Trifluoroacetic acid → HCID 86689530, compound

HRID 1853852Notes

Reaction equation

C(OC(=O)[NH:7][CH2:8][C:9]1([C:13]2[CH:18]=[CH:17][C:16]([C:19]3[C:20]4[C:21]5[CH:35]=[CH:34][S:33][C:22]=5[C:23](=[O:32])[NH:24][C:25]=4[C:26]([Cl:31])=[CH:27][C:28]=3[O:29][CH3:30])=[CH:15][CH:14]=2)[CH2:12][CH2:11][CH2:10]1)(C)(C)C.C(O)(C(F)(F)F)=O>>[ClH:31].[NH2:7][CH2:8][C:9]1([C:13]2[CH:14]=[CH:15][C:16]([C:19]3[C:20]4[C:21]5[CH:35]=[CH:34][S:33][C:22]=5[C:23](=[O:32])[NH:24][C:25]=4[C:26]([Cl:31])=[CH:27][C:28]=3[O:29][CH3:30])=[CH:17][CH:18]=2)[CH2:10][CH2:11][CH2:12]1

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 123588218HCID 123588218, compound

Product 1

HCID 86689530HCID 86689530, compoundYield 138.7%

Procedure

Following General Procedure C, tert-butyl(1-(4-(6-chloro-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)cyclobutyl)methylcarbamate (25 mg, 0.05 mmol) was reacted with TFA (2.5 mL) to afford the desired product (16 mg, 80%) as a white solid: 1H NMR (500 MHz, MeOD) δ 7.66 (s, 1H), 7.55 (s, 1H), 7.47 (s, 2H), 7.34 (s, 2H), 6.04 (s, 1H), 3.77 (s, 3H), 3.47 (s, 2H), 2.68-2.54 (m, 2H), 2.47-2.35 (m, 2H), 2.31-2.20 (m, 1H), 2.12-2.02 (m, 1H); ESI MS m/z 426 [C23H21ClN2O2S+H]+; HPLC >99% (AUC), tR=9.87 min.

Sources & evidence

ORD record: ord-48858c06c67f4fefa27e7761a38562dd
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08962648B2

Reaction notes

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