N-(3-Aminopropyl)morpholine → 1-[2-(1,3-Dioxo-1,3-dihydro-2H-isoindol-2-yl)ethyl]-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-[3-(4-morpholinyl)propyl]-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide [3-(4-morpholinyl)propyl]amine

HRID 2364383노트

반응식

HRID 2364383 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].[N:39]1([CH2:45][CH2:46][CH2:47][NH2:48])[CH2:44][CH2:43][O:42][CH2:41][CH2:40]1>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:48][CH2:47][CH2:46][CH2:45][N:39]2[CH2:44][CH2:43][O:42][CH2:41][CH2:40]2)=[O:34])[C:15]1=[O:38].[N:39]1([CH2:45][CH2:46][CH2:47][NH2:48])[CH2:44][CH2:43][O:42][CH2:41][CH2:40]1

참가 물질

4

반응물 2

HCID 61055N-(3-Aminopropyl)morpholineHCID 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 694827121-[2-(1,3-Dioxo-1,3-dihydro-2H-isoindol-2-yl)ethyl]-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-[3-(4-morpholinyl)propyl]-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide [3-(4-morpholinyl)propyl]amine

시약·촉매·용매 1

HCID 702Ethanol용매

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 [3-(4-morpholinyl)propyl]amine (0.035 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 1.5 (m, 4 H), 2.2 (t, J=7.0 Hz, 2 H), 2.3 (m, 1 H), 2.6 (t, J=6.9 Hz, 2 H), 3.2 (q, J=6.5 Hz, 2 H), 3.5 (q, J=4.9 Hz, 8 H), 3.9 (t, J=5.5 Hz, 2 H), 4.1 (s, 2 H), 4.5 (t, J=5.6 Hz, 2 H), 7.1 (ddd, J=9.1, 6.7, 2.1 Hz, 2 H), 7.3 (m, 2 H), 7.8 (m, 4 H), 8.1 (s, 1 H), 8.4 (t, J=1.1 Hz, 1 H), 10.0 (t, J=6.0 Hz, 1 H); ES+ MS: 614 (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-1a178bbda07146ffa7d09d23b9d3926d
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08691991B2

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