Trifluoroacetic acid → HCID 86689529, compound

HRID 1853851Notes

Reaction equation

[Cl:1][C:2]1[CH:17]=[C:16]([C:18]2[C:19]3[C:20]4[CH:34]=[CH:33][S:32][C:21]=4[C:22](=[O:31])[NH:23][C:24]=3[C:25]([CH3:30])=[CH:26][C:27]=2[O:28][CH3:29])[CH:15]=[CH:14][C:3]=1[CH2:4][CH2:5][NH:6]C(=O)OC(C)(C)C.C(O)(C(F)(F)F)=O>>[ClH:1].[NH2:6][CH2:5][CH2:4][C:3]1[CH:14]=[CH:15][C:16]([C:18]2[C:19]3[C:20]4[CH:34]=[CH:33][S:32][C:21]=4[C:22](=[O:31])[NH:23][C:24]=3[C:25]([CH3:30])=[CH:26][C:27]=2[O:28][CH3:29])=[CH:17][C:2]=1[Cl:1]

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 67449870HCID 67449870, compound

Product 1

HCID 86689529HCID 86689529, compoundYield 124%

Procedure

Following General Procedure C, tert-butyl 2-chloro-4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenethylcarbamate (50 mg, 0.10 mmol) was reacted with TFA (3.0 mL) to afford the desired product as a light yellow solid (27 mg, 68%): 1H NMR (500 MHz, MeOD) δ 7.62 (t, J=5.8 Hz, 1H), 7.53 (d, J=7.8 Hz, 1H), 7.35 (d, J=1.6 Hz, 1H), 7.29 (s, 1H), 7.21 (dd, J=7.7, 1.7 Hz, 1H), 6.11 (d, J=5.4 Hz, 1H), 3.75 (d, J=7.4 Hz, 3H), 3.38-3.16 (m, 4H), 2.64 (s, 3H); ESI MS m/z 399 [C21H19ClN2O2S+H]+; HPLC 98.8% (AUC), tR=9.50 min.

Sources & evidence

ORD record: ord-1e249039e41340a88a732116d4392c3f
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08962648B2

Reaction notes

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