Imidazole → HCID 66633620, compound

HRID 931823Notes

Reaction equation

[C:1]([O:7][CH2:8][C@@H:9]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])[C:10]1[C:11]([C:29]2[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=2)=[C:12]2[C:17](=[CH:18][C:19]=1[CH3:20])[N:16]=[C:15](OS(C(F)(F)F)(=O)=O)[CH:14]=[CH:13]2)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].[NH:41]1[CH:45]=[CH:44][N:43]=[CH:42]1>COCCOC>[C:1]([O:7][CH2:8][C@@H:9]([O:36][C:37]([CH3:38])([CH3:40])[CH3:39])[C:10]1[C:11]([C:29]2[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=2)=[C:12]2[C:17](=[CH:18][C:19]=1[CH3:20])[N:16]=[C:15]([N:41]1[CH:45]=[CH:44][N:43]=[CH:42]1)[CH:14]=[CH:13]2)(=[O:6])[C:2]([CH3:4])([CH3:5])[CH3:3]

Participants

Conditions

Temperature: 95 °C

Procedure

To a solution of (S)-2-tert-butoxy-2-(5-(4-chlorophenyl)-7-methyl-2-(trifluoromethylsulfonyloxy)quinolin-6-yl)ethyl pivalate (compound of Example 26) (200 mg, 0.332 mmol) in 1,2-dimethoxyethane was added imidazole (226 mg, 3.32 mmol) and the reaction was sealed and heated to 95° C. overnight. The crude reaction mixture was absorbed onto silica gel and purified by flash column chromatography (silica gel, ethyl acetate/hexanes) to give a yellow oil (33.2 mg). LCMS-ESI+ (m/z): [M+H]+ calcd for C30H35ClN3O3: 520.23. found: 520.35.

Workup

customthe reaction was sealed
customThe crude reaction mixture
customwas absorbed onto silica gel
custompurified by flash column chromatography (silica gel, ethyl acetate/hexanes)

Sources & evidence

ORD record: ord-fc67e247cefb4ae19308a7402fae9299
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09296758B2

Reaction notes

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