Hydrazine → HCID 69482180, compound

HRID 2364408Notes

Reaction equation

HRID 2364408 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].[N:39]1([CH2:45][CH2:46][NH2:47])[CH2:44][CH2:43][O:42][CH2:41][CH2:40]1.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:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=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

6

Reactant 3

HCID 9321HydrazineHCID 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 69482180HCID 69482180, 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-(4-morpholinyl)ethanamine (0.321 mL, 2.44 mmol) for 30 min. (150° C. in a microwave vessel. The reaction was further microwaved for an additional 30 min.@150° C. after the addition of another equivalent (0.064 mL) of the amine. The reaction was transferred 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 a pale yellow solid: 1H NMR (300 MHz, DMSO-d6) δ ppm 2.27 (s, 1 H), 2.39-2.46 (m, 5 H), 2.70-2.81 (m, 2 H), 3.40-3.53 (m, 1 H), 3.57-3.61 (m, 6 H), 4.16 (s, 2 H), 4.18-4.26 (m, 2 H), 7.10-7.17 (m, 2 H), 7.35-7.41 (m, 2 H), 8.13-8.15 (m, 1 H), 8.50-8.51 (m, 1 H), 10.36-10.43 (m, 1 H); ES+ MS: 470 (M+H+).

Workup

  1. customThe reaction was further microwaved for an additional 30 min.
  2. custom@150° C.
  3. customThe reaction was transferred to a test tube
  4. filtrationThe resulting suspension was filtered
  5. washwashed with 2:1 water
  6. dry with materialEtOH and thoroughly dried under high vacuum

Sources & evidence

ORD record
ord-d93cbf299f5646aba31d2272238d04fd
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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