Water → HCID 67099223, compound

HRID 724178Notes

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-76e3ea8f7eeb490b8a05d8c4f931a5a9
Source dataset: uspto-grants-2006_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07141580B2

Reaction notes

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