Hydroxyamine hydrochloride → 4-[2-Amino-4-[3-(2-fluoropyridin-3-yl)phenyl]-1-methyl-5-oxo-4,5-dihydro-1H-imidazol-4-yl]-1-(3-fluoropropyl)-1H-pyrrole-2-carbaldehyde oxime

HRID 646262Notes

Reaction equation

[NH2:1][C:2]1[N:3]([CH3:32])[C:4](=[O:31])[C:5]([C:20]2[CH:21]=[C:22]([CH:29]=O)[N:23]([CH2:25][CH2:26][CH2:27][F:28])[CH:24]=2)([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([C:13]3[C:14]([F:19])=[N:15][CH:16]=[CH:17][CH:18]=3)[CH:8]=2)[N:6]=1.Cl.[NH2:34][OH:35]>O1CCCC1>[NH2:1][C:2]1[N:3]([CH3:32])[C:4](=[O:31])[C:5]([C:20]2[CH:21]=[C:22]([CH:29]=[N:34][OH:35])[N:23]([CH2:25][CH2:26][CH2:27][F:28])[CH:24]=2)([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([C:13]3[C:14]([F:19])=[N:15][CH:16]=[CH:17][CH:18]=3)[CH:8]=2)[N:6]=1

Participants

Conditions

Temperature: 45 °C

Procedure

A solution of 4-{2-amino-4-[3-(2-fluoropyridin-3-yl)phenyl]-1-methyl-5-oxo-4,5-dihydro-1H-imidazol-4-yl}-1-(3-fluoropropyl)-1H-pyrrole-2-carbaldehyde in dry tetrahydrofuran was treated with 1.1 equivalent of hydroxylamine hydrochloride, warmed to 45° C. for 2 hours and concentrated in vacuo. The resultant residue was dissolved in chloroform, washed with water, dried over sodium sulfate and concentrated in vacuo. This residue was purified by HPLC (CN bonded stationary phase, gradient 30% to 60% of (20% MeOH/methylene chloride) and hexane to afford the title compound as a white amorphous solid, mp 119-123° C., identified by NMR and mass spectral analyses.

Workup

concentrationconcentrated in vacuo
dissolutionThe resultant residue was dissolved in chloroform
washwashed with water
dry with materialdried over sodium sulfate
concentrationconcentrated in vacuo
customThis residue was purified by HPLC (CN

Sources & evidence

ORD record: ord-9f17324f50304fc284cbe0ccdf596a55
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07705030B2

Reaction notes

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