Pyridine → HCID 18925013、化合物

HRID 1869082ノート

反応式

HRID 1869082 の反応式
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:17][CH2:18][CH2:19][O:20][CH3:21])=[C:9]([O:12][CH2:13][CH2:14][O:15][CH3:16])[CH:10]=2)[N:5]=[CH:4][N:3]=1.N1C=CC=CC=1.[C:28]([C:30]1[CH:31]=[C:32]([C:34]([CH3:37])=[CH:35][CH:36]=1)[NH2:33])#[CH:29]>CN(C=O)C>[ClH:1].[CH3:16][O:15][CH2:14][CH2:13][O:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][C:8]=1[O:17][CH2:18][CH2:19][O:20][CH3:21])[N:5]=[CH:4][N:3]=[C:2]2[NH:33][C:32]1[CH:31]=[C:30]([C:28]#[CH:29])[CH:36]=[CH:35][C:34]=1[CH3:37]

参加物

5

反応物 3

HCID 1049PyridineHCID 112899424-Chloro-6,7-bis(2-methoxyethoxy)quinazolineHCID 189250605-Ethynyl-2-methylaniline

生成物 1

HCID 18925013HCID 18925013、化合物収率 19%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

4-Chloro-6,7-bis-(2-methoxy-ethoxy)-quinazoline (153 mg, 0.49 mmol), pyridine (40 μL) and 3-ethynyl-6-methylaniline (71 mg, 0.54 mmol) were reacted in DMF (3 mL) at 110° C. under an atmosphere of N2 for 36 hours. The solvent was removed in vacuo and the residue was partitioned between CHCl3 and saturated aqueous NaHCO3. The organic extracts were washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The crude product was chromatographed on silica using 40% acetone/CH2Cl2 to provide 40 mg (19%) of pure product as its free base. This oil was dissolved in a minimum volume of CHCl3, diluted with several volumes of ether, and triturated with 1M HCl in ether to precipitate the title product as a white solid (M.P. 170°-185° C. (dec); LC-MS: 408 (MH+); anal. RP18-HPLC RT: 3.93 min.).

後処理

  1. customThe solvent was removed in vacuo
  2. customthe residue was partitioned between CHCl3 and saturated aqueous NaHCO3
  3. washThe organic extracts were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was chromatographed on silica using 40% acetone/CH2Cl2

出典と根拠

ORDレコード
ord-8018fffc136b4a88a48ffd6b2c0b0e07
出典データセット
uspto-grants-2009_12
特許番号
USRE041065E1

反応ノート

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