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Acetic Anhydride → 1-[2-(Acetylamino)ethyl]-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-{2-[(1-methylethyl)oxy]ethyl}-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide

HRID 2364385
ノート
印刷プレビュー

反応式

HRID 2364385 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][O:28][CH:29]([CH3:31])[CH3:30])=[O:24])[C:5]1=[O:32].C(N(C(C)C)CC)(C)C.[C:42](OC(=O)C)(=[O:44])[CH3:43]>CN(C=O)C>[C:42]([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][O:28][CH:29]([CH3:30])[CH3:31])=[O:24])[C:5]1=[O:32])(=[O:44])[CH3:43]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 7918Acetic AnhydrideHCID 81531DiisopropylethylamineHCID 694825271-(2-Aminoethyl)-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-{2-[(1-methylethyl)oxy]ethyl}-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide

生成物 1

HCID 694830761-[2-(Acetylamino)ethyl]-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-{2-[(1-methylethyl)oxy]ethyl}-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide

試薬・触媒・溶媒 1

HCID 6228
Dimethylformamide
溶媒

実験手順

A solution of 1-(2-aminoethyl)-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-{2-[(1-methylethyl)oxy]ethyl}-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide (0.021 g, 0.046 mmol) and diisopropyl ethylamine (0.04 mL, 0.23 mmol) in DMF (5 mL) under nitrogen was treated with acetic anhydride (0.0046 mL, 0.048 mmol) at ambient temperature. The reaction was concentrated in vacuo and the resulting residue was treated with 1 N NaHSO4. Extracted the mixture twice with EtOAc, combined the organics, dried over MgSO4, filtered and concentrated the filtrate. The residue was then triturated with Et2O, filtered, and dried in vacuo to provide the title compound as an off-white solid: 1H NMR (300 MHz, DMSO-D6) δ ppm 1.1 (d, J=6.0 Hz, 6 H), 1.7 (s, 3 H), 3.3 (q, J=6.1, 2 H), 3.5 (m, 3 H), 3.6 (m, 2 H), 4.1 (s, 2 H), 4.3 (t, J=6.5 Hz, 2 H), 7.1 (m, 2 H), 7.4 (ddd, J=12.1, 5.5, 3.2 Hz, 2 H), 8.0 (d, J=6.0 Hz, 1 H), 8.2 (d, J=1.3 Hz, 1 H), 8.5 (d, J=1.5 Hz, 1 H), 10.4 (t, J=5.1 Hz, 1 H), 17.1 (s, 1 H); ES+ MS: 485 (M+H+).

後処理

  1. concentrationThe reaction was concentrated in vacuo
  2. additionthe resulting residue was treated with 1 N NaHSO4
  3. extractionExtracted the mixture twice with EtOAc
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated the filtrate
  7. customThe residue was then triturated with Et2O
  8. filtrationfiltered
  9. customdried in vacuo

出典と根拠

ORDレコード
ord-46de8482f37b4422877b1144be8c7ad9
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

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