere. The mixture was concentrated, and the residue partitioned between ethyl acetate (100 mL), and water (20 mL). The organic phase was dried (MgSO4), filtered, concentrated and purified by column chromatography (silica), using gradient elution (ethyl acetate-methanol/EA). The combined fractions gave a white solid (22 mg, 18%). The 1H nmr data are recorded in Table 6 below.

후처리

  1. concentrationThe mixture was concentrated
  2. customthe residue partitioned between ethyl acetate (100 mL), and water (20 mL)
  3. dry with materialThe organic phase was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by column chromatography (silica)
  7. washelution (ethyl acetate-methanol/EA)

출처 및 근거

ORD 기록
ord-ff1e5661d70f45439e1cd8d12aacb19b
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07829705B2

반응 노트

불러오는 중…