Hydrazine → 1-(2-Aminoethyl)-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-{2-[(1-methylethyl)oxy]ethyl}-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide

HRID 2364382Notes

Reaction equation

HRID 2364382 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].[CH3:39][CH:40]([O:42][CH2:43][CH2:44][NH2:45])[CH3:41].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:45][CH2:44][CH2:43][O:42][CH:40]([CH3:41])[CH3:39])=[O:34])[C:15]1=[O:38]

Participants

6

Reactant 3

HCID 9321HydrazineHCID 5338662-(Propan-2-yloxy)ethan-1-amineHCID 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 694825271-(2-Aminoethyl)-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-{2-[(1-methylethyl)oxy]ethyl}-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide

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 (0.143 g, 0.28 mmol) in EtOH (3 mL) under nitrogen was treated with 2-[(1-methylethyl)oxy]ethanamine (0.102 mL, 0.83 mmol) for 50 min. (130° C. in a microwave vessel. The reaction was transferred to a test tube, diluted with EtOH (35 mL), and treated with hydrazine (0.174 mL, 5.55 mmol) for 4 h@50° C. After the reaction was cooled to ambient temperature the resulting suspension was diluted with water (150 mL) and refrigerated overnight. The resulting suspension was filtered, washed with 3:1 water:EtOH and 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 (d, J=6.2 Hz, 6 H), 2.8 (bs, 2 H), 3.3 (s, 2 H), 3.5 (m, 4 H), 3.6 (m, 1 H), 4.2 (s, 2 H), 7.1 (t, J=9.3 Hz, 2 H), 7.4 (dd, J=8.5, 5.4 Hz, 2 H), 8.1 (s, 1 H), 8.5 (s, 1 H), 10.4 (s, 1 H); ES+ MS: 443 (M+H+).

Workup

  1. customThe reaction was transferred to a test tube
  2. filtrationThe resulting suspension was filtered
  3. washwashed with 3:1 water
  4. dry with materialEtOH and thoroughly dried under high vacuum

Sources & evidence

ORD record
ord-e729c5567993436bbf64681ba8bc812a
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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