Potassium Carbonate → HCID 59497408, compound

HRID 1747345Notes

Reaction equation

C([O:3][C:4](=[O:20])[CH2:5][CH:6]([N:10]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[NH:12][C:11]1=[O:19])[CH2:7][CH2:8][CH3:9])C.C(=O)([O-])[O-].[K+].[K+].Br[CH2:28][C:29]1[CH:34]=[C:33]([CH3:35])[CH:32]=[CH:31][C:30]=1[CH3:36]>CN(C=O)C>[CH3:36][C:30]1[CH:31]=[CH:32][C:33]([CH3:35])=[CH:34][C:29]=1[CH2:28][N:12]1[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[N:10]([CH:6]([CH2:7][CH2:8][CH3:9])[CH2:5][C:4]([OH:3])=[O:20])[C:11]1=[O:19]

Participants

Conditions

Temperature: 80 °C

Procedure

3-(2-Oxo-2,3-dihydro-benzoimidazol-1-yl)-hexanoic acid ethyl ester (40 mg, 0.145 mmol), prepared as described above, was dissolved in DMF (1 mL), and potassium carbonate (69 mg, 0.50 mmol) was added followed by 2-bromomethyl-1,4-dimethyl-benzene (56.3 mg, 0.28 mmol). The resulting mixture was heated at 80° C. for 4 h, cooled, filtered, and the solution was treated directly with the Amberlyst® resin (524 mg, 0.7 mmol). This reaction mixture was agitated overnight and the resin was then filtered and washed with several portions of methanol. The product was eluted by treating the resin with a 20% solution of formic acid in methanol (2×3 mL) and washing with methanol (2×3 mL). The combined eluant and final wash was evaporated to provide the title compound (25 mg, 47%). LCMS (ESMS): m/z 367 (M+H+).

Workup

temperaturecooled
filtrationfiltered
filtrationthe resin was then filtered
washwashed with several portions of methanol
washThe product was eluted
additionby treating the resin with a 20% solution of formic acid in methanol (2×3 mL)
washwashing with methanol (2×3 mL)
washThe combined eluant and final wash
customwas evaporated

Sources & evidence

ORD record: ord-0495be3b015a4f1daa9828da05c82cc9
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09150556B2

Reaction notes

Loading…