Trifluoroacetic acid → (2S)-3-(2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-yloxy)-2-ethylpentan-1-amine

HRID 876398Notes

Reaction equation

[N:1]1[N:2]=[C:3]([C:10]2[CH:19]=[CH:18][C:17]3[C:12](=[C:13]([O:20][CH:21]([CH2:34][CH3:35])[C@@H:22]([CH2:32][CH3:33])[CH2:23][NH:24]C(=O)OC(C)(C)C)[CH:14]=[CH:15][CH:16]=3)[N:11]=2)[N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12.C(O)(C(F)(F)F)=O>C(Cl)Cl>[N:1]1[N:2]=[C:3]([C:10]2[CH:19]=[CH:18][C:17]3[C:12](=[C:13]([O:20][CH:21]([CH2:34][CH3:35])[C@@H:22]([CH2:32][CH3:33])[CH2:23][NH2:24])[CH:14]=[CH:15][CH:16]=3)[N:11]=2)[N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12

Participants

Conditions

Temperature: 0 °C

Procedure

tert-Butyl (2S)-3-(2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-yloxy)-2-ethylpentylcarbamate was dissolved in 5 mL DCM and cooled to 0° C. TFA (5 mL) was added and the mixture was allowed to warm to ambient temperature over 1 hour. The reaction mixture was evaporated to dryness, and the residue was dissolved in 30 mL DCM and washed with 1N NaOH. The combined organic layers were dried over Na2SO4, filtered, and concentrated under vacuum. The residue was purified by silica gel chromatography followed by preparative TLC to give the desired product (42.5 mg, 29%). MS ESI (+) m/z 376.1 (M+1) detected.

Workup

temperatureto warm to ambient temperature over 1 hour
customThe reaction mixture was evaporated to dryness
dissolutionthe residue was dissolved in 30 mL DCM
washwashed with 1N NaOH
dry with materialThe combined organic layers were dried over Na2SO4
filtrationfiltered
concentrationconcentrated under vacuum
customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record: ord-175c7277cd4f4043b80251def98022ee
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08987251B2

Reaction notes

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