Acetic Acid → 8-benzyl-3-(2,5-dimethyl-1H-pyrrol-1-yl)-6,7,8,9-tetrahydropyrazino[2,3-f][1,4]oxazepine

HRID 1879735Notes

Reaction equation

[CH2:1]([N:8]1[CH2:14][C:13]2[N:15]=[CH:16][C:17]([NH2:19])=[N:18][C:12]=2[O:11][CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:20][C:21](=O)[CH2:22][CH2:23][C:24](=O)[CH3:25].C(O)(=O)C.C1(C)C=CC=CC=1>C(OCC)(=O)C>[CH2:1]([N:8]1[CH2:14][C:13]2[N:15]=[CH:16][C:17]([N:19]3[C:24]([CH3:25])=[CH:23][CH:22]=[C:21]3[CH3:20])=[N:18][C:12]=2[O:11][CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 8-benzyl-6,7,8,9-tetrahydropyrazino[2,3-f][1,4]oxazepin-3-amine (100 mg), 2,5-hexanedione (50 μL), acetic acid (164 μL) and toluene (3 mL) was stirred at 80° C. for 24 hr. The mixture was diluted with ethyl acetate at room temperature, and the organic layer was washed with water and saturated brine, dried over magnesium sulfate, and concentrated. The residue was purified by silica gel column chromatography (solvent gradient: 10→100% ethyl acetate/hexane) to give the title compound (60 mg, 46%) as a pale-yellow oil.

Workup

washthe organic layer was washed with water and saturated brine
dry with materialdried over magnesium sulfate
concentrationconcentrated
customThe residue was purified by silica gel column chromatography (solvent gradient: 10→100% ethyl acetate/hexane)

Sources & evidence

ORD record: ord-c082c2269a8e4512bb549c3cf24054af
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08318722B2

Reaction notes

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