N-(2-Aminoethyl)ethyleneurea → HCID 69480250, compound

HRID 2364403Notes

Reaction equation

HRID 2364403 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]([O:35]CC)=O)[C:15]1=[O:38].[NH2:39][CH2:40][CH2:41][N:42]1[CH2:46][CH2:45][NH:44][C:43]1=[O:47].OS([O-])(=O)=O.[Na+]>CCO>[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: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][N:42]2[CH2:46][CH2:45][NH:44][C:43]2=[O:47])=[O:35])[C:15]1=[O:38]

Participants

5

Reactant 3

HCID 80480N-(2-Aminoethyl)ethyleneureaHCID 516919Sodium BisulfateHCID 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 69480250HCID 69480250, 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 (0.025 g, 0.049 mmol) in EtOH (1 mL) under nitrogen was treated with 1-(2-aminoethyl)-2-imidazolidinone (0.0078 g, 0.03 mmol, 50% W/W in IPA) for 30 min.@150° C. The reaction was further microwaved for 30 min.@150° C. after the addition of an additional 0.6 equivalents (0.015 mL) of the amine, cooled to ambient temperature, and treated with 1N NaHSO4. The resulting suspension was filtered and the filtrate was concentrated in vacuo. The filtrate residue was purified by reversed phase HPLC. Pure fractions were combined and concentrated to afford the title compound as a pale yellow glass: 1H NMR (300 MHz, CHLOROFORM-d) δ ppm 1.82 (s, 1 H), 3.38-3.51 (m, 4 H), 3.52-3.65 (m, 4 H), 4.00 (t, J=6.67 Hz, 2 H), 4.04-4.10 (m, 2 H), 4.26 (s, 1 H), 4.46 (t, J=6.74 Hz, 2 H), 6.91-7.04 (m, 2 H), 7.10-7.21 (m, 2 H), 7.70-7.78 (m, 3 H), 7.79-7.85 (m, 2 H), 8.51 (d, J=1.26 Hz, 1 H), 10.24 (t, J=6.04 Hz, 1 H); ES+ MS: 599 (M+H+).

Workup

  1. customThe reaction was further microwaved for 30 min.@150° C.
  2. filtrationThe resulting suspension was filtered
  3. concentrationthe filtrate was concentrated in vacuo
  4. customThe filtrate residue was purified by reversed phase HPLC
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-dee58a7c126f475fa05ef35781d7c68e
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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