Morpholine → 4-(2,4-Dichloro-5-methoxyanilino)-7-methoxy-8-[2-(4-morpholinyl)ethoxy]benzo[b][1,8]naphthyridine-3-carbonitrile

HRID 2213840ノート

反応式

HRID 2213840 の反応式
Cl[CH2:2][CH2:3][O:4][C:5]1[C:6]([O:32][CH3:33])=[CH:7][C:8]2[C:9]([CH:31]=1)=[N:10][C:11]1[N:12]=[CH:13][C:14]([C:29]#[N:30])=[C:15]([NH:18][C:19]3[CH:24]=[C:23]([O:25][CH3:26])[C:22]([Cl:27])=[CH:21][C:20]=3[Cl:28])[C:16]=1[CH:17]=2.[I].[Na].[NH:36]1[CH2:41][CH2:40][O:39][CH2:38][CH2:37]1>>[Cl:28][C:20]1[CH:21]=[C:22]([Cl:27])[C:23]([O:25][CH3:26])=[CH:24][C:19]=1[NH:18][C:15]1[C:16]2[CH:17]=[C:8]3[CH:7]=[C:6]([O:32][CH3:33])[C:5]([O:4][CH2:3][CH2:2][N:36]4[CH2:41][CH2:40][O:39][CH2:38][CH2:37]4)=[CH:31][C:9]3=[N:10][C:11]=2[N:12]=[CH:13][C:14]=1[C:29]#[N:30]

参加物

4

反応物 3

HCID 8083MorpholineHCID 101641738-(2-Chloroethoxy)-4-(2,4-dichloro-5-methoxyanilino)-7-methoxybenzo[b][1,8]naphthyridine-3-carbonitrileHCID 178506594HCID 178506594、化合物

生成物 1

HCID 101662684-(2,4-Dichloro-5-methoxyanilino)-7-methoxy-8-[2-(4-morpholinyl)ethoxy]benzo[b][1,8]naphthyridine-3-carbonitrile収率 47%

実験手順

A mixture of 8-(2-chloroethoxy)-4-(2,4-dichloro-5-methoxyanilino)-7-methoxybenzo[b][1,8]naphthyridine-3-carbonitrile (202 mg, 0.40 mmol) and sodium iodine (70 mg, 0.47 mmol) in 4 mL of morpholine is heated at reflux for 2 hours. The reaction mixture is concentrated in vacuo and partitioned between ethyl acetate and water. The organic layer is washed with saturated sodium bicarbonate, dried over magnesium sulfate, filtered and concentrated in vacuo. Ethyl acetate is added to the residue and the orange solid is collected by filtration to provide 105 mg (47%) of 4-(2,4-dichloro-5-methoxyanilino)-7-methoxy-8-[2-(4-morpholinyl)ethoxy]benzo[b][1,8]naphthyridine-3-carbonitrile, mp 242–244° C. dec. MS 553.8, 555.8 (M+H)+ Analysis for C27H25Cl2N5O4 Calcd: C, 58.49; H, 4.54; N, 12.63. Found: C, 58.41; H, 4.23; N, 12.48.

後処理

  1. temperatureis heated
  2. temperatureat reflux for 2 hours
  3. concentrationThe reaction mixture is concentrated in vacuo
  4. custompartitioned between ethyl acetate and water
  5. washThe organic layer is washed with saturated sodium bicarbonate
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. additionEthyl acetate is added to the residue
  10. filtrationthe orange solid is collected by filtration

出典と根拠

ORDレコード
ord-66742b13fa874fe18cec29c8e7a28c54
出典データセット
uspto-grants-2006_09
特許番号
US07105531B2

反応ノート

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