Ethoxyethylamine → 1-[2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethyl]-N-[2-(ethyloxy)ethyl]-7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide

HRID 2364336ノート

反応式

HRID 2364336 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]1[C:23]2[C:18](=[N:19][CH:20]=[C:21]([CH2:24][C:25]3[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=3)[CH:22]=2)[C:17]([OH:32])=[C:16]([C:33](OCC)=[O:34])[C:15]1=[O:38].[CH2:39]([O:41][CH2:42][CH2:43][NH2:44])[CH3:40]>CCO>[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:23]2[C:18](=[N:19][CH:20]=[C:21]([CH2:24][C:25]3[CH:26]=[CH:27][C:28]([F:31])=[CH:29][CH:30]=3)[CH:22]=2)[C:17]([OH:32])=[C:16]([C:33]([NH:44][CH2:43][CH2:42][O:41][CH2:39][CH3:40])=[O:34])[C:15]1=[O:38]

参加物

4

反応物 2

HCID 66970EthoxyethylamineHCID 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

生成物 1

HCID 694828111-[2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethyl]-N-[2-(ethyloxy)ethyl]-7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A solution of 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 (0.021 g, 0.041 mmol) in EtOH (2 mL) under nitrogen was treated with Ethoxyethylamine (0.021 mL, 0.2 mmol) for 10 min.@150° C. in a microwave vessel then@180° C. for an additional 10 min. After the reaction was cooled to ambient temperature the resulting suspension was filtered, and the filtered solid was washed with water and Et2O then thoroughly dried under high vacuum to provide the title compound as a beige solid: 1H NMR (300 MHz, DMSO-d6) δ ppm 1.07 (t, J=6.95 Hz, 4 H), 1.56-1.91 (m, 1 H), 3.34-3.41 (m, 7 H), 3.88-3.92 (m, 2 H), 4.11 (s, 2 H), 4.53-4.56 (m, 1 H), 7.12-7.13 (m, 1 H), 7.32-7.37 (m, 2 H), 7.81-7.82 (m, 4 H), 8.14-8.15 (m, 1 H), 8.52 (dd, J=1.47, 0.35 Hz, 1 H), 9.76-10.16 (m, 1 H); ES+ MS: 559 (M+H+).

後処理

  1. filtrationwas filtered
  2. washthe filtered solid was washed with water and Et2O
  3. customthen thoroughly dried under high vacuum

出典と根拠

ORDレコード
ord-0f02aa6b84f84abeb5def9fc18a87bb9
出典データセット
uspto-grants-2014_04
特許番号
US08691991B2

反応ノート

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