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Dimethylamine → 4-methoxy-6-(4-methoxybenzyl)-N,N-dimethyl-5-oxo-5,6,7,8-tetrahydro-2,6-naphthyridine-1-carboxamide

HRID 1817344
ノート
印刷プレビュー

反応式

HRID 1817344 の反応式
[CH3:1][O:2][C:3]1[C:12]2[C:11](=[O:13])[N:10]([CH2:14][C:15]3[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=3)[CH2:9][CH2:8][C:7]=2[C:6]([C:23](O)=[O:24])=[N:5][CH:4]=1.C1[CH:31]=[N:30][C:29]2N(O)N=NC=2C=1.CNC>C1COCC1.C(Cl)CCl>[CH3:1][O:2][C:3]1[C:12]2[C:11](=[O:13])[N:10]([CH2:14][C:15]3[CH:16]=[CH:17][C:18]([O:21][CH3:22])=[CH:19][CH:20]=3)[CH2:9][CH2:8][C:7]=2[C:6]([C:23]([N:30]([CH3:31])[CH3:29])=[O:24])=[N:5][CH:4]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 674DimethylamineHCID 181649HOAtHCID 690648344-Methoxy-6-(4-methoxybenzyl)-5-oxo-5,6,7,8-tetrahydro-2,6-naphthyridine-1-carboxylic acid

生成物 1

HCID 690697114-methoxy-6-(4-methoxybenzyl)-N,N-dimethyl-5-oxo-5,6,7,8-tetrahydro-2,6-naphthyridine-1-carboxamide

試薬・触媒・溶媒 2

HCID 111,2-Dichloroethane溶媒
HCID 8028
Tetrahydrofuran
溶媒
2 回

実験手順

A 250 mL THF suspension of 4-methoxy-6-(4-methoxybenzyl)-5-oxo-5,6,7,8-tetrahydro-2,6-naphthyridine-1-carboxylic acid (11.0 g), 8.0 g EDC, 5.7 g HOAT, and 11.2 mL TEA was stirred at room temperature for 20 minutes, followed by addition of 45 mL of a 2M THF solution of dimethylamine and then stirring for 1.5 hours. The reaction was quenched with 200 mL of 1N aq HCl and stirred vigorously for 30 minutes. After concentrating in vacuo until an oil formed on the water layer, 200 mL chloroform was added. The water layer was washed again with chloroform then the combined organic layers were washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo to pure product by HPLC/MS and NMR.

後処理

  1. stirringstirring for 1.5 hours
  2. customThe reaction was quenched with 200 mL of 1N aq HCl
  3. stirringstirred vigorously for 30 minutes
  4. concentrationAfter concentrating in vacuo until an oil
  5. customformed on the water layer, 200 mL chloroform
  6. additionwas added
  7. washThe water layer was washed again with chloroform
  8. washthe combined organic layers were washed with brine
  9. dry with materialdried over sodium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo to pure product by HPLC/MS and NMR

出典と根拠

ORDレコード
ord-b1c82edb267f49a9ab68a899cff26038
出典データセット
uspto-grants-2009_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07598264B2

反応ノート

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