Hydrogen Peroxide → USRE47493, Example 71

HRID 517283Notes

Reaction equation

[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[C:18]3[C:17](=[O:19])[CH2:16][CH2:15][CH2:14][C:13]=3[N:12]([C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[CH:21]=3)[C:11](=[O:30])[N:10]2[C:31]([NH:33][CH:34]2[CH2:39][CH2:38][S:37][CH2:36][CH2:35]2)=[O:32])=[CH:5][CH:4]=1)#[N:2].OO.[O:42]=C1O[C@H]([C@H](CO)O)C([O-])=C1O.[Na+].O>C(O)C.C[Re](=O)(=O)=O>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([CH:9]2[C:18]3[C:17](=[O:19])[CH2:16][CH2:15][CH2:14][C:13]=3[N:12]([C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[CH:21]=3)[C:11](=[O:30])[N:10]2[C:31]([NH:33][CH:34]2[CH2:35][CH2:36][S:37](=[O:42])[CH2:38][CH2:39]2)=[O:32])=[CH:7][CH:8]=1)#[N:2]

Participants

Conditions

Temperature: -78 °C

Procedure

A solution of 4-(4-cyanophenyl)-2,5-dioxo-N-(tetrahydro-2H-thiopyran-4-yl)-1-(3-(tri-fluoromethyl)phenyl)-1,2,5,6,7,8-hexahydroquinazoline-3(4H)-carboxamide (intermediate 60, 131 mg, 0.24 mmol) in ethanol (10 mL) is cooled at −78° C. with an acetone/dry ice bath. Aqueous hydrogen peroxide (1 M, 50 μL, 0.05 mmol) is added, and the mixture is stirred at −78° C. for 30 min. Methyltrioxorhenium(VII) (1 mg, 4 μmol) is added, and the mixture is stirred at −78° C. for 2 h. Aqueous sodium ascorbate (10%, 30 mL) and water (30 mL) is added, and the precipitate is filtered and purified by preparative HPLC (Waters Xbridge™-C18, gradient of acetonitrile in water, 0.1% NH3). Yield: 22 mg; ESI mass spectrum [M+H]+=571; Retention time HPLC: 0.51 min (004_CA07).

Workup

stirringthe mixture is stirred at −78° C. for 2 h
filtrationthe precipitate is filtered
custompurified by preparative HPLC (Waters Xbridge™-C18, gradient of acetonitrile in water, 0.1% NH3)
custom0.51 min (004_CA07)

Sources & evidence

ORD record: ord-d291b2293aa34716bbed8491923be874
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09115093B2

Reaction notes

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