2-Morpholinoethylamine → HCID 69482804, compound

HRID 2364395Notes

Reaction equation

HRID 2364395 reaction equation
[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][NH2:47])[CH2:44][CH2:43][O:42][CH2:41][CH2:40]1>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: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]

Participants

4

Reactant 2

HCID 4082852-MorpholinoethylamineHCID 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

Product 1

HCID 69482804HCID 69482804, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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 (1 mL) under nitrogen was treated with 2-(4-morpholinyl)ethanamine (0.008 mL, 0.061 mmol) for 30 min.@150° C. The reaction was further microwaved for 30 min.@150° C. after the addition of an additional equivalent (0.008 mL) of the amine, cooled to ambient temperature, and the resulting suspension was filtered, washed with EtOH and then thoroughly dried under high vacuum to provide the title compound as an off-white solid: 1H NMR (300 MHz, DMSO-d6) δ ppm 2.26-2.34 (m, 6 H), 3.33-3.37 (m, 2 H), 3.48-3.54 (m, 4 H), 3.91 (t, J=5.69 Hz, 2 H), 4.13 (s, 2 H), 4.56 (t, J=5.62 Hz, 2 H), 7.10-7.17 (m, 2 H), 7.33-7.40 (m, 2 H), 7.82 (s, 4 H), 8.16 (d, J=1.12 Hz, 1 H), 8.53 (d, J=0.84 Hz, 1 H), 10.04 (t, J=6.18 Hz, 1 H); ES+ MS: 600 (N+H+).

Workup

  1. customThe reaction was further microwaved for 30 min.@150° C.
  2. filtrationthe resulting suspension was filtered
  3. washwashed with EtOH
  4. customthoroughly dried under high vacuum

Sources & evidence

ORD record
ord-82cb6c41148d4650bc848cb9219195a4
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

Loading…