Water → 1-(2-Aminoethyl)-N-[2-(ethyloxy)ethyl]-7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide

HRID 2364344Notes

Reaction equation

HRID 2364344 reaction equation
O=C1C2C(=CC=CC=2)C(=O)[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]([NH:35][CH2:36][CH2:37][O:38][CH2:39][CH3:40])=[O:34])[C:15]1=[O:41].NN.O>CCO>[NH2:3][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:35][CH2:36][CH2:37][O:38][CH2:39][CH3:40])=[O:34])[C:15]1=[O:41]

Participants

5

Reactant 3

HCID 962WaterHCID 9321HydrazineHCID 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

Product 1

HCID 694808831-(2-Aminoethyl)-N-[2-(ethyloxy)ethyl]-7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 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 (0.155 g, 0.277 mmol) in EtOH (6.5 mL) under nitrogen was treated with hydrazine (0.218 mL, 6.92 mmol) for 7 h@50° C. The reaction was then cooled to ambient temperature and stirred overnight. After heating an additional 6.5 h@50° C. the resulting solution was poured into water (75 mL), refrigerated and the resulting suspension was filtered and washed with cold 3:1 water:EtOH. The solid was then thoroughly dried under high vacuum to provide the title compound as an off-white solid: 1H NMR (400 MHz, DMSO-D6) δ ppm 1.1 (t, J=7.1 Hz, 3 H), 2.8 (t, J=7.2 Hz, 2 H), 3.5 (q, J=6.9 Hz, 2 H), 3.5 (s, 4 H), 4.2 (s, 2 H), 4.2 (t, J=7.1 Hz, 2 H), 7.1 (t, J=8.8 Hz, 2 H), 7.4 (dd, J=8.7, 5.4 Hz, 2 H), 8.1 (s, 1 H), 8.5 (s, 1 H), 10.4 (s, 1 H); ES+ MS: 429 (M+H+).

Workup

  1. temperatureAfter heating an additional 6.5 h
  2. custom@50° C.
  3. filtrationrefrigerated and the resulting suspension was filtered
  4. washwashed with cold 3:1 water
  5. customThe solid was then thoroughly dried under high vacuum

Sources & evidence

ORD record
ord-42a3cdcac448493ca06ebe154e90f7e7
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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