Trifluoroacetic acid → HCID 68861898, compound

HRID 2099132Notes

Reaction equation

[Na+].C(OC([NH:9][CH2:10][CH2:11][CH2:12][C:13]1[CH:14]=[C:15]2[C:20]3=[C:21]([CH2:23][CH2:24][CH2:25][N:19]3[CH:18]=[C:17]([C:26]([O-:28])=[O:27])[C:16]2=[O:29])[CH:22]=1)=O)(C)(C)C.[F:30][C:31]([F:36])([F:35])[C:32]([OH:34])=[O:33]>>[F:30][C:31]([F:36])([F:35])[C:32]([OH:34])=[O:33].[NH2:9][CH2:10][CH2:11][CH2:12][C:13]1[CH:14]=[C:15]2[C:20]3=[C:21]([CH2:23][CH2:24][CH2:25][N:19]3[CH:18]=[C:17]([C:26]([OH:28])=[O:27])[C:16]2=[O:29])[CH:22]=1

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 68861511HCID 68861511, compound

Product 1

HCID 68861898HCID 68861898, compound

Procedure

9-(3-tert-Butoxycarbonylamino-propyl)-1-oxo-6,7-dihydro-1H,5H-pyrido[3,2,1-ij]quinoline-2-carboxylic acid sodium salt (224 mg, 0.58 mmol) was dissolved in trifluoroacetic acid (3 mL). After 0.5 h at room temperature the reaction mixture was concentrated to provide the title compound as a beige solid. ESMS m/z 287 (MH+). NMR (MeOD-d4) δ 8.83 (s, 1H), 8.15 (d, 1H), 7.62 (d, 1H), 4.43 (t, 2H), 3.14 (t, 2H), 2.98 (t, 2H), 2.89 (t, 2H), 2.66 (tt, 2H), 2.05 (tt, 2H).

Workup

concentrationAfter 0.5 h at room temperature the reaction mixture was concentrated

Sources & evidence

ORD record: ord-0dfd231403124123a1c0fff8e34d2506
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07569550B2

Reaction notes

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