Water → HCID 67099223, compound

HRID 858530Notes

Reaction equation

[Cl:1][C:2]1[C:3]([CH2:29]Cl)=[CH:4][C:5]2[N:9]=[C:8]([CH2:10][CH3:11])[N:7]([C:12]3[CH:17]=[CH:16][C:15]([CH2:18][CH2:19][O:20][Si:21]([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22])=[CH:14][CH:13]=3)[C:6]=2[CH:28]=1.[C:31]([OH:35])(=[O:34])[CH2:32][CH3:33].C([O-])(O)=O.[Na+].O>CN(C)C=O>[C:31]([O:35][CH2:29][C:3]1[C:2]([Cl:1])=[CH:28][C:6]2[N:7]([C:12]3[CH:17]=[CH:16][C:15]([CH2:18][CH2:19][O:20][Si:21]([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:22])[CH3:23])=[CH:14][CH:13]=3)[C:8]([CH2:10][CH3:11])=[N:9][C:5]=2[CH:4]=1)(=[O:34])[CH2:32][CH3:33]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 6-chloro-5-(chloromethyl)-1-[4-(2-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}ethyl)phenyl]-2-ethyl-1H-benzimidazole (step 2, 403 mg, 0.86 mmol) in N, N-dimethylformamide (10 ml) was added propionic acid (0.06 ml, 0.86 mmol) and NaHCO3 (144 mg, 1.72 mmol) at room temperature. The mixture was stirred at 60° C. for 7 h. The mixture was added water (50 ml) and extracted with ethyl acetate(100 ml). The organic layer was washed with brine (50 ml), then dried (Na2SO4). After removal of solvent, the crude product was purified by flash column chromatography eluting with hexane/ethyl acetate (8:1/4:1) to afford 235 mg (53%) of the title compound as pale yellow oil.

Workup

extractionextracted with ethyl acetate(100 ml)
washThe organic layer was washed with brine (50 ml)
dry with materialdried (Na2SO4)
customAfter removal of solvent
customthe crude product was purified by flash column chromatography
washeluting with hexane/ethyl acetate (8:1/4:1)

Sources & evidence

ORD record: ord-b41c112b7f214a7fbd48f4f6b0014917
Source dataset: uspto-grants-2006_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07148234B2

Reaction notes

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