Formic Acid → HCID 86611506, compound

HRID 1454711Notes

Reaction equation

C(O[C:5](=[O:7])C)(=O)C.C(O)=O.[Cl:11][C:12]1[C:13]([NH2:32])=[CH:14][C:15]2[N:19]=[C:18]([CH2:20][CH3:21])[N:17]([C:22]3[CH:27]=[CH:26][C:25]([CH2:28][CH2:29][Cl:30])=[CH:24][CH:23]=3)[C:16]=2[CH:31]=1>C1COCC1>[Cl:11][C:12]1[C:13]([NH:32][CH:5]=[O:7])=[CH:14][C:15]2[N:19]=[C:18]([CH2:20][CH3:21])[N:17]([C:22]3[CH:23]=[CH:24][C:25]([CH2:28][CH2:29][Cl:30])=[CH:26][CH:27]=3)[C:16]=2[CH:31]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A solution of acetic anhydride (0.14 ml) in THF (5 ml) was added formic acid (0.06 ml, 1.65 mmol) at 0° C. under nitrogen and the mixture was stirred at 60° C. for 2 h. Then the mixture was recooled to 0° C. and was added 6-Chloro-1-[4-(2-chloroethyl)phenyl]-2-ethyl-1H-benzimidazol-5-ylamine (Example 110, step 6, 100 mg, 0.3 mmol) in THF (2 ml). The mixture was stirred at room temperature for 2 h. The volafile component was removed under reduced pressure, and the residue was dissolved with ethyl acetate (100 ml). The organic layer was washed with 2N aqueous NaOH (50 ml), brine (50 ml), then dried (Na2SO4). After removal of solvent, the crude product was purified by flash column chromatography eluting with hexane/ethyl acetate (1:10) to afford 68 mg (67%) of the title compound as pale yellow solids.

Workup

customwas recooled to 0° C.
stirringThe mixture was stirred at room temperature for 2 h
customThe volafile component was removed under reduced pressure
dissolutionthe residue was dissolved with ethyl acetate (100 ml)
washThe organic layer was washed with 2N aqueous NaOH (50 ml), 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 (1:10)

Sources & evidence

ORD record: ord-4e8b52d7e9674b3fb901068150e1588b
Source dataset: uspto-grants-2009_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07479564B2

Reaction notes

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