Trifluoroacetic acid → HCID 57671543, compound

HRID 553527Notes

Reaction equation

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

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 57671481HCID 57671481, compound

Product 1

HCID 57671543HCID 57671543, compound

Procedure

The title compound was prepared similarly to the procedure described for Example 1 (g) by treatment of tert-butyl 2-(4-hydroxy-1-methyl-2-oxo-6-(prop-1-ynyl)-1,2-dihydro-1,8-naphthyridine-3-carboxamido)acetate (Example 83 (a)) with TFA. MS (ESI, pos. ion) m/z: 315 (M+1). 1H NMR (300 MHz, DMSO-d6) δ ppm: 12.98 (s, 1 H), 10.41 (t, J=5.4 Hz, 1 H), 8.83 (d, J=2.2 Hz, 1 H), 8.34 (d, J=2.0 Hz, 1 H), 4.14 (d, J=5.6 Hz, 2 H), 3.67 (s, 3 H), 2.12 (s, 3 H).

Sources & evidence

ORD record: ord-aeb45d62f3ef49cbbaf8333a703a3a43
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08048892B2

Reaction notes

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