Methyl {3-[(4-methylphenyl)sulfonyl]-7-nitro-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl}acetate → 1-[(4-Methylphenyl)sulfonyl]-4H-imidazo[1,5,4-de]quinoxaline-2,5(1H,6H)-dione

HRID 551019Notes

Reaction equation

[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[C:15]3[CH:16]=[CH:17][CH:18]=[C:19]([N+:20]([O-])=O)[C:14]=3[N:13]([CH2:23][C:24](OC)=[O:25])[C:12]2=[O:28])(=[O:10])=[O:9])=[CH:4][CH:3]=1>CCOC(C)=O.[Pd]>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[C:15]3[C:14]4[N:13]([CH2:23][C:24](=[O:25])[NH:20][C:19]=4[CH:18]=[CH:17][CH:16]=3)[C:12]2=[O:28])(=[O:9])=[O:10])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of methyl {3-[(4-methylphenyl)sulfonyl]-7-nitro-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl}acetate from Step C (1.00 g, 2.47 mmol) and 10% Pd/C (100 mg) was stirred vigorously in EtOAc (100 mL) under an atmosphere of hydrogen (ca. 1 atm). After 4 h, the mixture was filtered through a pad of Celite, washing with EtOAc (300 mL). To the filtrate was added AcOH (2 mL) and this solution was heated at 80° C. for 1 h, then concentrated in vacuo to give the title compound. MS: m/z=344 (M+1).

Workup

filtrationthe mixture was filtered through a pad of Celite
washwashing with EtOAc (300 mL)
additionTo the filtrate was added AcOH (2 mL)
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-1f61f01efc554811ae8dd2b2cb03ca20
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07947677B2

Reaction notes

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