Trifluoroacetic acid → {3-[2-Fluoro-5-(4-oxo-3,4-dihydro-phthalazin-1-ylmethyl)-phenyl]-5-methyl-2,4-dioxo-imidazolidin-1-yl}-acetic acid

HRID 600272Notes

Reaction equation

HRID 600272 reaction equation
C([O:5][C:6](=[O:35])[CH2:7][N:8]1[CH:12]([CH3:13])[C:11](=[O:14])[N:10]([C:15]2[CH:20]=[C:19]([CH2:21][C:22]3[C:31]4[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=4)[C:25](=[O:32])[NH:24][N:23]=3)[CH:18]=[CH:17][C:16]=2[F:33])[C:9]1=[O:34])(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[F:33][C:16]1[CH:17]=[CH:18][C:19]([CH2:21][C:22]2[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[C:25](=[O:32])[NH:24][N:23]=2)=[CH:20][C:15]=1[N:10]1[C:11](=[O:14])[CH:12]([CH3:13])[N:8]([CH2:7][C:6]([OH:35])=[O:5])[C:9]1=[O:34]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68910449{3-[2-Fluoro-5-(4-oxo-3,4-dihydro-phthalazin-1-ylmethyl)-phenyl]-5-methyl-2,4-dioxo-imidazolidin-1-yl}-acetic acid tert-butyl ester

Product 1

HCID 59856564{3-[2-Fluoro-5-(4-oxo-3,4-dihydro-phthalazin-1-ylmethyl)-phenyl]-5-methyl-2,4-dioxo-imidazolidin-1-yl}-acetic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of {3-[2-fluoro-5-(4-oxo-3,4-dihydro-phthalazin-1-ylmethyl)-phenyl]-5-methyl-2,4-dioxo-imidazolidin-1-yl}-acetic acid tert-butyl ester (35A)(1.3 g, 2.7 mmol) in dry DCM (20 ml) was added trifluoroacetic acid (2 mL, ca 27 mmol) dropwise over 2 minutes. After overnight stirring the reaction mixture was concentrated to dryness and subjected to flash chromatography. Eluent 1% acetic acid in ethyl acetate. The title compound was isolated as a white solid. Single peak in LC-MS analysis, (0.680 mg, 100% purity) and required no further purification; m/z (LC-MS, ESN), RT=2.95 mins (M−H) 423

Workup

  1. concentrationwas concentrated to dryness

Sources & evidence

ORD record
ord-32a6a55cd7f24100ad307df7f385a0ba
Source dataset
uspto-grants-2011_03
Patent number
US07902193B2

Reaction notes

Loading…