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Water → 1-[2-(Acetylamino)ethyl]-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-(2-hydroxyethyl)-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide

HRID 2364337
ノート
印刷プレビュー

反応式

HRID 2364337 の反応式
[NH2:1][CH2:2][CH2:3][N:4]1[C:13]2[C:8](=[N:9][CH:10]=[C:11]([CH2:14][C:15]3[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=3)[CH:12]=2)[C:7]([OH:22])=[C:6]([C:23]([NH:25][CH2:26][CH2:27][OH:28])=[O:24])[C:5]1=[O:29].C(N(C(C)C)CC)(C)C.[C:39](OC(=O)C)(=[O:41])[CH3:40].O>CN(C=O)C>[C:39]([NH:1][CH2:2][CH2:3][N:4]1[C:13]2[C:8](=[N:9][CH:10]=[C:11]([CH2:14][C:15]3[CH:16]=[CH:17][C:18]([F:21])=[CH:19][CH:20]=3)[CH:12]=2)[C:7]([OH:22])=[C:6]([C:23]([NH:25][CH2:26][CH2:27][OH:28])=[O:24])[C:5]1=[O:29])(=[O:41])[CH3:40]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 962WaterHCID 7918Acetic AnhydrideHCID 81531DiisopropylethylamineHCID 694804131-(2-Aminoethyl)-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-(2-hydroxyethyl)-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide

生成物 1

HCID 694801751-[2-(Acetylamino)ethyl]-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-(2-hydroxyethyl)-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide

試薬・触媒・溶媒

1
HCID 6228Dimethylformamide溶媒

反応条件

温度
0 °C

実験手順

A solution of 1-(2-aminoethyl)-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-(2-hydroxyethyl)-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide (0.019 g, 0.047 mmol) and diisopropyl ethylamine (0.075 mL, 0.43 mmol) in DMF (1 mL) under nitrogen was treated with acetic anhydride (0.004 mL, 0.042 mmol) at ambient temperature. The reaction was warmed slightly to solubilize then reacted at ambient temperature for 10 min. Water was added (2 mL) and the reaction was cooled to 0° C. and concentrated in vacuo. The resulting residue was treated with 1 N NaHSO4 and filtered then triturated with Et2O and dried in air to provide the title compound as an off-white solid: 1H NMR (300 MHz, DMSO-D6) δ ppm 1.7 (s, 3 H), 3.3 (dd, J=3.1, 1.3 Hz, 2 H), 3.4 (m, 2 H), 3.6 (m, 2 H), 4.1 (s, 2 H), 4.3 (m, 2 H), 4.9 (t, J=4.8 Hz, 1 H), 7.1 (t, J=8.8 Hz, 2 H), 7.4 (m, 2 H), 8.0 (m, 1 H), 8.2 (s, 1 H), 8.5 (s, 1 H), 10.4 (d, J=6.2 Hz, 1 H), 17.2 (s, 1 H); ES+ MS: 443 (M+H+).

後処理

  1. temperatureThe reaction was warmed slightly
  2. customto solubilize then reacted at ambient temperature for 10 min
  3. concentrationconcentrated in vacuo
  4. additionThe resulting residue was treated with 1 N NaHSO4
  5. filtrationfiltered
  6. customthen triturated with Et2O
  7. customdried in air

出典と根拠

ORDレコード
ord-db9c537fa59b4be0b497b7198e22362a
出典データセット
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08691991B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート