Ethyl orthoformate → (S)-2-tert-butoxy-2-(6-(4-chlorophenyl)-8-methyl-[1,2,4]triazolo[4,3-a]quinolin-7-yl)ethanol

HRID 931804Notes

Reaction equation

[C:1]([O:5][C@@H:6]([C:9]1[C:10]([C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=2)=[C:11]2[C:16](=[CH:17][C:18]=1[CH3:19])[N:15]=[C:14]([NH:20][NH2:21])[CH:13]=[CH:12]2)[CH2:7][OH:8])([CH3:4])([CH3:3])[CH3:2].[CH:29](OCC)(OCC)OCC>C(O)CCC.C(OCC)(=O)C>[C:1]([O:5][C@@H:6]([C:9]1[C:10]([C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=2)=[C:11]2[C:16](=[CH:17][C:18]=1[CH3:19])[N:15]1[CH:29]=[N:21][N:20]=[C:14]1[CH:13]=[CH:12]2)[CH2:7][OH:8])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 100 °C

Procedure

The mixture of (S)-2-tert-butoxy-2-(5-(4-chlorophenyl)-2-hydrazinyl-7-methylquinolin-6-yl)ethanol and triethyl orthoformate (0.5 mL) in butanol (5 mL) was heated at 100° C. for 12 hours. The solution was diluted with ethyl acetate, and was washed with 1.0 N sodium hydroxide solution and brine, and dried with sodium sulfate. Concentration and purification by flash column chromatography (hexanes/EtOAc) gave (S)-2-tert-butoxy-2-(6-(4-chlorophenyl)-8-methyl-[1,2,4]triazolo[4,3-a]quinolin-7-yl)ethanol (3.3 mg). LCMS-ESI+ (m/z): [M+H]+ calcd for C23H25ClN3O2: 410.2. Found: 410.2.

Workup

washwas washed with 1.0 N sodium hydroxide solution and brine
dry with materialdried with sodium sulfate
concentrationConcentration and purification by flash column chromatography (hexanes/EtOAc)

Sources & evidence

ORD record: ord-faa2d15987144cc1b8e0238091b5b3e1
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09296758B2

Reaction notes

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