Ethanolamine → HCID 69480952, compound

HRID 2364332Notes

Reaction equation

HRID 2364332 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].[CH2:39]([CH2:41][NH2:42])[OH: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:42][CH2:41][CH2:39][OH:40])=[O:34])[C:15]1=[O:38]

Participants

4

Reactant 2

HCID 700EthanolamineHCID 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 69480952HCID 69480952, 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 (0.035 g, 0.068 mmol) in EtOH (3 mL) under nitrogen was treated with Ethanolamine (8 mg, 0.13 mmol) for 2 h@150° C. in a microwave vessel. The reaction was then cooled to ambient temperature and the resulting suspension was filtered, washed with EtOH and Et2O and thoroughly dried under high vacuum to provide the title compound as an orange solid: 1H NMR (300 MHz, DMSO-D6) δ ppm 3.4 (m, 5 H), 3.9 (t, J=6.0 Hz, 2 H), 4.1 (s, 2 H), 4.5 (t, J=5.8 Hz, 2 H), 4.8 (t, J=5.0 Hz, 1 H), 7.1 (ddd, J=9.0, 6.7, 2.2 Hz, 2 H), 7.3 (m, 2 H), 7.8 (m, 4 H), 8.1 (d, J=1.1 Hz, 1 H), 8.5 (d, J=1.3 Hz, 1 H), 10.0 (s, 1 H); ES+ MS: 531 (M+H+).

Workup

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

Sources & evidence

ORD record
ord-81604637891d48dbabe238c4eaecb1ed
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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