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

HRID 2364384
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HRID 2364384 반응식
[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].[O:39]1[CH2:43][CH2:42][CH2:41][CH:40]1[CH2:44][NH2:45]>CCO>[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:26]=[CH:27][C:28]([F:31])=[CH:29][CH:30]=3)[CH:22]=2)[C:17]([OH:32])=[C:16]([C:33]([NH:45][CH2:44][CH:40]2[CH2:41][CH2:42][CH2:43][O:39]2)=[O:34])[C:15]1=[O:38]
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참가 물질

4

반응물 2

HCID 253298TetrahydrofurfurylamineHCID 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

생성물 1

HCID 694820281-[2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethyl]-7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-N-(tetrahydro-2-furanylmethyl)-1,2-dihydro-1,5-naphthyridine-3-carboxamide

시약·촉매·용매 1

HCID 702Ethanol
용매

실험 절차

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 (0.025 g, 0.049 mmol) in EtOH (2.5 mL) under nitrogen was treated with 1-(tetrahydro-2-furanyl)methanamine (0.025 mL, 0.24 mmol) for 40 min. (130° C. in a microwave vessel. The reaction was then cooled to ambient temperature and the resulting suspension was filtered, washed with EtOH and Et2O then thoroughly dried under high vacuum to provide the title compound as a white solid: 1H NMR (300 MHz, DMSO-D6) δ ppm 1.7 (m, 4 H), 3.2 (m, 2 H), 3.6 (m, 2 H), 3.8 (m, 1 H), 3.9 (t, J=5.7 Hz, 2 H), 4.1 (s, 2 H), 4.6 (m, 1 H), 7.1 (m, 2 H), 7.3 (m, 2 H), 7.8 (s, 4 H), 8.2 (s, 1 H), 8.5 (d, J=1.4 Hz, 1 H), 10.0 (t, J=5.8 Hz, 1 H); ES+ MS: 571 (M+H+).

후처리

  1. filtrationthe resulting suspension was filtered
  2. washwashed with EtOH and Et2O
  3. customthen thoroughly dried under high vacuum

출처 및 근거

ORD 기록
ord-1bc268b961f54949a150dc73b92a8b25
출처 데이터셋
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08691991B2

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