Trifluoroacetic acid → HCID 57671528, compound

HRID 553524Notes

Reaction equation

[C:1]1([C:7]2[CH:8]=[C:9]3[C:14](=[N:15][CH:16]=2)[N:13]([CH3:17])[C:12](=[O:18])[C:11]([C:19]([NH:21][CH2:22][C:23]([O:25]C(C)(C)C)=[O:24])=[O:20])=[C:10]3[OH:30])[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1.C(O)(C(F)(F)F)=O>>[C:1]1([C:7]2[CH:8]=[C:9]3[C:14](=[N:15][CH:16]=2)[N:13]([CH3:17])[C:12](=[O:18])[C:11]([C:19]([NH:21][CH2:22][C:23]([OH:25])=[O:24])=[O:20])=[C:10]3[OH:30])[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 57671662HCID 57671662, compound

Product 1

HCID 57671528HCID 57671528, compound

Procedure

The title compound was prepared similarly to the procedure described for Example 1 (g) by treatment of tert-butyl 2-(6-cyclohexenyl-4-hydroxy-1-methyl-2-oxo-1,2-dihydro-1,8-naphthyridine-3-carboxamido)acetate (Example 66 (a)) with TFA. MS (ESI, pos. ion) m/z: 357 (M+1). 1H NMR (300 MHz, DMSO-d6) δ ppm: 10.48 (t, J=5.6 Hz, 1 H), 8.93 (d, J=2.3 Hz, 1 H), 8.28 (d, J=1.9 Hz, 1 H), 6.39 (br. s, 1 H), 4.13 (d, J=5.6 Hz, 2 H), 3.69 (s, 3 H), 2.39-2.46 (m, 2 H), 2.17-2.27 (m, 2 H), 1.70-1.84 (m, 2 H), 1.59-1.69 (m, 2 H).

Sources & evidence

ORD record: ord-d1498dd49419404686adc75666972724
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08048892B2

Reaction notes

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