Cesium carbonate → HCID 178468935, compound

HRID 410361Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:16])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH2:12][CH2:13][CH2:14]Cl)[CH:6]=1)[CH3:2].C([O-])([O-])=O.[Cs+].[Cs+].[NH:23]1[C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=2[NH:25][C:24]1=[NH:32]>CN(C=O)C>[CH2:1]([O:3][C:4](=[O:16])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH2:12][CH2:13][CH2:14][N:23]2[C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=3[NH:25][C:24]2=[NH:32])[CH:6]=1)[CH3:2]

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 3-(3-chloro-propoxy)-benzoic acid ethyl ester (5.50 g, 22.7 mmol) in DMF (150 ml) at rt was added Cs2CO3 (14.8 g, 45.5 mmol) and 1,3-dihydro-benzoimidazol-2-ylidene amine (2.75 g, 20.7 mmol). The reaction was heated to 50° C. for 12 h. After this time, the resulting mixture was cooled to rt and partitioned between EtOAc and H2O. The organic layer was separated and the aqueous phase was extracted with additional EtOAc. The combined organic fractions were washed with brine, dried (Na2SO4), filtered and concentrated under redcued pressure. The crude product was purified by chromatography on silica eluting with 2% MeOH/dichloromethane to give 3-[3-(2-imino-2,3-dihydro-benzoimidazol-1-yl)-propoxy]-benzoic acid ethyl ester (4.9 g g, 64%). HPLC-MS 340 [M+1]+.

Workup

temperatureAfter this time, the resulting mixture was cooled to rt
custompartitioned between EtOAc and H2O
customThe organic layer was separated
extractionthe aqueous phase was extracted with additional EtOAc
washThe combined organic fractions were washed with brine
dry with materialdried (Na2SO4)
filtrationfiltered
concentrationconcentrated under redcued pressure
customThe crude product was purified by chromatography on silica eluting with 2% MeOH/dichloromethane

Sources & evidence

ORD record: ord-82bbba30d6a644f394bb1510eb7f20f4
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08759520B2

Reaction notes

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