2,2,2-Trifluoroethyl trifluoromethanesulfonate → HCID 69482202, compound

HRID 2364321Notes

Reaction equation

HRID 2364321 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]2[CH:18]=[C:17]3[C:12]([C:13]([OH:25])=[C:14]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:15](=[O:19])[NH:16]3)=[N:11][CH:10]=2)=[CH:4][CH:3]=1.FC(F)(F)S(O[CH2:32][C:33]([F:36])([F:35])[F:34])(=O)=O>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]2[CH:18]=[C:17]3[C:12]([C:13]([OH:25])=[C:14]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:15](=[O:19])[N:16]3[CH2:32][C:33]([F:36])([F:35])[F:34])=[N:11][CH:10]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 803662,2,2-Trifluoroethyl trifluoromethanesulfonateHCID 54729997Ethyl 7-[(4-Fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate

Product 1

HCID 69482202HCID 69482202, compoundYield 95%

Procedure

In a similar manner to that described in example 316 step 1, from ethyl 7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate (50 mg, 0.146 mmol), lithium (bis-trimethylsilyl)amide (49 mg, 0.292 mmol), and 2,2,2-trifluoroethyl trifluoromethanesulfonate (0.2 mL, 0.876 mmol) was prepared ethyl 7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1-(2,2,2-trifluoroethyl)-1,2-dihydro-1,5-naphthyridine-3-carboxylate (58 mg, 95% yield) as a yellow oil. 1H NMR (CDCl3) δ 8.54 (s, 1 H), 7.37 (s, 1 H), 7.16-7.12 (m, 2 H), 7.04-6.97 (m, 2 H), 4.83 (m, 2 H), 4.49 (m, 2 H), 4.13 (s, 2 H), 1.46 (m, 3 H); MS m/z 425 M+1).

Sources & evidence

ORD record
ord-247d4f6208954dd8be169e7e4e33dd2f
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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