ethyl 1-[2-(4-methoxyphenyl)-2-oxoethyl]-4-nitro-1H-pyrrole-2-carboxylate → 10a-(4-methoxyphenyl)-7-nitro-2,3,10,10a-tetrahydro-1H,5H-imidazo[1,2-a]pyrrolo[1,2-d]pyrazin-5-one

HRID 1753176Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=O)[CH2:10][N:11]2[CH:15]=[C:14]([N+:16]([O-:18])=[O:17])[CH:13]=[C:12]2[C:19]([O:21]CC)=O)=[CH:5][CH:4]=1>O1CCOCC1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]23[NH:16][CH2:14][CH2:15][N:11]2[C:19](=[O:21])[C:12]2[N:11]([CH:15]=[C:14]([N+:16]([O-:18])=[O:17])[CH:13]=2)[CH2:10]3)=[CH:7][CH:8]=1

Participants

Conditions

Temperature: 105 °C

Procedure

Ethyl 1-[2-(4-methoxyphenyl)-2-oxoethyl]-4-nitro-1H-pyrrole-2-carboxylate (610 mg, 1.8 mmol) was mixed with 1,4-dioxane (7 mL) and ethylene-1,2-diamine (1.7 mL) and the mixture heat at 105° C. After 24 hours the reaction was complete (monitored by LCMS). The reaction was concentrated in vacuo and the resultant residue purified by flash chromatography (Biotage SP4, gradient 0-10% MeOH in EtOAc) to give 10a-(4-methoxyphenyl)-7-nitro-2,3,10,10a-tetrahydro-1H,5H-imidazo[1,2-a]pyrrolo[1,2-d]pyrazin-5-one (200 mg, yield 34%). ESI-MI m/z [M+H]+ 328.9.

Workup

concentrationThe reaction was concentrated in vacuo
customthe resultant residue purified by flash chromatography (Biotage SP4, gradient 0-10% MeOH in EtOAc)

Sources & evidence

ORD record: ord-eb64a065146343348608cc07d2a645cb
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09163029B2

Reaction notes

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