Dichloromethane → 9-(4-(1-(Aminomethyl)cyclobutyl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one Hydrochloride

HRID 1853843Notes

Reaction equation

C[O:2][C:3]1[CH:12]=[C:11]([CH3:13])[C:10]2[NH:9][C:8](=[O:14])[C:7]3[S:15][CH:16]=[CH:17][C:6]=3[C:5]=2[C:4]=1[C:18]1[CH:23]=[CH:22][C:21]([C:24]2([CH2:28][NH:29]C(=O)OC(C)(C)C)[CH2:27][CH2:26][CH2:25]2)=[CH:20][CH:19]=1.BrB(Br)Br.C(Cl)[Cl:42]>>[ClH:42].[NH2:29][CH2:28][C:24]1([C:21]2[CH:20]=[CH:19][C:18]([C:4]3[C:5]4[C:6]5[CH:17]=[CH:16][S:15][C:7]=5[C:8](=[O:14])[NH:9][C:10]=4[C:11]([CH3:13])=[CH:12][C:3]=3[OH:2])=[CH:23][CH:22]=2)[CH2:25][CH2:26][CH2:27]1

Participants

Reactant 3

HCID 6344Dichloromethane

HCID 25134Boron tribromide

HCID 86689520Tert-butyl (1-(4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)cyclobutyl)methylcarbamate

Product 1

HCID 866895199-(4-(1-(Aminomethyl)cyclobutyl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one HydrochlorideYield 65%

Procedure

Following General Procedure F, tert-butyl (1-(4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)cyclobutyl)methylcarbamate (130 mg, 0.32 mmol was reacted with tribromoborane (1.0 M in methylene chloride, 1.9 mL, 1.9 mmol to afford the desired product (82 mg, 65%) as a white solid: 1H NMR (500 MHz, MeOD) δ 7.63 (d, J=5.4 Hz, 1H), 7.46-7.41 (m, 2H), 7.38-7.32 (m, 2H), 7.09 (d, J=0.7 Hz, 1H), 6.26 (d, J=5.4 Hz, 1H), 3.36-3.33 (m, 2H), 2.65 (dd, J=21.2, 9.3 Hz, 2H), 2.58 (s, 3H), 2.45-2.37 (m, 2H), 2.27 (ddd, J=17.7, 11.5, 8.6 Hz, 1H), 2.12-2.01 (m, 1H); ESI MS m/z 391 [C23H22N2O2S+H]+; HPLC >99% (AUC), tR=9.37 min.

Sources & evidence

ORD record: ord-c1f2d424833040a79630bf2bae0d0451
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08962648B2

Reaction notes

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