Sodium Hydroxide → 5-Methyl-3-[3-(4-oxo-3,4,5,6,7,8-hexahydro-phthalazin-1-ylmethyl)-phenyl]-imidazolidine-2,4-dione

HRID 1012951Notes

Reaction equation

HRID 1012951 reaction equation
C([O:3][C:4](=O)[CH:5]([NH:7][C:8]([NH:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([CH2:17][C:18]2[C:27]3[CH2:26][CH2:25][CH2:24][CH2:23][C:22]=3[C:21](=[O:28])[NH:20][N:19]=2)[CH:12]=1)=[O:9])[CH3:6])C.[OH-].[Na+]>CC(N(C)C)=O>[CH3:6][CH:5]1[NH:7][C:8](=[O:9])[N:10]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([CH2:17][C:18]3[C:27]4[CH2:26][CH2:25][CH2:24][CH2:23][C:22]=4[C:21](=[O:28])[NH:20][N:19]=3)[CH:12]=2)[C:4]1=[O:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 57786638HCID 57786638, compound

Product 1

HCID 577866415-Methyl-3-[3-(4-oxo-3,4,5,6,7,8-hexahydro-phthalazin-1-ylmethyl)-phenyl]-imidazolidine-2,4-dione

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

To a solution of 2-{3-[3-(4-oxo-3,4,5,6,7,8-hexahydro-phthalazin-1-ylmethyl)-phenyl]-ureido}-propionic acid ethyl ester (5) (0.715 g, 1.80 mmol) in dry DMA (2 ml) was added finely powdered sodium hydroxide (71 mg, 1.80 mmol). The reaction mixture was then immersed in a preheated oil bath at 50° C. and heated for 10 minutes before being quenched by addition of HCl (1N, 0.5 ml). The reaction mixture was then concentrated to dryness in vacuo. The crude oil was subjected to flash chromatography eluent 4:1, hexane:ethyl acetate (Rf=0.18, neat ethyl acetate). Main peak in LC-MS, (0.25 g, 95% purity); 1H NMR (300 MHz, D6 DMSδ ppm 12.61 (s, 1H), 8.41 (s, 1H), 7.40 (dd, J=11.46, 4.58 Hz, 1H), 7.29-7.12 (m, 2H), 4.32-4.15 (m, 1H), 3.94 (s, 2H), 2.46 (m, 4H), 1.61 (s, 4H), 1.34 (d, J=6.94 Hz, 3H). M/z (LC-MS, ESP), RT=3.04 mins (M+H 353.2).

Workup

  1. customThe reaction mixture was then immersed in a preheated oil bath at 50° C.
  2. temperatureheated for 10 minutes
  3. custombefore being quenched by addition of HCl (1N, 0.5 ml)
  4. concentrationThe reaction mixture was then concentrated to dryness in vacuo

Sources & evidence

ORD record
ord-50ebfe8e761d47b8b42d681961545ba1
Source dataset
uspto-grants-2011_07
Patent number
US07981890B2

Reaction notes

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