Potassium Carbonate → Methyl 4-methyl-3-(3,4,6,7-tetrahydropyrano[3,4-d]imidazol-2-yl)benzoate

HRID 541186Notes

Reaction equation

[C:1]([C:4]1[CH:5]=[C:6]([CH:11]=[CH:12][C:13]=1[CH3:14])[C:7]([O:9][CH3:10])=[O:8])(=[NH:3])[NH2:2].Br[CH:16]1[C:21](=O)[CH2:20][CH2:19][O:18][CH2:17]1.C(=O)([O-])[O-].[K+].[K+]>CC#N>[CH3:14][C:13]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][C:4]=1[C:1]1[NH:2][C:16]2[CH2:17][O:18][CH2:19][CH2:20][C:21]=2[N:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of methyl 3-carbamimidoyl-4-methylbenzoate (compound 1.9, 400 mg, 1.98 mmol, 1.00 equiv, 95%), 3-bromodihydro-2H-pyran-4(3H)-one (compound 1.10.1, 750 mg, 2.09 mmol, 1.00 equiv), and potassium carbonate (580 mg, 4.20 mmol, 2.00 equiv) in CH3CN (15 mL) was stirred overnight at 80° C. under nitrogen. After cooling to ambient temperature, the reaction mixture was concentrated under reduced pressure. The residue was dissolved in 50 mL of ethyl acetate and washed with 2×10 mL of H2O. The organic phase was dried over (Na2SO4) and concentrated under reduced pressure. The residue was purified using silica gel column chromatography and purified using ethyl acetate/petroleum ether (1/3) to yield 0.21 g (37%) of the title compound as a white solid.

Workup

temperatureAfter cooling to ambient temperature
concentrationthe reaction mixture was concentrated under reduced pressure
dissolutionThe residue was dissolved in 50 mL of ethyl acetate
washwashed with 2×10 mL of H2O
dry with materialThe organic phase was dried over (Na2SO4)
concentrationconcentrated under reduced pressure
customThe residue was purified
custompurified

Sources & evidence

ORD record: ord-5c97ef009abb4308a55aee8424e0fe71
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08871790B2

Reaction notes

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