Chloride → Methyl 7-benzyl-5,6,7,8-tetrahydroimidazo[1,5-a]pyrazine-1-carboxylate

HRID 1971072Notes

Reaction equation

[Cl-].Cl.[CH2:3]([N:10]([CH2:14][C:15]1[N:16]=[CH:17][NH:18][C:19]=1[C:20]([O:22][CH3:23])=[O:21])[CH2:11][CH2:12]Cl)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>C(#N)C>[CH2:3]([N:10]1[CH2:11][CH2:12][N:16]2[CH:17]=[N:18][C:19]([C:20]([O:22][CH3:23])=[O:21])=[C:15]2[CH2:14]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

Conditions

Temperature: 80 °C

Procedure

The chloride, Intermediate 1E (0.97 g, 3.15 mmol) was dissolved in acetonitrile (30 mL) and TEA (1.77 mL, 12.62 mmol) was added drop wise. The resulting mixture was stirred at 80° C. under nitrogen overnight. The mixture was allowed to cool, was filtered and the filtrate was concentrated. The residue was partitioned between DCM and saturated NaHCO3 solution and the phases were separated. The aqueous phase was further extracted with DCM and combined organic extracts were dried over anhydrous MgSO4, filtered and concentrated. The crude residue was purified using normal phase chromatography, eluting with a 0-40% methanol/DCM gradient to provide product Intermediate 1F (0.58 g, 66%) as a brown solid.

Workup

temperatureto cool
filtrationwas filtered
concentrationthe filtrate was concentrated
customThe residue was partitioned between DCM and saturated NaHCO3 solution
customthe phases were separated
extractionThe aqueous phase was further extracted with DCM
dry with materialwere dried over anhydrous MgSO4
filtrationfiltered
concentrationconcentrated
customThe crude residue was purified
washeluting with a 0-40% methanol/DCM gradient

Sources & evidence

ORD record: ord-21083b836e0f41aeab8dadaa8345ed85
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08431565B2

Reaction notes

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