Hydrazine → HCID 69482715, compound

HRID 2364407Notes

Reaction equation

HRID 2364407 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](OCC)=[O:34])[C:15]1=[O:38].[NH2:39][CH2:40][CH2:41][O:42][CH2:43][CH2:44][OH:45].NN>CCO.O>[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:39][CH2:40][CH2:41][O:42][CH2:43][CH2:44][OH:45])=[O:34])[C:15]1=[O:38]

Participants

6

Reactant 3

HCID 9321HydrazineHCID 13578DiglycolamineHCID 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 69482715HCID 69482715, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

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 (0.252 g, 0.49 mmol) in EtOH (15 mL) under nitrogen was treated with 2-[(2-aminoethyl)oxy]ethanol (0.176 mL, 2.44 mmol) for 15 min.@150° C. in a microwave vessel. Transferred the mixture to a test tube, diluted with EtOH (30 mL), and treated with hydrazine (0.4 mL, 13 mmol)@50° C. overnight. After the reaction was cooled to ambient temperature the resulting suspension was diluted with water (120 mL) and refrigerated overnight. The resulting suspension was filtered, washed with 2:1 water:EtOH and thoroughly dried under high vacuum to provide the title compound as an off-white solid: 1H NMR (300 MHz, DMSO-d6) δ ppm 2.27 (s, 1 H), 2.79 (t, J=6.81 Hz, 2 H), 3.45-3.61 (m, 8 H), 4.12-4.17 (m, 2 H), 4.22 (t, J=6.74 Hz, 2 H), 4.62 (s, 1 H), 7.10-7.18 (m, 2 H), 7.33-7.42 (m, 2 H), 8.07-8.16 (m, 1 H), 8.46-8.54 (m, 1 H), 10.44 (t, J=5.19 Hz, 1 H); ES+ MS: 445 (M+H+).

Workup

  1. filtrationThe resulting suspension was filtered
  2. washwashed with 2:1 water
  3. dry with materialEtOH and thoroughly dried under high vacuum

Sources & evidence

ORD record
ord-bd0f23b3690a401fa92174f166f0c8c7
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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