Pyridine → HCID 89691230, compound

HRID 2202967Notes

Reaction equation

FC(F)(F)C(OC(=O)C(F)(F)F)=O.[Cl:14][C:15]1[CH:45]=[CH:44][C:18]([CH2:19][O:20][C:21]2[CH:26]=[CH:25][N:24]([C:27]3[CH:28]=[CH:29][C:30]4[N:34]=[C:33]([CH:35]5[CH2:37][CH:36]5[C:38]([NH2:40])=O)[N:32]([CH3:41])[C:31]=4[CH:42]=3)[C:23](=[O:43])[CH:22]=2)=[CH:17][CH:16]=1.N1C=CC=CC=1>C1COCC1>[Cl:14][C:15]1[CH:45]=[CH:44][C:18]([CH2:19][O:20][C:21]2[CH:26]=[CH:25][N:24]([C:27]3[CH:28]=[CH:29][C:30]4[N:34]=[C:33]([CH:35]5[CH2:37][CH:36]5[C:38]#[N:40])[N:32]([CH3:41])[C:31]=4[CH:42]=3)[C:23](=[O:43])[CH:22]=2)=[CH:17][CH:16]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Trifluoroacetic anhydride (0.181 ml) was added to a solution of (1RS,2SR)-2-(6-(4-((4-chlorobenzyl)oxy)-2-oxopyridin-1(2H)-yl)-1-methyl-1H-benzimidazol-2-yl)cyclopropanecarboxamide (195 mg) and pyridine (0.105 ml) in THF (5 ml) at 0° C. The mixture was stirred at 0° C. for 2 h. The mixture was quenched with saturated NaHCO3 solution at 0° C. and extracted with EtOAc. The organic layer was separated, washed with water and brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by silica gel column chromatography (MeOH/EtOAc). The residue was recrystallized from EtOH/hexane to give the title compound (35 mg) as a white solid.

Workup

customThe mixture was quenched with saturated NaHCO3 solution at 0° C.
extractionextracted with EtOAc
customThe organic layer was separated
washwashed with water and brine
dry with materialdried over MgSO4
concentrationconcentrated in vacuo
customThe residue was purified by silica gel column chromatography (MeOH/EtOAc)
customThe residue was recrystallized from EtOH/hexane

Sources & evidence

ORD record: ord-53c16f9d7df1476e93cf7b1850699c9a
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09365540B2

Reaction notes

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