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1,8-Diazabicyclo(5.4.0)undec-7-ene → ethyl 1-[2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethyl]-7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate

HRID 2364335
ノート
印刷プレビュー

反応式

HRID 2364335 の反応式
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH2:12][CH2:13][N:14]([C:34](=[O:41])[CH2:35][C:36]([O:38][CH2:39][CH3:40])=[O:37])[C:15]1[C:16]([C:29](OCC)=[O:30])=[N:17][CH:18]=[C:19]([CH2:21][C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=2)[CH:20]=1.C1CCN2C(=NCCC2)CC1.OS([O-])(=O)=O.[Na+]>CCO.O>[O:11]=[C:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[C:2](=[O:1])[N:3]1[CH2:12][CH2:13][N:14]1[C:15]2[C:16](=[N:17][CH:18]=[C:19]([CH2:21][C:22]3[CH:23]=[CH:24][C:25]([F:28])=[CH:26][CH:27]=3)[CH:20]=2)[C:29]([OH:30])=[C:35]([C:36]([O:38][CH2:39][CH3:40])=[O:37])[C:34]1=[O:41]
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 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 516919Sodium BisulfateHCID 69482077ethyl 3-{[2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethyl][3-(ethyloxy)-3-oxopropanoyl]amino}-5-[(4-fluorophenyl)methyl]-2-pyridinecarboxylate

生成物 1

HCID 69480967ethyl 1-[2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethyl]-7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒
HCID 962Water溶媒

実験手順

A solution of ethyl 3-{[2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethyl][3-(ethyloxy)-3-oxopropanoyl]amino}-5-[(4-fluorophenyl)methyl]-2-pyridinecarboxylate (2.05 g, 3.65 mmol) in EtOH (75 mL) under nitrogen was treated with DBU (0.709 mL, 4.74 mmol). After stirring at ambient temperature for 15 min., the reaction mixture was treated with 1N NaHSO4 (5.0 mL). The resulting slurry was diluted with water, filtered, the filtered solid was washed with water, EtOH, and Et2O and thoroughly dried under high vacuum to provide the title compound as a white solid: 1H NMR (400 MHz, CHLOROFORM-D) δ ppm 1.4 (t, J=7.0 Hz, 3 H), 4.0 (t, J=7.0 Hz, 4 H), 4.4 (t, J=6.5 Hz, 2 H), 4.5 (q, J=7.3 Hz, 2 H), 7.0 (t, J=8.5 Hz, 2 H), 7.1 (m, 2 H), 7.7 (dd, J=5.5, 3.1 Hz, 2 H), 7.8 (s, 1 H) 7.8 (m, 2 H), 8.4 (s, 1 H), 13.9 (none, 1 H); ES+ MS: 516 (M+H+).

後処理

  1. filtrationfiltered
  2. washthe filtered solid was washed with water, EtOH, and Et2O
  3. customthoroughly dried under high vacuum

出典と根拠

ORDレコード
ord-82979fae7ce04578a55ba35f99883e98
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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このページの内容参加物実験手順後処理出典と根拠反応ノート