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

HRID 624103ノート

反応式

HRID 624103 の反応式
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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
90 °C

実験手順

A mixture of 3-[4-(2-chloroethyl)-1-piperidinyl]-6-methylpyridazine (76 mg, 318 μmol), 7-hydroxy-4-ethoxyquinazoline (100 mg, 526 mmol), potassium carbonate (109 mg, 789 mmol) and potassium iodide (53 mg, 319 mmol) 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.

後処理

  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)

出典と根拠

ORDレコード
ord-2df3f614c09b44bbb766e9594385b2f0
出典データセット
uspto-grants-2016_04
特許番号
US09303026B2

反応ノート

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