Hydrazine → 2-{1-[4-(2-Amino-ethyl)-2-p-tolyl-imidazol-1-yl]-2-methyl-propyl}-3-benzyl-7-chloro-3H-quinazolin-4-one

HRID 490254Notes

Reaction equation

[CH2:1]([N:8]1[C:17](=[O:18])[C:16]2[C:11](=[CH:12][C:13]([Cl:19])=[CH:14][CH:15]=2)[N:10]=[C:9]1[CH:20]([N:24]1[CH:28]=[C:27]([CH2:29][CH2:30][N:31]2C(=O)C3C(=CC=CC=3)C2=O)[N:26]=[C:25]1[C:42]1[CH:47]=[CH:46][C:45]([CH3:48])=[CH:44][CH:43]=1)[CH:21]([CH3:23])[CH3:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.NN>CCO>[NH2:31][CH2:30][CH2:29][C:27]1[N:26]=[C:25]([C:42]2[CH:47]=[CH:46][C:45]([CH3:48])=[CH:44][CH:43]=2)[N:24]([CH:20]([C:9]2[N:8]([CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[C:17](=[O:18])[C:16]3[C:11](=[CH:12][C:13]([Cl:19])=[CH:14][CH:15]=3)[N:10]=2)[CH:21]([CH3:23])[CH3:22])[CH:28]=1

Participants

Conditions

Temperature: 5 °C

Procedure

A solution of 2-(2-{1-[1-(3-benzyl-7-chloro-4-oxo-3,4-dihydro-quinazolin-2-yl)-2-methyl-propyl]-2-p-tolyl-1H-imidazol-4-yl}-ethyl)-isoindole-1,3-dione (278 mg, 0.423 mmol) and anhydrous hydrazine (98 mg, 3.06 mmol) in EtOH (12 mL) was refluxed for 3.0 h. The reaction was cooled to 5° C. and a white precipitate was filtered off. The filtrate was concentrated in vacuo and purified by flash chromatography (silica gel, 90:9:1 methylene chloride:methanol:ammonium hydroxide as eluent) to provide the title compound as a white solid (98.2 mg, 45%). MS(ES+) m/e 526 [M+H]+.

Workup

filtrationa white precipitate was filtered off
concentrationThe filtrate was concentrated in vacuo
custompurified by flash chromatography (silica gel, 90:9:1 methylene chloride:methanol:ammonium hydroxide as eluent)

Sources & evidence

ORD record: ord-480049a35f7a481fb4d076ce55d73a3a
Source dataset: uspto-grants-2009_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07528137B2

Reaction notes

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