Potassium Carbonate → HCID 59610196, compound

HRID 71734Notes

Reaction equation

[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[NH:7])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[C:17]([O:21][C:22]([N:24]1[CH2:28][CH2:27][CH2:26][CH:25]1[C:29](=O)[CH2:30]Cl)=[O:23])([CH3:20])([CH3:19])[CH3:18]>O.C1COCC1>[C:17]([O:21][C:22]([N:24]1[CH2:28][CH2:27][CH2:26][CH:25]1[C:29]1[NH:7][C:6]([C:5]2[CH:9]=[CH:10][C:2]([Br:1])=[CH:3][CH:4]=2)=[N:8][CH:30]=1)=[O:23])([CH3:20])([CH3:19])[CH3:18]

Participants

Conditions

Temperature: 65 °C

Procedure

A mixture of 4-Bromo-benzamidine (0.202 g) and potassium carbonate (0.237 g) in H2O (0.286 mL) and THF (1.1 mL) was heated to 65° C. 2-(2-Chloro-acetyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (0.106 g) in THF (0.7 mL) was added over 1 hour and reaction mixture heated at 65° C. for 18 hours. Reaction mixture was concentrated to ˜0.5 mL and extracted with ethyl acetate. Organic layer was washed with H2O, brine and dried (MgSO4), concentrated and purified by flash column chromatography (silica gel, 20 to 100% ethyl acetate/hexanes) to give 2-[2-(4-Bromo-phenyl)-3H-imidazol-4-yl]-pyrrolidine-1-carboxylic acid tert-butyl ester (0.075 g) as an orange film: LCMS-ESI−: calc'd for C18H23BrN3O2: 393.30 (M+H+). Found: 391.8, 393.83 (M+H+).

Workup

customreaction mixture
temperatureheated at 65° C. for 18 hours
customReaction mixture
concentrationwas concentrated to ˜0.5 mL
extractionextracted with ethyl acetate
washOrganic layer was washed with H2O, brine
dry with materialdried (MgSO4)
concentrationconcentrated
custompurified by flash column chromatography (silica gel, 20 to 100% ethyl acetate/hexanes)

Sources & evidence

ORD record: ord-8f5735e9d1cc44198aa610c284e91257
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08822430B2

Reaction notes

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