Trifluoroacetic acid → HCID 57331381, compound

HRID 1850809Notes

Reaction equation

[CH2:1]([N:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([OH:17])=[C:9]([C:18]([NH:20][C:21]2[CH:33]=[CH:32][C:24]([C:25]([O:27]C(C)(C)C)=[O:26])=[CH:23][CH:22]=2)=[O:19])[C:8]1=[O:34])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].FC(F)(F)C(O)=O>>[CH2:1]([N:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([OH:17])=[C:9]([C:18]([NH:20][C:21]2[CH:33]=[CH:32][C:24]([C:25]([OH:27])=[O:26])=[CH:23][CH:22]=2)=[O:19])[C:8]1=[O:34])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 67627060HCID 67627060, compound

Product 1

HCID 57331381HCID 57331381, compound

Conditions

Temperature: 0 °C

Procedure

tert-Butyl 4-(1-hexyl-4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxamido)benzoate (83 mg, 0.18 mmol) is added, in fractions, to a solution of trifluoroacetic acid (TFA) cooled to 0° C.; the mixture is left to react for 3 hours. The crude product obtained is washed with ethyl ether until a white crystalline solid forms. The product is dried to give a yield of 61 mg (83%). 1H NMR (DMSO): δ 8.16 (d, J=8 Hz, 1H), 7.97-7.65 (m, 6H), 7.38 (m, 1H), 4.27 (bs, 2H), 1.59 (bs, 2H), 1.39 (bs, 2H), 1.28 (bs, 5H), 0.84 (bs, 2H).

Workup

waitthe mixture is left
customto react for 3 hours

Sources & evidence

ORD record: ord-a13253371a5d4527a1b7b2fcdd0cbe55
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08957091B2

Reaction notes

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