Hydrochloric Acid → 9-[4-(Aminomethyl)phenyl]-6-fluoro-8-methoxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride

HRID 1853795Notes

Reaction equation

HRID 1853795 reaction equation
[F:1][C:2]1[C:11]2[NH:10][C:9](=[O:12])[C:8]3[S:13][CH:14]=[CH:15][C:7]=3[C:6]=2[C:5]([C:16]2[CH:30]=[CH:29][C:19]([CH2:20][NH:21]C(=O)OC(C)(C)C)=[CH:18][CH:17]=2)=[C:4]([O:31][CH3:32])[CH:3]=1.[ClH:33]>>[ClH:33].[NH2:21][CH2:20][C:19]1[CH:29]=[CH:30][C:16]([C:5]2[C:6]3[C:7]4[CH:15]=[CH:14][S:13][C:8]=4[C:9](=[O:12])[NH:10][C:11]=3[C:2]([F:1])=[CH:3][C:4]=2[O:31][CH3:32])=[CH:17][CH:18]=1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 67449397tert-Butyl 4-(6-Fluoro-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzylcarbamate

Product 1

HCID 866894969-[4-(Aminomethyl)phenyl]-6-fluoro-8-methoxythieno[2,3-c]quinolin-4(5H)-one HydrochlorideYield 90%

Procedure

Following General Procedure D-1, tert-butyl 4-(6-fluoro-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzylcarbamate (15 mg, 0.030 mmol) was reacted with HCl (2 N in diethyl ether, 1.5 mL) to afford the desired product (10 mg, 90%) as a white solid: 1H NMR (500 MHz, CD3OD) δ 7.63 (d, J=8.1 Hz, 2H), 7.58 (d, J=5.4 Hz, 1H), 7.36 (d, J=8.1 Hz, 2H), 7.32 (d, J=12.7 Hz, 1H), 6.04 (d, J=5.4 Hz, 1H), 4.27 (s, 2H), 3.72 (s, 3H); ESI MS m/z 355 [C19H15FN2O2S+H]+; HPLC 99% (AUC), tR=10.64 min.

Sources & evidence

ORD record
ord-419df252e2454131aab413d3ea4dc73d
Source dataset
uspto-grants-2015_02
Patent number
US08962648B2

Reaction notes

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