Triethylamine → Methyl 2,4-dimethyl-5-(3a,4,6,6a-tetrahydro-1H-furo[3,4-d]imidazol-2-yl)benzoate

HRID 541480Notes

Reaction equation

[O:1]1[CH2:5][CH:4]([NH2:6])[CH:3]([NH2:7])[CH2:2]1.Cl.N=[C:10](OC)[C:11]1[C:12]([CH3:22])=[CH:13][C:14]([CH3:21])=[C:15]([CH:20]=1)[C:16]([O:18][CH3:19])=[O:17].C(N(CC)CC)C>C(O)C>[CH3:21][C:14]1[CH:13]=[C:12]([CH3:22])[C:11]([C:10]2[NH:7][CH:3]3[CH2:2][O:1][CH2:5][CH:4]3[N:6]=2)=[CH:20][C:15]=1[C:16]([O:18][CH3:19])=[O:17]

Participants

Conditions

Temperature: 80 °C

Procedure

Into around-bottom flask, was placed a solution of tetrahydrofuran-3,4-diamine (compound 466.3, 140 mg, 1.17 mmol, 1.00 equiv, 85%) in ethanol (6 mL). Methyl 5-(imino(methoxy)methyl)-2,4-dimethylbenzoate hydrochloride (compound 466.4, 300 mg, 0.930 mmol, 1.00 equiv) and triethylamine (140 mg, 1.38 mmol, 1.00 equiv) were added and the resulting solution was stirred overnight at 80° C., then concentrated in vacuo. The residue was purified by silica gel chromatography with dichloromethane/methanol (10:1) as the eluent to obtain the title compound as a brown oil (120 mg, 34%).

Workup

customInto around-bottom flask, was placed
concentrationconcentrated in vacuo
customThe residue was purified by silica gel chromatography with dichloromethane/methanol (10:1) as the eluent

Sources & evidence

ORD record: ord-f19c24170b1c45d5b84a02beabdb489f
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08871790B2

Reaction notes

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