Hydrochloric Acid → 3-[2-Fluoro-5-(4-oxo-3,4,5,6,7,8-hexahydro-phthalazin-1-ylmethyl)-phenyl]-5-methylimidazolidine-2,4-dione

HRID 1012957Notes

Reaction equation

HRID 1012957 reaction equation
C[O:2][C:3](=O)[CH:4]([NH:6][C:7]([NH:9][C:10]1[CH:15]=[C:14]([CH2:16][C:17]2[C:26]3[CH2:25][CH2:24][CH2:23][CH2:22][C:21]=3[C:20](=[O:27])[NH:19][N:18]=2)[CH:13]=[CH:12][C:11]=1[F:28])=[O:8])[CH3:5].[OH-].[Na+].Cl>CC(N(C)C)=O>[F:28][C:11]1[CH:12]=[CH:13][C:14]([CH2:16][C:17]2[C:26]3[CH2:25][CH2:24][CH2:23][CH2:22][C:21]=3[C:20](=[O:27])[NH:19][N:18]=2)=[CH:15][C:10]=1[N:9]1[C:3](=[O:2])[CH:4]([CH3:5])[NH:6][C:7]1=[O:8]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 577866402-{3-[2-Fluoro-5-(4-oxo-3,4,5,6,7,8-hexahydro-phthalazin-1-ylmethyl)-phenyl]-ureido}-propionic Acid Methyl Ester

Product 1

HCID 577866443-[2-Fluoro-5-(4-oxo-3,4,5,6,7,8-hexahydro-phthalazin-1-ylmethyl)-phenyl]-5-methylimidazolidine-2,4-dione

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

To a solution of 2-{3-[2-fluoro-5-(4-oxo-3,4,5,6,7,8-hexahydro-phthalazin-1-ylmethyl)-phenyl]-ureido}-propionic acid methyl ester (12) (0.425 g, 1.053 mmol), in dry DMA (5 ml), was added ground sodium hydroxide (0.433 mg, 1.053 mmol) in one portion. The reaction mixture was then placed in a preheated oil bath at 50° C. for 10 minutes and neutralised by addition of HCl (2N, ca 1 ml). The mixture was then concentrated to dryness and subjected to flash chromatography, eluent neat ethyl acetate (Rf=0.15). Single peak in LC-MS, (0.457 g, 99% purity); 1H NMR (300 MHz, D6 DMSδ ppm 12.61 (s, 1H), 8.51 (s, 1H), 7.40-7.15 (m, 3H), 4.32 (m, 1H), 3.93 (s, 2H), 2.46 (m, 4H), 1.63 (s, 4H), 1.35 (d, J=6.94 Hz, 3H). M/z (LC-MS, ESP), RT=3.28 mins (M+H 371.1).

Workup

  1. concentrationThe mixture was then concentrated to dryness

Sources & evidence

ORD record
ord-7820e88674f64179962efc38a31fda13
Source dataset
uspto-grants-2011_07
Patent number
US07981890B2

Reaction notes

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