Trifluoroacetic acid → HCID 178425982, compound

HRID 1615653Notes

Reaction equation

FC(F)(F)C(O)=O.[C:8]1([CH3:28])[CH:13]=[C:12]([CH3:14])[CH:11]=[C:10]([CH3:15])[C:9]=1[S:16]([O:19][NH:20]C(=O)OC(C)(C)C)(=[O:18])=[O:17].[N:29]1[C:38]2[CH:37]=[CH:36][N:35]=[C:34]([NH2:39])[C:33]=2[CH:32]=[CH:31][CH:30]=1>C(Cl)Cl>[NH2:20][N:35]1[CH:36]=[CH:37][C:38]2[N:29]=[CH:30][CH:31]=[CH:32][C:33]=2[C:34]1=[NH2+:39].[CH3:15][C:10]1[CH:11]=[C:12]([CH3:14])[CH:13]=[C:8]([CH3:28])[C:9]=1[S:16]([O-:19])(=[O:18])=[O:17]

Participants

Conditions

Temperature: 0 °C

Procedure

To trifluoroacetic acid (10 mL), stirred at 0° C., was added tert-butyl mesitylsulfonyloxycarbamate (6.50 g, 20.6 mmol), and the mixture was stirred at 0° C. for 30 min. The mixture was poured into ice-water (10 mL). A white precipitate was formed, which was filtered and collected. The white precipitate was dissolved in DCM (20 mL), and dried with Na2SO4. To the DCM solution was added 1,6-naphthyridin-5-amine (1.0 g, 6.88 mmol), and the mixture was stirred at room temperature for 4 h. The solvent was removed under reduced pressure and the residue was washed with Et2O (3×15 mL). The yellow solid obtained was used in the next step without further purification (3.30 g). ESI MS: m/z 161 [M+H]+.

Workup

customA white precipitate was formed
filtrationwhich was filtered
customcollected
dissolutionThe white precipitate was dissolved in DCM (20 mL)
dry with materialdried with Na2SO4
stirringthe mixture was stirred at room temperature for 4 h
customThe solvent was removed under reduced pressure
washthe residue was washed with Et2O (3×15 mL)
customThe yellow solid obtained
customwas used in the next step without further purification (3.30 g)

Sources & evidence

ORD record: ord-78d29409061b4259a66ee0da5ea22ebd
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765760B2

Reaction notes

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