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

HRID 600274Notes

Reaction equation

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

Participants

Conditions

Temperature: 60 °C

Procedure

{3-[2-Fluoro-5-(4-oxo-3,4-dihydro-phthalazin-1-ylmethyl)-phenyl]-5-methyl-2,4-dioxo-imidazolidin-1-yl}-acetic acid methyl ester (39)(0.03 g, 0.068 mmol) was dissolved in solution of 7N ammonia in methanol (2 ml, 14 mmol) and placed in a sealed tube. The reaction was then heated to 60° C. for 18 hours. The resultant solution was concentrated in vacuo absorbed onto a 1 ml silica cartridge. The material was eluted with neat ethyl acetate. RF of 0.65 yielding pure amide product. Single peak in LC-MS, (8 mg, 100% purity) and required no further purification; m/z (LC-MS, ESP), RT=2.84 mins (M+H) 424;

Workup

customplaced in a sealed tube
concentrationThe resultant solution was concentrated in vacuo
customabsorbed onto a 1 ml silica cartridge
washThe material was eluted with neat ethyl acetate
customno further purification

Sources & evidence

ORD record: ord-932d4c05fd124baf8ded8a52f12c58c8
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07902193B2

Reaction notes

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